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Best Of The Best: Trails On Martha's Vineyard? Im In Serious Need Of Some Suggestions!

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Good evening!

My husband and I are heading up to Marthas Vineyard next week to celebrate our wedding anniversary! Research reveals we will be doing a lot of walking and a lot of eating :)

We like to hike and our focus for this trip is on the outdoors! My question is in regard to the many parks, sanctuaries, preserves, etc on the island. All of the trails seem really awesome but we wont have time to experience all of them (only there for 3 ½ days). I am hoping someone is familiar enough with the trails to provide some feedback as to which, in your opinion, are the best of the best. We like both strenuous and leisurely hikes and we think the coolest hikes are those that incorporate various ecosystems.

Also, I was kind of excited to head over to Chappaquiddick for one of our 3 days (for more trails)-do you think this is wise or do you think our days are better spent on MV? In an earlier post another user did suggest we head over to Chappaquiddick, however, I hadnt mentioned that wed only be in MV for 3 days...

Thank you SO much for any feedback youre able to provide! I may bump this message a few times over the next week or so before I leave as Im so eager to get your suggestions-thanks in advance for your patience!

Have a pleasant evening!

Sincerely, Carrie

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    Just heading to bead and you hit me with this question. 2 years ago, we finally hit MV for a week, in June before the tourists. I LOVE Chappy!!! If I return, I would stay there and take the ferry to dinner a couple of nights! Stop by Chilmark Chocolates if you're in the neighborhood, as special need kids make the chocolate more than special!

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    We were in MV for 10 days in August: our 3d trip there but the first time we went to Chappy. I would VERY highly recommend going. Pack a lunch.
    Head to Wasque Reservation: gorgeous dunes and beach for walking or fishing. Consider stopping at the Japanese Garden on Chappy (it has a more specific nname, but everyone will know what you are talking about). Of course, it is hard to go wrong on MV. Have a great time.

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    Thanks gyppielou and hagen22 for the responses! "Chappy" is now on the must-do list! And thanks hagen22 for the Wasque suggestion!

    Does anyone have further input on their favorite trails on MV? There are so many to choose from...Thanks in advance!

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    We've spent every August on the vineyard for years and we also hike/walk/kayak/etc. I suggest you visit the web site www.thetrustees.org - the site is run by the trustees of the reservation and on it you can click on properties, choose cape cod and the islands, and look at what is on MV that might appeal to your tastes - I believe you can even download trail maps, etc. and confirm what is open off season and what activities if any are running and times open (most close at 5pm) You can look specifically at ones I mention below. you can also email islands@ttor.org with questions, etc. If you are not a member, some require small admittance fee - don't know if you will have a car - if so, I would also suggest some other places - are you renting car? Are you planning on driving out on beaches where it is allowed (like out to light house, etc) or just interested in walking - let me know and then there are other recommendations.
    Are your three days three full days on island not counting travel days? If you have 3 full days you will still have choices to make but the web site, or some info from me might help you narrow your choices depending on interests so you don't do two trips that are similar vs. seeing variety. Also, where are you staying? If in Edgartown it might be w/in walking distance to Chappy Ferry, etc. so location would help also. Also, where are you coming from b/c if Massachusetts, you might even consider joining Reservation of Trustees b/c they have sites all over the state. You can visit their office on island to do that if that is a choice for you since you probably wouldn't receive membership card on time in mail.
    I would plan one day for Chappy - take ferry (it's a one minute ferry ride-you could swim it it is so close) - if you have off the road rental, you should take car BUT you will not be able to drive off road on dunes, etc w/out a over-sand vehicle sticker which is very costly for just a 3 dy trip - (I think about $110?) if not, you would need rental bikes as it is long walk from ferry to interest points on Chappy and in that case I would just take bikes to ferry and not pay for car over and back but minimal pedestrian fee. It's a great place to bike. pack lunch as Chappy has zip in regards to eating places, etc. Get map either from web or once on island and if you follow only entry road you will see visitor center on your left and can get maps there (and restrooms which are rare, unless porta potties are still at beach entrances) - which is also where the Japanese style garden mentioned is Mytoi and it is lovely. It is open yr round and takes about 1/2 hour to visit. No admission fee. On Chappy is Cape Poge Wildlife Refuge, (barrier beach, beach grasses, dunes, tidal waters, salt marshes, etc. - they also offer open vehicle tours to the light house over the sand and out to the point that is an option for you if you don't have over=sand vehicle permit and will get you much further out than you would by foot. I don't know how often theyu run off season, but probably on the web site oremail them. Also on Chappy is Wasque, glacially deposited land form with footpaths, bird watchers love this spot. Also on Chappy are Norton Point, Poucha Pond, Five Corners Preserve, North Neck preserve. I suggest a day on Chappy to enjoy at leisure biking, walking, etc. ocean on one side, lagoon on other, don't know if off season they still have kayak rentals but kayaking is splendid out there.
    Another day would be going to Menemsha Hills (longpoint@ttor.org) on North Road heading toward Chilmark (where the chocolates are) - you could do this by bike but the road is long and bumpy so you may end up walking bike at some points and be on lookout for cars as road is narrow and windy. calling card here is several ecosystems w/ different topography - there is parking but only for about 15 or 20 cars, but that shouldn't be a problem off season. you walk all the way out to water, nice views at end. (figure 2 hrs). after that, you could continue towards Aquinnah/Gay Head area and that lighthouse and walk Moshup beach where the clay cliffs are - this is alovely beach to walk and yes, it is the one that leads to the nude beach but in Oct weather who knows, but just warning you in case that is an issue for you. I think the restaurant on top closes by now, but maybe not.
    When you reach near lighthouse you will see parking area on left and there is a path in middle of parking area that leads to trail to beach (in case lot is closed, there is angle parking near restroom.
    This is a long bike ride, so that is up to you. Or , there is bus on island that can take you up there if it interest you. On the way you will go thru Chilmark and some lovely, less developed areas of island. Also tons of galleries/antiques/etc but again, some are open even in the summer odd hours.
    If time, on way you could stop in Menemsha harbor which is adorable, with a handful of luncheon spots and stores, but again, they may be closed by then.
    But sunsets from here are magnificent at Menemsa Bite.
    Also look into Long Point Wildlife Refuge, which is off Edgartown-West Tisbury Rd and is easier bike ride from Edgartown area (but again don't know wher eyou are staying). You could also bike past South Beach, and walk that, it was closed this summer to off=road vehicles, but you can walk and if you ask you can find Mels Diner wher ethe glider planes take off from and stop for a breakfast or lunch or rest. Many entrances to these areas are very bumpy sandy small roads and you might end up walking a bike.
    Depending on your location, I could recommend some restaurants depending on if you have car or will be using island bus or cabs (which have gone up considerably this year b/c of gas, etc), places if you like music/jazz/dancing/etc/where to get sandwiches, etc.
    If you want some ideas, let me know. Also if you want rainy day ideas, which I hope you won't need.
    There is also a reserve w/ small animals and lovely walk not far from Edgartown; and it is always a nice run/bike along State Beach with ocean on one side and lagoon on other. There are not too many strenuous hikes on MV, most are easily done. But since things might be closed, which you will find out either prior on web site or on island, pack a lunch/snack/waters. Hope this helps and if you want to answer any ? I posted in this to you, I will check back.

