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Boston and New England mid-October itinerary help

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Boston and New England mid-October itinerary help

Old Aug 17th, 2019, 03:45 PM
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Boston and New England mid-October itinerary help

Hello everyone! My wife and I are going to Boston for Columbus Day weekend, arriving Friday afternoon, Oct.11th and departing Monday, Oct. 14th in late evening. We're interested in food (seafood!!), history, shopping, culture, sight-seeing, and pretty wide open in terms of interests. NOT interested in doing group tours or Hop-On-Hop-Off buses. We like to walk and use public transit. Also interested in seeing some fall colors and a possible day or overnight trip somewhere outside the city. We like to rent a car or go by train when venturing outside the city. We have been to Boston previously, and have done the major attractions like Freedom Trail, Fenway Park, Museum of Fine Arts, Seaport District, Harvard, etc., so doing those things again is not a priority.

We are debating on whether to spend the entire weekend in Boston (I'm sure we'd find plenty to do), or take some of the weekend to get outside of the city and see some fall foliage or whatever else. We were interested in maybe taking the train to Portland or Providence and exploring those cities (likely an overnight trip), fall foliage in Vermont/New Hampshire, or maybe a day excursion to Salem or Provincetown. We are working on a medium range budget.

If anyone had any ideas for an itinerary or suggestions and tips on an ideal weekend itinerary, things to do, and places to visit and stay without feeling like we're cramming too much in, I'd greatly appreciate the insight. Obviously we're not going to see everything we want to see, but we'd love to maximize the time we do have. Cheers!
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Old Aug 18th, 2019, 12:17 AM
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I should add that a couple of proposed itinerary we have considered is:

ITINERARY A
Day 1 - Fly into Boston mid-afternoon and enjoy the evening in the city somewhere
Day 2 - Rent car and take road trip to see fall foliage (likely Vermont and/or NH and end our driving day in Portland, Maine). Figured this would be a full day of driving and sight-seeing
Day 3 - Spend day exploring Portland and surrounding area; drive back to Boston in evening
Day 4 - Spend day in Boston and then to Logan Airport in evening (flight leaves at 8:40pm) to fly home

ITINERARY B
Day 1 - Fly into Boston mid-afternoon and evening in Boston
Day 2 - Boston
Day 3 - Ferry to Provincetown and spend day
Day 4 - Boston and fly home in evening

Itinerary A I feel gives us more places to see, the epic fall foliage, and a little taste of everything, but it feels harried. Itinerary B seems more relaxed and less harried, but no Portland (which I was interested in visiting) and no fall foliage.

Last edited by jeverett; Aug 18th, 2019 at 12:24 AM.
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Old Aug 18th, 2019, 02:14 AM
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I'll vote for Itinerary A. Your route would depend on what historical thing you would like to see: Canterbury Shaker village north of Concord NH, Hay Estate at the Fells (heading from NH toward VT), Strawbery Banke in Portsmouth NH, Kearsarge Indian Museum in Warner, NH (there's also a telephone museum but Warner has a Fall Foliage Festival so check museum hours during that weekend), etc. I would even nominate Lowell MA mills.
Keep in mind north/south interstates are going to be clogged with traffic. If you overnight in Boston, get a very early start Saturday morning if you are headed north. I saw heavy northbound traffic on I95 (Boston to Maine) around 9am one recent Saturday. Have a good map so you can find alternate routes. There will also be heavy traffic Friday since it will be weekenders plus commuters. One possible alternative would be to take a bus from Boston (South Station or Logan) to NH or ME and rent a car there. I use Concord Coach for NH to Boston/Logan. They are always on time. Train to Portland would also be a good idea. I would avoid the White Mountains area of NH.
Strangely enough, I89 from Concord NH to VT is very scenic. I think I93 to I293 to I93 is scenic once you get as far north as Manchester NH (I like the I293 option because it goes along the Merrimack River and you can see the old mills on the east side).

If you haven't done a food tour of Boston yet, that would be fun. I haven't done a recent one of Portland ME so can't recommend. I am a big fan of farmers markets with Norwich VT being one of my favorites. I haven't been to the one in Portsmouth recently. Norwich is very festive with music and several prepared food booths. You could also check out wineries, distilleries and hard cider tastings around the region to help you decide which direction.

