GabiStephan, your title is cute...that's why I clicked on it. However the title doesn't mention where you are going. If you don't get enough responses, try re-posting a new similar question mentioning where you are going. (E.G. A German Couple Wants To Become Leaf-Peepers in New England)

Sorry I can't answer your question as I haven't traveled much to your destination! I went to a wedding in a cute little town in Vermont... I seem to have forgotten the name of the town...I'm not much help! But Vermont is pretty. Some interesting artists live in Vermont.

I remembered the name of the little town in Vermont where we stayed to attend a wedding...Brandon, Vermont. American folk artist Warren Kimble lives and works in Brandon, Vermont. You can google "Brandon, Vermont" for more info.

Enjoy your trip.

Not sure about the 1 night in Hadley. The Big E is great and would be a fun experience but you're talking about going from Western MA (Hadley) to Eastern MA (Gloucester). Certainly you can do that in one day but you wouldn't see much of the fair or Cape Ann.

The Hotel Marlowe is a good choice. I love it and it's an easy walk to the Museum of Science. Just avoid the breakfast buffet in the hotel restaurant. I think it's called Bambara.

Rte. 100 and 100a going up the spine of Vermont might be one of the best roads for color and old Vermont villages.

Your Boston part of the trip should be lovely this time of year, and the city is so walkable you won't have a problem seeing all the sites. One thing to add would be dinner at Durgin Park at Quincy Market. A local legend. And Union Oyster House is one of the oldest restaurants in the US and it's just across the street from the Quincy Market as well.

In New Hampshire, you might add Meredith to your iterary. Meredith is a lovely town right ON Lake Winepausauke and the leaf peeping there is breathtaking. There's also a lovely inn right there as well. A good restaurant in the area is a local legend "Harts Turkey Farm". You also might enjoy some of the outlet shopping in the area, just ask any of the locals.

Olde Man of the Mountain had his face fall off not long ago, but the mountain is still there and a bit further up is Indian Head and The Flume, also might be worth a stop.

The local "doll factory" called Annalee is also really well known all over New England. I can find Annalee here in New York sometimes too, and would be a nice reminder of your trip to take home.
www.annalee.com.

You are in for such a GREAT trip.

Hi GabiStephan,

Looks like you have a great trip ahead of you!

I will echo the suggestion that you may want to skip The Big E, unless you've already booked your accommodation in Hadley. It just isn't ideal to drive out to western Massachusetts and then back to the Gloucester area. It will be much easier to see western Massachusetts on your journey from Vermont to Connecticut, although I know you wanted to attend the fair.

If possible, I would recommend using your 4th day exploring the towns north of Boston -- Salem is great for history, then continue along Route 127 through Manchester-by-the-Sea and Gloucester. Follow the loop around Cape Ann through Rockport, then take Route 133 through Essex and Ipswich. From there, follow Route 1A to Newburyport. These are some of the most historic and well-preserved towns in America. I would probably recommend spending your fourth night in Newburyport.

On your way towards Ogunquit, either take I-95 North (faster) or 1A North (to see the beach towns and mansions) into New Hampshire. YOU MUST STOP in Portsmouth -- this is one of the most well-preserved colonial port cities in New England -- like Newport, but much less well-known. Take Route 1B through Newcastle and then walk around downtown Portsmouth, including the Strawberry Banke Museum. You won't regret it!

The Kittery Outlets are across the bridge from Portsmouth in Maine (although the cheapest outlet shopping will be in North Conway -- New Hampshire has no sales tax). Make sure to stop at Cape Neddick to see the Nubble Lighthouse. After Ogunquit, you might consider passing through Kennebunkport and then taking the highway up to Cape Elizabeth to see the Portland Head Lighthouse. Freeport is only worth stopping at if you want to see the L.L. Bean Store, and skip The Desert of Maine at all costs - it's a ripoff and not very interesting, in my opinion.

The Boothbay Harbor area will be nice to explore. I strongly recommend driving along Route 1 up to Wiscasset and Damariscotta, then down Route 130 to Pemaquid Point. There's a lighthouse and beautiful rock formations along the coast (costs $2 to park, but it's worth it). If you can manage it, I HIGHLY RECOMMEND continuing north along Route 1 to Camden. Camden is very charming, but the real treat is the Camden Hills State Park just north of town. You can pay a few dollars to drive up Mt. Battie for one of the most spectacular views in all of New England.

To get to Conway, you will probably want to retrace your steps back to the Portland area and then follow Route 302 West. For the most part, you will be a little early for the best autumn colors on your trip (you'll see lots of green when you arrive), but once you get to the White Mountains you will be amazed! Must-do scenic drives: Kancamagus Highway, I-93 North through Franconia Notch State Park (stop at The Flume Gorge), Route 302 through Crawford Notch State Park, Bear Notch Rd., and the Mt. Washington Auto Road off Route 16 (if the weather is clear -- most incredible views in all of New England!) Also look into Weeks State Park in Lancaster -- more wonderful views there!