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    Hello escargot!

    First Id like to tell you how much I truly appreciate the time and effort you took to leave me such a lengthy and detailed post!

    Also, Ive tried to do a lot of research on my own before I posted some questions so maybe I can share my tentative plans with you and you could provide your own opinion? First I will answer some of the questions you posed:

    We are bringing our own car but Im not sure how it will do on some of the terrain (its an old Volvo).

    We are driving up from Pennsylvania (will post route for fodor feedback later tonight). We are leaving PA very early Thursday morning to arrive at the ferry around 2. We are staying three full days (Fri, Sat, and Sun) and returning on Monday.

    We are staying at the Sharon House in Edgartown which is on N. Water Street. The map seems to suggest its near a beach (or maybe just a shoreline)-do you know if its a beach we can walk to/relax on?

    Im debating whether to bring our bikes-I want to but my husband thinks it will be too cold to ride around. I think well end up throwing them in the car though just b/c it seems like such a nice way to see the islands. Id love your thoughts on biking the island at that time of year.

    Im almost positive we wouldnt do the off-road rental just b/c, like you said, I researched and found out about that charge. It would be cool but I dont think we can swing it this trip!

    Research has also revealed Menemsha as “thee” place for sunsets. I totally dig sunsets so that will be a sure thing! Is Menemsha Bite different from Menemsha Beach?

    The nude beach is kind of funny-I dont have anything against it but its always nice to be prepared to see something like that-hahah!

    I like what you say about the small reserve in Edgartown w/ the small animals-would that be the Sheriffs Meadows Sanctuary?

    I typically love cozy rainy days but Im sort of hoping it holds off while Im on this trip-I would LOVE your input for how to spend a rainy day though just in case! Im pretty much open to any suggestions except that I dont really like to look around at shops.

    I researched probably like every restaurant on the island :) Im vegan (can get by as vegetarian) so no meat/seafood of any kind for me and my husband doesnt like seafood but is otherwise a carne-lover.

    The places we thought sounded cool (places to gather info/brochures, neat things to check out, food, hiking) are on the list below. The list is compiled from internet and book research and topped off with Fodor website and Fodor travel guide research. I would be grateful if youd offer your opinion on some of the things on my list! The notes in the parenthesis are just things to remind me of why I put them on the list!

    VINEYARD HAVEN/TISBURY
    -Marthas Vineyard Chamber of Commerce (maps and brochures)
    -Black Dog Bakery
    -*Black Dog Tavern (atmosphere)
    -Centre Street Cemetery
    -West Chop (“exclusive air/distinguished residents" Main Street)
    -West Chop Lighthouse (scenic overlook)
    -Zephrus (chocoholic platter)
    -Cronigs Market (local farmers)
    -Island Cove-putt putt
    -Art Cliff Diner

    OAK BLUFFS
    -Information Booth
    -Oak Bluffs Campground (gingerbread houses)
    -The Tabernacle
    -Sweet Life Café (good for dessert)
    -Linda Jeans (breakfast)
    -Offshore Ale (dinner)
    -Good Dog Goods
    -Jimmy Seas (Italian)
    -Joseph Sylvia State Beach (good view)