With just a weekend and your interest in food, I think Portland ME with a visit to Portsmouth NH would be best. Columbus Day weekend is generally the last weekend some of Maine's lobster shacks (a true shack with picnic tables outdoors) are open. There is always lobster in Maine it just depends on the venue you prefer. At this point in time, you are probably going to have a limited choice for lodging in foliage areas including Portland.
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Old Aug 18th, 2019, 05:37 AM
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Originally Posted by dfrostnh View Post
I'll vote for Itinerary A. Your route would depend on what historical thing you would like to see: Canterbury Shaker village north of Concord NH, Hay Estate at the Fells (heading from NH toward VT), Strawbery Banke in Portsmouth NH, Kearsarge Indian Museum in Warner, NH (there's also a telephone museum but Warner has a Fall Foliage Festival so check museum hours during that weekend), etc. I would even nominate Lowell MA mills.
Keep in mind north/south interstates are going to be clogged with traffic. If you overnight in Boston, get a very early start Saturday morning if you are headed north. I saw heavy northbound traffic on I95 (Boston to Maine) around 9am one recent Saturday. Have a good map so you can find alternate routes. There will also be heavy traffic Friday since it will be weekenders plus commuters. One possible alternative would be to take a bus from Boston (South Station or Logan) to NH or ME and rent a car there. I use Concord Coach for NH to Boston/Logan. They are always on time. Train to Portland would also be a good idea. I would avoid the White Mountains area of NH.
Strangely enough, I89 from Concord NH to VT is very scenic. I think I93 to I293 to I93 is scenic once you get as far north as Manchester NH (I like the I293 option because it goes along the Merrimack River and you can see the old mills on the east side).

If you haven't done a food tour of Boston yet, that would be fun. I haven't done a recent one of Portland ME so can't recommend. I am a big fan of farmers markets with Norwich VT being one of my favorites. I haven't been to the one in Portsmouth recently. Norwich is very festive with music and several prepared food booths. You could also check out wineries, distilleries and hard cider tastings around the region to help you decide which direction.

With just a weekend and your interest in food, I think Portland ME with a visit to Portsmouth NH would be best. Columbus Day weekend is generally the last weekend some of Maine's lobster shacks (a true shack with picnic tables outdoors) are open. There is always lobster in Maine it just depends on the venue you prefer. At this point in time, you are probably going to have a limited choice for lodging in foliage areas including Portland.
Thanks for the great info and the warning on the traffic. Why do you suggest that we avoid the White Mountains area? That was one area we were interested in, and maybe visiting some farmers markets and cider mills (cider donuts!!) Along the way. I'll give the farmers market in Norwich a look. We were also interested in Montpelier and that area. It's going to be difficult to narrow our focus with so many great options.

​​​​I'm just trying to think what all we could fit in a single day going leaf peeping in Vermont and New Hampshire. It sounds like traffic could slow us down and force us to narrow our focus to just one specific area of one of those states.

As for food tour in Boston, we are definitely doing one. I know Airbnb offers a couple of foodie tours that look promising. Any suggestions for a good one?

Last edited by jeverett; Aug 18th, 2019 at 05:42 AM.
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Old Aug 18th, 2019, 06:07 AM
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We enjoyed Bites of Boston Food Tour South End (not to be confused with South Boston) last fall. This was a part of Boston we hadn't really visited before. Several years ago we did Michelle Topor's North End which would probably give you more old Boston history and Italian focus.

If you drive straight up I93 it goes right through the White Mountains. Last Fall we did a brief visit to The Flume visitors center which was better than I expected. I'm not a big fan of the mountains since some areas feel desolate to me and I prefer the more southerly E/W route thru Sandwich and Tamworth over the Kancamagus Highway. Columbus Day weekend it's going to be very congested. Even my favorite route will be congested as it begins at exit 23 and goes thru Meredith. We came home from Maine that way the Friday after 4th of July and it was crawling until we got past Meredith's downtown intersection. It's beautiful because it's right on Lake Winnipesaukee. North Conway's view of Mt. Washington from Main Street is wonderful. You might do a day trip from Portland to North Conway. I don't know how congested that route will be. A friend who lives between two I93 exits says she can always tell when I93 is bad because the state highway detour starts to get a lot of traffic. You would have to be careful about you're traveling hours. Monday is kind of a non-holiday and many schools are in session so if you travel back to Boston, the traffic is going to be heavy on Sunday and also on Monday.

Montpelier does have a nice farmers market and if you're lucky, a local is going to respond to your post. You'll find cider donuts at several
orchards. Should you decide to go to either Norwich or Montpelier, you will probably take I93 to I89. You could do a slight detour to Gould Hill Orchard which has a nice view toward distant mountains and their own hard cider. Check hours for tastings. They have cider donuts too. You've just detoured off Rt 103. Return to Rt 103 keep heading west to Warner. (keep in mind the Foliage Festival). Probably best to get on I89 and then exit 10 to get to Winslow State Park. Very nice view from the top picnic area. It's not as dramatic as Mt. Washington but nice. Return to I89 for continued trip to Vermont.
Montpelier to Portland ME is less than 4 hours and two choices of routes go thru the mountains so it's possible even on a weekend. I'm going to guess that the northern route will have less traffic.
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Old Aug 18th, 2019, 12:24 PM
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Leaf peeping is amazing but entails traffic and rooms that are booked very far in advance. Family members always booked a hotel room a year ahead. Get off on less traveled roads if you go; it is breathtaking.
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Old Aug 18th, 2019, 02:03 PM
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dfrostnh -

After reading your ideas and suggested routes, as well as heeding your warnings on the snarled congestion we are bound to face, I had some questions:

1) Would it be feasible to do leaf peeping in Vermont and/or New Hampshire as a day trip from Boston? Say we left Boston EARLY on Saturday and then returned to Boston that night, how much do you think we could realistically see in a day, and where would you suggest we go to get the most "bang for our buck" in a single day? That would take care of the accommodation part, as we have already booked our hotel in Boston for the weekend. We felt it would be wise to book now and then cancel later if need be.