Conway can be busy during leaf-peeping season, but one good tip is to bypass Main St. (Route 16 / 302) by using West Side Rd., which runs parallel and is much quieter. This road also leads you to Cathedral Ledge and Echo Lake State Park, which is a wonderful place to visit in the fall.

Squam Lake ("Golden Pond") is a lovely area and you must visit the quaint village of Center Sandwich nearby. Consider driving west from Center Sandwich along Route 113 about 5-6 miles and then doing the short and easy hike up Rattlesnake Mtn. for a breathtaking view of Squam Lake. The locals can help you find the trailhead parking if you miss it (it's just big dirt parking lots on either side of the road). You can continue on to Holderness and Meredith if you wish; another nice place is the Castle in the Clouds in Moultborough, but you don't want to take too much time away from seeing the White Mountains!

From Conway to Rochester, VT, there are essentially two routes you can take (a northern and a southern) which will involve about 3.5 hours of driving. Neither one is very straighforward. If you're trying to save time, then I would take the southern route which would take you through Sandwich and the Squam Lake area, then Meredith; from there you would take Route 104 W -> Route 4 W -> I-89 N -> Route 107 W -> Route 100 N.

However, if you manage to see Squam Lake before day 10, then the more scenic route to Rochester is probably the northern one. From Conway you would take Route 302 W -> I-93 N -> Route 2 W -> EITHER I-89 S -> Route 107 W -> Route 100 N OR I-89 N -> Route 100 S. You will cover a lot of beautiful country.

It's a little strange that you chose to stay in two towns in Vermont which aren't that far from each other! But that's all right -- it just means a little more driving to get around the state. If you head up to Burlington then you definitely want to drive Route 100 (perhaps up to Stowe), and then maybe Route 7 on the way back (stop at Mt. Philo in Charlotte for another classic New England view). The Shelburne Museum is also very interesting.

When it comes to exploring Vermont, it's difficult to choose "scenic drives" because they're all gorgeous! Don't be afraid to get a little lost. However, it's a good idea to have state atlases with you (the Delorme Map company makes great ones -- they're usually available at supermarkets, and there's also the Delorme Store in Yarmouth, Maine). They cost about $20 apiece but they are extremely useful for road trips.

Woodstock is a beautiful town. Make a stop at nearby Quechee Gorge as well. Cross back over into New Hampshire to see the Cornish-Windsor covered bridge and the 2 or 3 other covered bridges in the town of Cornish (also home to the Augustus Saint-Gaudens Museum).

From Tafstville, I would probably recommend making your way over to Manchester, Vermont (doesn't really matter which route you take), and then driving south along Route 7A towards Bennington. Make a stop at the Equinox Skyline Drive for more incredible views. In Bennington you can visit the Bennington Battle Monument if you'd like. Continue on Route 7 South to Williamstown, Massachusetts; then follow Route 2 East towards North Adams (maybe stop at Mt. Greylock?). I would probably consider spending your night in the North Adams area.

The next day, continue on Route 2 East until you reach Route 5 in Greenfield, which you can follow south to historic Deerfield (also home to Yankee Candle). Continue on to Old Sturbridge Village and then Thompson (or visit Old Sturbridge Village the next day if you're low on time).

2 days might be a bit much for the Thompson area, but I'm sure you'll want to wind down and take a break from driving at this point! Once you head down to Mystic, make sure to take the scenic Route 169 S -> 14A E -> 49 S. This will be a lovely drive in October. Actually, if you want to break up the driving a little bit then you might consider spending a night in Mystic instead of 2 nights in Thompson (if this is still possible).

Newport is a fantastic place. You'll have plenty to do and see. I also recommend seeing adjacent Jamestown, especially down at Beavertail State Park.

Sorry for the information overload, but I hope that I've been helpful! Have a great trip!

If you are in Brandon, VT, be sure to go to "Cafe Provence", right on Rte 7, for lunch or dinner. Some people are afraid of the cost because of the name, but don't be.

We were there recently (again), and my delicious, chef-prepared lunch cost me all of $7.00. It was somewhat unusual: a pasta dish with goat cheese and other delicious ingredients, with a small salad and some nice toasted bread pieces. I saved some to take home, too.

They offer all kinds of wonderful salads and other things, plus some desserts that will amaze you, for reasonable prices.