    EDGARTOWN
    -Marthas Vineyard Historical Society
    Edgartown Visitors Center
    -Espresso Love
    -Sheriffs Meadow Sanctuary
    -Felix Neck
    -Morning Glory Farms
    -Hideaway Lounge (drinks)
    -Murrays (shopping)
    -Lighthouse Beach (good view)
    -Little Beach (little known beach)
    -*Among the Flowers
    -*Newes From America
    -Edgartown Pizza
    -Mad Marthas (dessert and sandwiches)
    -Fiesta Mexicana
    -Laitanzis Pizza
    -Edgartown Deli
    -David Ryans
    -Chappaquiddick

    WEST TISBURY
    -Polly Hill Arboretum
    -Alleys General Store/Back Alley Sandwiches
    -Old Oak Tree (cool tree)
    -Sepiessa Point Reservation
    -Long Point
    -Tisbury Meadow Preserve (hiking)
    -Ripleys Field Preserve
    -Wompesket Preserve
    -Mayhew Chapel and Indian Burial Ground
    -Cedar Tree Sanctuary
    -Manual State Forest
    -Biga Bakery and Deli
    -Lamberts Cove Beach (fine sand, clear water)

    CHILMARK
    -Waskosims Rock Reservation (trail)
    -Abels Hill Cemetery
    -Chimlark Chocolate
    -Lucy Vincent Beach (most beautiful)
    -Squibnocket Beach (pebble beach w/ marine life)

    MENEMSHA
    -*Menemsha Beach (sunset)
    -Menemsha Hills Reserve
    -Great Rock Bite Preserve

    AQUINNAH
    -Aquinnah Cliffs/Moshup Beach
    -Aquinnah Springs (water to drink)
    -Cranberry Lands (cranberries gone wild)

    And to think-this is my whittled down list! As you can see, there appear to be tons of hiking and nature activities-which is awesome! But I cant for the life of me narrow them down. After I post this Ill check out some of the websites you recommended to choose some cool trails. The things with * next to them are things I really want to do. Like the night we get there is our anniversary and I think the Newes From America is where well go b/c I like the description of the atmosphere!

    Again, thanks for the great information you posted for me-I hope someday I can give you helpful information about one of your destinations!

    Very Sincerely,

    Carrie in PA

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    Oh, oh oh....I had the Best Fried Clams of my life.....and I've had a lot, at help me someone - that place on the right in Menemsha - it's in a cookbook, first syllable? sounds like? and that fantastic scupture down away. Head to Larsons for some oysters or a steamed lobster on the beach...and head to this other place for yummy fried clams! Some cute shops too! Yet still, make Chappy remain a priority! Fun!

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    Be sure to stop over and pick up something from the Black Dog store... Something with the famous black lab printed on it, maybe a coffeemug/frisbee/apron/tshirt/ballcap/mousepad. They make great father's day/birthday/Christmas/Kwanzaa/graduation gifts!!