2) Do you think if we did the route in "reverse" - driving from Boston to Conway, NH and then headed east to west through the White Mountains toward Vermont if that would make a difference in terms of avoiding congestion? Or does it really matter which direction you go?

3) Do you have any suggestions on places for cider and donuts in New Hampshire?

I appreciate your in-depth and thoughtful responses. They've been invaluable in helping us start putting some plans in place. Thanks!
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Old Aug 18th, 2019, 02:06 PM
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Originally Posted by HappyTrvlr View Post
Leaf peeping is amazing but entails traffic and rooms that are booked very far in advance. Family members always booked a hotel room a year ahead. Get off on less traveled roads if you go; it is breathtaking.
Thanks so much for your reply. I suppose the same question I asked rfrostnh I'm asking you as well. Do you think leaf peeping as a day trip from Boston is feasible? And do you have any suggested routes or roads that are "less traveled" that you are familiar with?
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Old Aug 18th, 2019, 05:18 PM
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*UPDATE*

We have finalized our itinerary and booked everything. Thanks for your help in helping us plan this. rfrostnh, we decided setting out for our leaf peeping road trip from Portland would be the best way to go to avoid the scourges of Friday evening and Saturday traffic coming out of Boston per your suggestion. So here's what we're doing:

DAY 1 - Arrive Logan Internat'l Airport in Boston at 3:15pm. Going to North Station and catching 5:00 Downeaster Amtrak to Portland. Arrive Portland 7:30 and picking up rental car before checking in at hotel. This should give us the evening to enjoy a nice dinner in Portland and maybe do a late night crawl up to Freeport to the LL Bean flagship store.

DAY 2 - Spend day in Portland and surrounding area, visiting lighthouses, or just doing whatever. Definitely open to any suggestions. I think we definitely want to go to Portland Head Lighthouse and get a lobster roll at Bite Into Maine, and then spend some time in the old port area of Portland

DAY 3 - Head out from Portland early on route TBD, tentatively thinking Highway 302 towards Conway, NH. I did want to stop at Peter Limmer & Sons store in Intervale and get fitted for some custom made boots. After that, it's wherever's clever and presumably we'll head through the White Mountains then head south towards Lake Winnipesaukee. Will definitely give stopping in Meredith and that Gould Hill Orchard you recommended if time permits. Then we'll end our day by driving into Boston, dropping our rental car, catching a late dinner somewhere, and staying there.

DAY 4 - Spend day in Boston. Definitely interested in a food tour. The wife is more interested in shopping on Newberry Street. Either way, our flight doesn't leave until 8:40pm, which gives us virtually the entire day in Boston to do as we please before heading to the airport in the evening.

I think this itinerary gives us a little bit of everything without us feeling like we're foregoing something we really want to do. Sort of a New England autumn sampler. Thanks again for your help, and I'm open to any further suggestions you may have that fit into this itinerary.
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Old Aug 19th, 2019, 12:52 AM
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LOL, there's no best bang for the buck. There's lots of choices and I bet you'll see some great color.
The reason why I prefer the southern route from east to west slightly below the mountains is that there are small towns like Tamworth and Center Sandwich. Tamworth has a new distillery which is beautiful to see even if you don't want to do a tasting. The Remick museum is also there but we have only explored the grounds on a bird watching hike, not gone into the museum. But the Sandwich Fair is Oct 12-14 so there will be some traffic. It's a small agricultural fair. Better check on Peter Limmer since they are closed major holidays which might include that weekend. A view of Tamworth https://visittamworthnh.com/
Lots of places for cider donuts and maybe more convenient than trying to get over to Gould Hill https://www.google.com/search?rlz=1C...E,lf:1,lf_ui:9

If you take the Tamworth to Sandwich to Moultonborough route you'll be going right by Moulton Farm. Meredith also has Hermit Woods Winery if you want to do a wine tasting. But the intersection causes a lot of traffic back up on this route might not be a good idea after all.

Each day of the weekend is going to have heavy southbound traffic at the end of the day. I93 gets backed up because of the toll booth in Hooksett plus I89 feeding into I93 just south of Concord. If you plan on going to Gould Hill because of donuts and hard cider tasting you can get off I93 at exit 17 and follow google map suggestion to Gould Hill. From there you could take Rt 103 west to Concord (you'll go by Concord Hospital) then follow directions to take Rt 3A south. It parallels I93 along the Merrimack River and you can get on I93 in Manchester which puts you south of the toll booth. The bus to Boston takes 3A if traffic is really bad on I93.

Have fun!
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Old Aug 19th, 2019, 05:26 AM
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Columbus Day weekend is usually a little late for foliage where I live in north central VT and color may also be past peak in parts of NH.
This map shows when foliage is likely to be good in different areas of New England
https://newengland.com/seasons/fall/...l-foliage-map/

If you search you can probably find a site that would give you up-to-date foliage reports when you are actually here. I would try to be flexible.
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