What TerrMys said! Center Sandwich is delightful. It might be a little crowded during Columbus Day weekend because the Sandwich Agricultural Fair is held during that time. If you have the DeLorme Atlas you can find the seasonal notch road. The road doesn't have great views but there's a small waterfall located a short walk from the road. If you are short on time, skip it. Also you might try to find the Sandwich Creamery if you like ice cream. It's a little adventure to find it. Twice we have seen black bears on or near the road in the Center Sandwich area.
Also agree with recommendations for Maine and Portsmouth and visiting Brandon VT. If you get to Woodstock VT, Simon Pierce is a must see in Quechee even if you don't eat in the restaurant, the building is fascinating, They generate their own hydro-electric power.
We love Wiscasset. Pemaquid is a great recommendation to see the lighthouse. We also like to drive out to Harpswell. There's a small restaurant on the point, Dolphin Marina. South Harpswell is very rural yet only 14 miles from the college town of Brunswick. So many beautiful places!
Just north of Brandon is the town of Bristol. If you go thru Bristol you can take the rt thru Lincoln Gap over to Rt 100. Near the beginning you should get a glimpse of a beautiful, rocky river. In the fall you might just drive right by but we visited in the summer, saw a lot of cars and discovered this was a popular swimming spot. The river is shallow in one section so you can walk across (very rocky, though) but upstream there is some ledges and a small waterfall with a deep pool. Kids were jumping off the ledges into the pool. One of the rites de passage for a country kid. You won't see the waterfall unless you park the car and walk a little. It's very close to the road so you should see some well worn paths. We picnicked on the ledges and watched the kids on a beautiful summer day.
Whenever people post an itinerary that is very busy with driving I worry that they will miss the small gems by the side of the road. I live here and I still enjoy the small surprises and beauty.

WOW WOW WOW I am so overwhelmed by your detailed responses.
DH and I are going to print this out and try to follow all of your suggestions. I cant say enough THANK YOU

I would skip Sturbridge Village and do my last 4 nites or so in Newport. From there, it is only about 45 minute drive to Mystic so this can easily be done on a day trip.

I would echo EmilyC.

I agree you'd be better off not driving all the way out to Hadley on your way to Gloucester -- its too far west.

Better to fit it in on your way from VT to CT. Its only about 40 minutes from the main Yankee Candle store in South Deerfield, on your way to Sturbridge Village. Amherst and Northampton are nice places to stop and look around in that area, too. But check when the Big E closes down -- it might be too late.

Instead of the Big E, you might enjoy the Paradise City Arts Festival in Northampton. It doesn't have the rides and junk food, but it is a pretty nice festival with art and music.

I agree with adding Stowe, VT, to your itinerary. It is a lovely town.

If you'd like to check out some picturesque shops, in Vermont be sure to go to Dan and Whit's in Norwich, the Warren Country Store in Warren (of course), and Gillingham's in Woodstock. For giggles go to the Unicorn in Woodstock, too. When you're in Burlington, be sure to see Church Street, and also go down to the waterfront. Have lunch at A Single Pebble -- their mock eel is their signature dish and an absolute must!

I'm not sure of the timing, but there is a fantastic place to see the snow geese when they migrate -- at Dead Creek not far from Middlebury. This is a phenomenal sight and worth just about anything to see if the timing is right.

New England is beautiful any time of year, but especially so in the Fall. It's tempting to try to see everything, but if you so slower and allow yourself to take back roads and to get lost, you'll not regret it. Plus you won't be exhausted when you're done! Have a wonderful trip.

Not sure if the timing will work out right, but another alternative to the Big E would be the Cumberland Fair (Cumberland, Maine), which is Sep 27 - Oct 3. You could hit that on your drive up from Ogunquit to Boothbay Harbor. It's not as big as the Big E, but it will give you a good experience of a traditional agricultural fair.

www.cumberlandfair.com is the link.

And I agree with PP on skipping the Desert of Maine!!

Old Sturbridge Village is a delight -- pure and simple. When you enter, it is as if you have stepped back in time to the early to mid-1800's in the U.S.

We used to have a family membership so we could visit 3-4 times a year, because they simulate an actual village of the period, and are always doing what people in that era would do at that season of the year.

However, it is also a place that deserves a full day to truly appreciate. If that is not a chunk of time that you have, I agree that it might be bypassed in favor of some other places.

I have toured this entire area many times. My sister lives in Auburn, Maine. It is the most beautiful place on earth in the fall. I try to go every year. I agree with the response Terrmys. I would highly recommend going to the VErmont Country Store in Weston. We just happened up on it and just couldn't believe it was in this little bitty town. The drive from Woodstock to Weston is breathtaking first 2 weeks of Oct. The apple/arts fairs in Woodstock and Weston are fun over Columbus Day weekend. I highly recommend the Woodstock Inn--must make reservations way ahead. I also love Camden, ME. I would make time to go up there. Have a great time!

My impression of the Vermont Country Store from a trip report of a few years ago:

On our way to Manchester we stopped in Weston. The town green looks nice, but would look better if the maples still had their leaves. We were about 2 weeks late for the high color season. The famous country store is now predominantly a tourist attraption [sic]. It used to be a country store with some local tourist items, now it is a tourist items outlet with some country store counters. There were no cars in the street of the town, and we discovered that the store has a large parking lot in the back for all the cars and tour buses.