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    Ok, here's what I think. Honestly you are not going to be able to do everything unless you run wild from early am to dark. As a thought, let me say the beauty of the vineyard is enjoyed at a leisurely pace - relax, laid back, easy - which is why we love it so much - as casual as you can be with clothes to match that mood. You can see plenty in your 3 days, and while you won't see everything, you will see enough to get a wonderful taste of everything you love and hopefully return. While there are many of the lovely beaches, vistas, hikes - I would rather you see some of everything and not four hikes that are similar. That being said, here are the answers to your recent ?'s and an answer to each of your itinerary questions.
    You are driving: do you have a car ferry rezzie? It may not be the busiest time of year, but a rezzie is always nice in case a ferry is full. (steamshipauthority.com) you would take from woodshole, unless you come through RI in which case you can take it from a location there. If you have to go to WoodsHole, then I can help you from Boston there when you post drive plans and tell you there is major construction going on near Sagamore and Bourne bridges that even on a Thursday, depending on what they are doing, could delay you 20-60 minutes. (you can also check this live on traffic.com before you leave for updates if you are nervous type) In another post I can send you directions from the bridges of way I feel is easiest.
    Your old Volvo will do fine on the dirt roads leading to the trails, everyone has to drive slowly over them, but you will be fine.
    Good you are staying in Edgartown. Sharon House is on N Water Street as is Lighthouse Beach, which is off N Water near center of town, also known as harbor beach at Starbucks neck.
    However, you can also access beach by taking ferry on foot across to Chappy and walk to your left. later on that.
    Bringing your bikes: it can be cold in Oct/ once you get going on bike and if you do long ride up to Aquinnah/Gay Head - well last my niece did that she ended up hailing a ride w/ a pick up truck she was so cold. BUT you could do that upisland part by car (which would also get you access to a few nice hikes on the way down those bumpy roads) and even if cool, you could bike in other areas around Edgartown for shorter rides, and you'd have them if you get warm, sunny day. ie: it is not a long ride to go from downtown Edgartown (Edgartown is small, you can walk the whole thing in no time, so biking out of there and onto street is nothing. There is walking path and/or bike (out of edgartown, pass stop and shop supermarket to "triangle" in road, bear right, and you can bike all along Joseph Sylvia State Beach (state beach) with ocean on one side and lagoon on other it's about 2-3 miles to Oak Bluffs -
    lovely bike ride if good day. Also you could bike to State Beach, Morning Glory Farm, Mels Diner, etc.
    Other than that, unless gloriously warm day, I think you'd be cold doing the long long bike ride to Aquinnah/Gay Head. So, maybe throw them on the car and if you use them great, and if not what's the harm. Also if bikes go on top of car, remember height restricitions on ferry on ferry (height and length) you can take higher, longer, b/c we do with kayaks, but they need to know ahead of time if it is above listed heights/lengths to plan for how many cars they can accomodate. Also remember, unlikely island will be incredibly warm early am./ might have some fog/ and better warmer time might be nearer noon when you are already off somewhere unless for one of the smaller rides listed above. But i think bike would be ok on chappy, but you'll see more faster in a car on all the trips, with still plenty of time actually hiking/etc. so some things to consider. i don't feel I can make that choice for you, but if it was me, I'd probably lv bikes at home unless it is incredibly easy for you to bring and you won't mind never using.
    OK, no off road rental, no need if you are bringing own car and if you want, as I said, you can take that tour in chappy out to the point, and that is all the off roading you will need (to the lighthouse out at chappy) I do recommend that to get a feel for what you see off roading and they will take you all the way to lighthouse, past dunes, ocean, interwater ways, etc. Don't worry about getting brochures at every town, you can get at main trustee place/downtown edgartown and pick up local mv paper on what's going on that week it usually has a huge map of island and beaches in the middle; except at chappy they usually have good map at visitors ctr.
    From your list, here are my comments:
    Vineyard haven/Tisbury
    Black Dog Bakery: it's a "tourist" landmark. I don't particularly think their coffee or baked goods are so great; but usually every guest we have wants a black dog t shirt, etc. Art Cliff Diner is nice, and some of our family love it, but I feel food portions are huge - in the summer it can get stuffy but is good for rainy day. There is another coffee/breakfast place a few doors down from it heading out of vineyard haven towards the bridge to oak bluffs area and I like that better. fresh, lighter, has good coffee, newspapers, etc. good place to begin the day going off to vh or up island. (it is across from Net Result seafood in parking lot- across st from gas station) and I have total block on the name at the moment.
    Black Dog Tavern is good for dinner, remember to byob b/c VH is a dry town. Zephrus also good, but you might want to save for lunch on a rainy day. If you go to Z for dinner, you can byob or they will arrange for liquor store to deliver as most dry restaurants will. Cronig's Market I would not personally go to for local farmers, esp in october, is is a supermarket that carries some local produce but better to save that experience for Morning Glory Farm. Island Cove, yes if you want to play mini golf. I think you can do that anywhere so unless you are fans or desperate I would skip. You can drive by West Chop/lighthouse/cemetery in no time.
    Oak Bluffs:
    Yes do the OB campgrounds. you can drive through right to Tabernacle, but if you have time walking is nice to really see the houses. Sweet Life Cafe is expensive and maybe you can go just for dessert but not if they are full and I doubt they are using garden outdoor dining still, but you can call. They also own a lunch place in OB called A Slice of Life which has great fried green tomato blt's and you can get w/out the bacon! also great pannini sandwiches, etc. just as an fyi. good for rainy day lunch or to take on ferry also. Ofshore Ale or Jimmy Seas are fine. Also in OB is Giordano's for italian or pizza and Zapotec for mexican. Maybe you can eat dinner elsewhere if you want to eat in OB and then do sweet life dessert, call and see.
    Also, in OB is old merry go round but don't know if still open. Good dog Goods is cute shop with all dog stuff (you must have a pet :)
    Edgartown:
    Sheriffs Meadow/Felix Neck nice: Felix Neck often has great tours (some sm animals depending on what they have at time) this should be listed in the weekly MV paper I mentioned before. Morning Glory farm a bike ride or car drive out of downtown but yes, and lots of pumpkins in fall and if they are still baking they make the best muffins and homemade bread and you could probably find things there for snacking. Murrays for shopping (that's the "nantucket red" store) so if you want t's or something, and there are lots of other t shirt stores downtown to check prices. Murrays can be pricey maybe depending on what you want to spend.
    Lighthouse beach mentioned before. Newes from America I think you should check menu on line. I don't eat there often, pub style for me and I remember it being lots of meat and sandwiches and not much for vegans but you can go to www.kelley-house.com/dining.shtml and see menu and decide. also use the site www.mvol.com - good source for restaurants/menus/events on dates you will be on island. Lattanzi's has an italian restaurant and a separate pizza place connected in downtown Edgartown. both are good. Deli/sandwich shop across from it on patio is also good. David Ryans good for nachos, salads, etc and drinks, younger crowd. Chappy a definite day.
    West Tisbury:
    Polly Hill Arboretum is lovely, Alley's is a cute general store, Long Point I mentioned in original reply to you, Chapel and Burial Ground good stops, Lamberts Cove is private beach, don't think you can get on, maybe off season but gate might need key.
    Chilmark:
    Abels Hill is nice, Waskosms, Chilmark Chocs (sometimes weird hours but you can often get in other lcoations) Lucy Vincent Beach is private also as is Squibnocket. usually you need key to access entry and/or resident sticker only. They usually let only owners and owner guests or rentors in with proof. The residents surrounding the private beaches are very proactive on keeping their beaches private. Lucy Vincent/Squibnocket are lovely, best beach for when kids were little, but you will see other gorgeous beaches. Other priv beaches are Lamberts Cove, Lobsterville, etc w/ restrictions. check it out on www.mvy.com/islandinfo/beaches.html
    Menemsha:
    yes, best sunsets. Menemsha bite place to eat, again don't know what is still open down there so find out before you plan on eating. mostly seafodd at the outdoor places. You might want to bring take out w/ you or just a bottle of wine and sit on rocks and watch sunset and then go to your dinner elsewhere b/c I think it will be cold to eat dinner out there at sunset.
    Aquinnah:
    yes, clay cliffs are beautiful - red, gold, brown, white and don't take any clay or mud with you! not allowed! but great walk and if you walk far you will be able to look up and see lighthouse on top from near where you started and if nude bathing, i have always found everyone out there to be very private and unassuming and friendly should you choose to chat about something you see, view, waves, rock sculptures people are building, etc.
    My opinion, I would try and build your days like this: and keep the driving day for an iffy or bad weather day.
    You should be settled at Sharon House probably by 4pm. If you need directions from ferry to there let me know. You could walk Edgartown a bit and get our bearings, pick up newspapers, tourist maps, etc and (oh, it's late my memory) there is a lovely new tea shop (Sharon House will know to tell you how to walk there) owned by lovely English couple that serves nice tea, bisquits, scones, etc if you want a little something and sit and look over your stuff and talk with them) Or, go to David ryans, sit at bar, have a drink and talk to bartender and look over your stuff. There is small pharmacy diagonally across form DRyans that will have papers, maps, etc. and Sharon House might also. Check out the menu at Chesca's in downtown Edgartown. You don't have to go for a full courses meal and you might find some things to eat there, the food is exc and the fresh hot bread a dream. If it is nice out they have nice rocking chairs on deck, art galleries next to it, sculptures on patio, nice bar. Check it out b/c you might rather eat there instead of Newes for special night.
    You can also walk by and see menus at lattanzi's restaurant, the pizza part, DRyans, Newes and choose where to eat that night. All w/in a quick 10 min loop of a walk or less. If you are in the mood for music, call Lola's in OB and see who is playing, it's about a 10 min drive or less from Edgartown and a fun place. Anything goes at Lola's, everyone's casual, everyone dances wtih whoever they want, girls w/ girls, guys w/ girls, couples old and young and all types. sometimes greaet bands or save for another night you might be tired!

    Day One: have breakfast (does Sharon House provide?) if not, anywhere in Edgartown for a quick bagel, etc: the deli downtown next to Scoops ice cream (oh, another memory word finder block) on Main St. Get lunch /water to take with you if weather good, and make this your Chappy day. Take either your bikes or car over on ferry. You will do more in the day w/ a car even if weather good. Off ferry,, straight ahead until you see visitors ctr on your left. Get all info there. See the japanese garden even if you do a 10 min walk thru.
    See about tour to lighthouse and what time might work for you, or better yet call ahead the day before for times so maybe you can make first one. Then, when they bring you back to visitors ctr, take off on your own to the places I mentioned first post and just explore and have fun. You will walk a lot and see a lot of what you say you like.
    Ferry back and go to dinner at either OB, one of restaurants you mentioned, or at VH and maybe to Lola's or wrap the night with a drink back in Edgartown.
    Day two: Also good weather day: Take car, and drive along State Beach to OB, breakfast is breakfast, so I wouldn't waste time on that andwould grab a bagel sandwich/muffin/coffee in OB and just keep driving) it's small area, you will find everything. At end of beach drive when you see ferry dock, take left, park near carousel and u will see coffee/breakfast places/Linda Jeans/etc. Then drive out of town, but take the right at general store/market and that will take you along the shore on east chop drive, past the lighthouse (sister lighthouse to one on other side of chop), when you finish take a right, take next right, over bridge into VH. (or wait, and eat entering VH; coffee shop across from gas station after bridge, art cliff next, black dog next) - at intersection go uphill and head up island towars Aquinnah/gay Head. You will drive Tisbury/(pass Cronigs, mini golf, etc) and just follow signs and I would go straight up to Aquinnah/Gay head and do the Moshup beach walk and lighthouse earlier in day (the drive up will be about 30-40 min and the walk on beach about 90) then head back down island and do stops/ hikes on way back and that way you can hit all the other stuff on way depending on weather - on way back you can decide about Polly Hill, Abels, Chilmark Chocolates, the hikes I mentioned earlier, trustes of reservation hikes, etc. and plan so you make Menemsha at sunset. check timing for sunset in local paper. Check before you leave at Sharon House that Alleys/Deli/sndwich shops on the way are open and if not bring lunch/waters w/ you. Be careful following signs b/c you turn different to head up island and follow signs up or back, depending on what you decide to Menemsha.
    you will only have great sunset if sky clear, so that might depend on how you plan day. End of day, choose to eat OB, VH, or Edgartown, there is movie house in Edgartown, and places to have drinks (Dryans, etc) or make this your special dinner night.
    P.s. If you can't make menemsha sunset, it is also pretty from west and east chop and otehr areas.
    This will give you day of hiking, walking, beach, and whatever other stops you choose if you see cute galleries, antiques, menemsha village, etc even if you don't stay for sunset. sunsets, as usual, are best on clear days/nights so that is up for grabs in oct. Read about your choices, look up hikes on trustee web site, arboretum isnice, but it isn't a hike down to the water and thru the woods/etc. depends how much you like arboretums and gardens vs. beach walks andhikes. You dn't want to have to do the upisland drive again, so make it one good long day.
    Day Three: Breakfast wherever: Explore OB. Do the gingerbread / tabernacle area / when you enter from that beach road and see ferry dock, take left again and pass gas station and nancy's restaurant and park along water on left. cross st to gingerbread house/tabernacle entrance and walk or drive. walk up circuit ave (the main st) see sweet life cafe, good dog goods, etc, look at menus) and head into VH again and walk thru that downtown if youwant, do cemetary, west chop, lighthouse, etc and then head back towards edgartown adn do the morning glory farm, (or start w/ morningn glory farm and do this in other direcction) - south beach, do the trsutee hike on that side, maybe felix neck, etc. and head back to edgartown.
    Shopping in edgartown you can fit in anytime. it's shopping. grab your t shirts and spend your time hiking/driving/walking/beaching.

    Athis is my suggestion and you can fine tune the itinerary to your individual hikes/choices.
    See what you think and I hope I haven't confused you. I'll check back to see if u have questions. You will love MV and want to come back for more. Save Nantucket for another time, I don't love it the way I love MV, but it has its spots. But not on a day trip taken away from MV.

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    I think escargot covered almost everything, but a few additional suggestions, if they aren't in there.

    During the summer season, the trustees of reservation ran jeep tours out on the beaches on Chappy. this is one way to get around the off-road access issue...go with someone else. I've never done one but I think it would be fun. I have gotten and off-road permit and driven the beaches, and for sure Wasque and Cape Pogue are beautiful.

    Other restaurant suggestions in Edgartown: you might try Alchemy or Atria. Both are excellent. I'm not sure if you'll find vegan entrees or not, but they are worth checking the menus. Also, I second the suggestion of Chesca's. And you should definitely have a beer at the Newes, but I'm not sure its the best place for dinner.

    have a great trip!

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    Interesting info about Martha's Vineyard. It's a place my wife and I want to return to. We were an engaged couple from Iowa there in summer of 1952, at a student seminar including day jobs in Edgartown resort hotels. Are either the Harborview or Colonial Inn still operating by chance?
    ozarksbill

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    Yes, harborview and colonial still there - you should come back ! and it is still a destination for college kids from everywhere to work everywhere.
    As far as Alchemy and Atria : Alchemy is lovely for rainy day lunch at bar from bar menu/ dinners are good, I was disappointed past few years and did not go at all this season. But that could be me, b/c menu has had some changes and I do not eat fish and very rarely meat, so there was not much for me to choose from. Atria food and decor excellent but I did not mention b/c it can be well over 150 couple with drinks, full dinner, wine but you can go for food and do w/out extras but their cocktails I thought were ridiculously expensive. You can walk to it from downtown edgartown. I mention Chesca's for you b/c it is in downtown, you can eat more reasonably, they don't mind you sharing appetizers/meals/ and there is more to choose from on menu. But you can walk to all of these and check out menus/prices yourself. I agree w/ china cat about Newes - check it out and see what you prefer, so much is individual tastes on restaurants, fun to have a drink there maybe, or for a rainy day lunch perhaps, I just didn't think it was a "special" place for celebrating. And save room for Mad Martha's ice cream some day/night but it is rich and creamy so one scoop is enough for me. Richardsons ice cream in OB is good too.

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    Too cold for bicycles? Never, unless you're getting a freezing rain! If you can hike, you can bike. Bring them.

    I wish you a great weekend but fail to understand "best of the best" requirements. MV is great; enjoy what you see. No one's ever been disappointed to see the "Mona Lisa" because they didn't see the "Last Supper" now have they? Nor will you in selecting MV things. In fact, missing some will be incentive to return!

    Enjoy!

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    Hello escargot! Thanks for second truly informative post!

    ANSWERS TO YOUR QUESTIONS:

    I made the ferry reservation (us and car, bikes inside car to avoid additional fee) in Jul so hopefully Im set with that.

    Getting from ferry to Sharon House I had planned on us just “figuring it out.” Please dont feel obligated to post those directions as youve provided me with so much information already!

    Theres no (included in your price) breakfast at the Sharon House for off season.

    Ive not heard of the Black Dog until I began researching MV. I will skip the bakery (thanks for that input) and do the tavern for dinner-I like the descriptions of the atmosphere and view.

    QUICK FINAL QUESTIONS:

    I think well be getting our lunch to go all 3 days as we hike around-do you have a particularly favorite hoagie shop? Ive assumed wed go to Edgartown Deli just b/c its right there but Ive read mixed reviews. This isnt a huge deal, just wondering if you had any favorites…

    Is there any wireless internet access on the island?

    Is the English tea place you recommended possibly the English Butler?

    This is the first time Ive ever tried to plan an itinerary and Ive worked really hard on it and much thanks goes to helpful Fodor responses to my posts!

    At first I wanted just a relaxing and romantic getaway (from school, mostly) but then I got all tangled up in details and trying to see it all. Escargot and my husband reeled me back in to once again focus on relaxation!

    Im so excited and Im sure it will be great! Thanks again for all your help!

    Sincerely, Carrie

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    There is wireless internet access on the island at libraries. Oak Bluffs, Vineyard Haven, for free - they have computers, - or you can bring your laptop and even get the signal from the car parked outside the OB library. (top of Circuit Ave, the main street/hill where sweet life cafe is) VH is a nicer library area downstairs for internet access. Cell p hone service is also pretty good, except you lose it on the way between CHilmark/Menemsha/Aquinnah but I ahve rec'd cell service if I stand in a spot at Aquinnah and don't move a hair, but you can still lose signal in middle of conversation. just an fyi.

    You say you made ferry reservations and hopefully that is all set - but - If you made ferry reservations you should have a boarding pass you rec'd in the mail; if you have not rec'd then log on to steamshipauthority.com or call them and find out where it is. you need it to board. and check and see if you paid for the passenger in the car, b/c if you didn't it is not a problem, just someone run in to the terminal when you get in the car ferry line and buy one.

    Sandwiches to go: yes, edgartown deli is ok,, but I prefer Shiretown Meats - when you leave Edgartown heading out towards the "triangle" (ask at Sharon Inn) before you get to stop and shop it is on your right. you will see the sign in the window of the small white cape looking bldng, you can use same entrance for supermarket, just bear right. They make sandwiches to go while you wait, all types, and have great pickles ! - drinks/chips/some fruit/etc. You might want to bring w/ you a small cooler type soft bag to keep things in in your backpack.
    You also might want to call Shiretown and make sur ehe has food for vegetarians, he may not. Or, you can probably go in supermarket and look for veggie options. Also, depending on teh day and where you are headed, Mad Martha's in edgartown has some interesting sandwiches so you can check out that menu when you walk around and get your bearings first afternoon there. There is also a cute little place, (another name I can't remember) - but if you are at Mad Martha's walk towards Chesca's from there, not toward the end of the street w/ the pharmacy and you take your first right, it is on the left, tiny place, good food - cafe style, you might like that palce for sandwiches or light lunch/very casual dinner. we ate there a few times this year before a movie. You can also pick up sandwiches in Oak Bluffs at A Slice of Life, or at the bagel shops, or on the road up to Aquinnah/Gay Head, you will pass Cronigs Grocery Store, another Black Dog, and several sandwich places further up, but I find them very expensive in the Chilmark area. Food even in grocery stores is expensive on island, if you like granola/power bars/etc I would put some in the car along w/ a case of H2O or your preferred drink instead of paying island prices for that stuff.
    English Butler must be the place, in Edgartown. A quiet spot to sit and relax.
    Also, in one of your posts it stuck in my mind when you were asking about beaches to sit/chill on - at the end of most of the hikes I mention in first post you end up at a beach/cliff/water view and can sit and chill there before hiking back.
    Anyone at the ferry landing can tell you how to get to Edgartown, - different if you land at Oak Bluffs vs. vineyard haven,, but I don't mind giving you directions, they are quick and easy and I would take you the scenic route, so if you want let me know.
    I did post on your direction requested post about merritt vs. 95 for that part of your trip.
    Rainy day options: oh well, they are about the same as rainy day options in any cape/island area. it isn't a city, there aren't museums, etc to duck into for a half day or whole day. But if it isn't pouring, take your rain coat and head out in the car anyway and this could be the day you drive thru Oak Bluffs (go the dog store you mention, eat at Slice of Life, walk through the gingerbread area/tabernacel and go to VH, walk thru stores, book store, have a drink, go to lunch in edgartown, see a movie, or drive towards aquinnah and hit some antique/gallery type things and if weather clears, head for one of those hikes anyway. eat, drink, read, look thru bookestores, nap, etc.......I am hoping for good weather for you. any other questions post, i will check back until you are off and on your way.

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    by the way, we stayed at the Sharon House last winter and I thought it was quite nice. The room was a little small, but very pleasant and the innkeepers were helpful. They have a neat looking outdoor hottub that was even available in February! we didn't use it, but that would be nice to have after a day of hiking.

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    Hello and good evening escargot!

    I would appreciate the scenic route from the ferry to the Sharon House-were arriving at Vineyard Haven. Thank you very much!

    Thanks for the hoagie shop info, also!

    I did get the boarding pass in the mail-it says 1 car and 2 passengers so Im hoping that goes smoothly.

    Thats great that theres internet access b/c Ill have the world at my fingertips just in case I need it! Plus, unfortunately, I have to do some junk for school. Ugh.

    That was a GREAT suggestion about bringing the case of water-I would not have thought of that!

    I just thought of something as I was preparing to pack-what should we wear to places like NFA and Chescas? Are jeans or cords ok or is it dressier?

    Im so printing this thread out minutes before we leave b/c youve given me such awesome information-I cant tell you how much youve helped me plan a cool trip and I wish I could do something in return to thank you! Of course, thank you to the other posters as well-everyone has been helpful!

    I did get your directions and Im taking the route Shanty suggested (which you and some others also thought was best).

    Hi China_cat! When I was researching the Sharon House I wasnt able to find out a whole lot. I was deciding b/w there and the Mansion House-I chose Sharon House b/c they gave me a better deal. The room does look small-its like all BED! I just want it to be cozy and clean. I cant wait to use the fireplace and the hot tub! How are the bathrooms? Plain and small? Big and marbled? Somewhere in between? Thanks!

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    You are all set w/ your boarding passes. you will just show them to the ferry guide as you enter ferry line and he will tell you which ferry line to get in in parking lot and you can wait in car until ferry comes, or if you get there early, stretch your legs, rest rooms, etc in ferry terminal.

    Dress is very casual on the vineyard. I wear jeans almost everywhere, have worn them at Chesca's but with a nicer top than I would to a pizza place, if that makes it clear. Jeans w/ flip flops and a tee shirt to one place, jeans w/ nicer sandals/shoes and a nice jersey or sweater/jean jacket to Chesca's. Newes is very casual. If you want to wear corduroys or nicer pants, that is fine too. you will see verything on the mv, from funky to casual to classic, but mostly casual. There are a few (and I mean a few) restaurants where you'd need dressy, but I don't think you'll end up there - i wouldn't bother. enjoy the real mv.

    Directions: There are really 3 main roads that connect you to all ends of the island. From VH Ferry you can go the inside road or the shore road, I always go the shore road between VH, OB and Edgartown b/c if I am there, i want to drive past water, not trees on either side of me. The difference in time is maybe 3 minutes, and I'd rather have scenery. Plus, t his will take you by some sights you might be going to and help you get your bearings and distances between things, and the whole ride from ferry to inne should be about 15 minutes, so stop along way if you feel like it looking at a view or grabbing a cup of java

    From VH Ferry: Take left out of parking lot-
    (You will pass supermarket on right, Black Dog on left)- to intersection and bear left -but not hard left)-onto the Beach Road

    (so Deli/Cafe is on left, t shirt store on right *don't go straight which would have t shirt place on left and Post Office on right *If you went hard right you'd head up to VH center and road to Tisbury with Vineyard Haven rd on your left, which could also take you to Edgartown but is boring road. *if you took hard left you'd be in parking lot for Black Dog)

    So (aside from all that) take that left at intersection right after Black Dog and
    follow Beach road - you will pass Art Cliff Diner on right, Net Result on right, Winds Up rentals on right, and go over the bridge, so VH harbor where you just came in on ferry is on your left and the lagoon on your right. Lovely.
    (As you just come off bridge glance to your left for entrance to Eastville beach; you can always bring car in there and sit there if you want sometime and watch ferries go by, etc , enjoy a cup of java or whatever)
    Road will then bend sharply to right, past the Main Entrance to MV hospital, and after bend you will be taking almost an immediate left onto Temahagin Rd (you will see hospital emergency entrance up ahead on your right, if you go by it, you missed the left).
    You will pass State Police house on right, and houses and harbor on your left.
    Road will bend again sharp right - DON"T take that right onto New York Ave, instead take a left onto East Chop Drive (just be careful b/c cars are zipping around that corner). NY Ave would also take you into Oak Bluffs, but it's a non descript road.
    So you take that left onto East Chop Drive/Highland Dr instead and you will still have VH harbor and ocean on left, will pass the east Chop lighthouse, and around and down into Oak Bluffs harbor.
    At end of road (market on your left) take a left onto New York Ave.
    You are now in Oak Bluffs.
    You will pass marina on left, Gingerbread houses on right, stop sign w/ Circuit Ave on right, movie house on corner, (Circuit Ave is the main street of shops on OB) Keep going straight - pass Giordano's pizza and Richardsons ice cream, Carousel on your left, towards ocean and when you can't go any further take a right onto Seaview Ave/Edgartown Oak Bluffs Rd.
    This will take you past ocean on your left, and eventually Joseph Syliva State Beach on left and Sengekontacket Pond on right - keep going straight until you come to the "triangle" (where Edgartown-Oak Bluffs Road meets Vineyard Haven Road on your right, latter has a stop sign, you don't). Now you are on Upper Main St. You will pass on your left Stop and Shop market, Shiretown Meats, Liquor/cheese store on your right and keep going straight into Lower Main St and into Edgartown. you will cross a few streets (pass Courthouse, Alchemy restaurant, Movie theater) - you will see cross of N. Water St and your inne is down there on your left.

    This is a much prettier drive then taking the Vineyard Haven road to Edgartown and this might sound confusing but won't be when you do it.

    Also: parking - I don't think it will be so bad in Oct, not like in summer - but if you are having trouble:
    In Edgartown; you won't need to park at all, you can walk evrywhere from your Inne. In OB: street parking up near ferry, along marina near nancy's restaurant which is across from gingerbread houses, or on circuit ave (which leads to sweet life cafe, a slice of life, good dog goods and library)
    In VH: if you don't find something on the main street where th shops are (Zephrus, Moxie Cafe, Books store) just keep going past bank on left (great building) and I usually find something further up on the left. If not, you can circle around and take a right where you see a parking sign into the lot for supermarket, but that is usually full.

    Have a blast ! Take a deep breath on arrival and chill the MV way. Thank us all by telling us all about your trip and your favorites when you return.
    If you think of anything else, I'll check again over next few days. Have Fun !!

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    Good evening!

    I have a last minute MV question that I had meant to ask so many times but I think just got lost among the larger details:

    How is the star gazing on the island?

    Thank you!!
    :)

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    stars are clear on a good night, as in most places, and there is less light than in a city, but not as little as if in more remote areas -aside from the weather in general, it also depends on when the fog moves around that is often in Nantucket Sound - but usually Vh is not as foggy/ you will actuallly be able to see Falmouth (WoodsHole) from the island, esp on a clear day and you will see their lights at night.

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