Background: Our Fall Foliage Adventure
Ever since I was a kid, I’ve wanted to go to New England in the autumn to see its famously bright fall colors. One of my dearest friends lived in Boston and we convinced two of our other great friends to fly out and join us on an adventure across Massachusetts, Vermont, New Hampshire, and Maine to see some of the best fall foliage the country has to offer.
It’s always fun to make a list of goals for a trip, whether easy or far-fetched, silly or serious. Here were our goals for the trip:
- Meet random people!
- Hidden – NSFW 😂
- Eat lots of yummy local food!
- Hidden – NSFW 😂
- See lots of cute small towns!
- Admire fall foliage! (Obviously)
- Hidden – NSFW 😂
- Stand under a variety of covered bridges!
- Climb mountains, cross rivers, & hug trees!
- Meet politicians campaigning in New Hampshire! (We went in 2015)
- Reach great highs and strong buzzes!
Boston to Greenfield
We picked up our rental car – which was hilariously a tiny subcompact Mitsubishi – and the four of us left Boston early to drive west on Highway 2 toward Massachusetts’ scenic Mohawk Trail. An hour and a half drive took us to Greenfield, a small city on the eastern terminus of the Mohawk Trail. Just before we entered the city, we stopped at the French King Bridge to get an epic view of the Connecticut River and surrounding foliage (see top photo).
In Greenfield, we went to Poet’s Seat Tower, an observation tower built in 1912 that has a panoramic view of the city. It’s free and open to the public – just take two stairwells to the top. We had it to ourselves until a car pulled up and we witnessed what appeared to be a drug deal and/or a scandalous teacher-student relationship 😂

The Mohawk Trail
From Greenfield, we drove west on Highway 2. (Highway 2 between Greenfield and Williamstown is considered the Mohawk Trail.) Our first stop was the town of Shelburne Falls, a cute tiny town with a historic downtown and a famous Bridge of Flowers which is exactly what it sounds like 😉 You can walk on the floral bridge itself or another bridge next door to get a good view of it. From the southeast side of the bridge, we walked down Deerfield Avenue to a series of beautiful white water rapids on the Deerfield River.

We got back onto the Mohawk Trail – after six miles, we saw a stop we knew we had to make: a corn maze! The Hicks Family Corn Maze was only $6 and we were given a paper with some landmarks we needed to find in the maze so that added an extra element of fun.

Then it was back to the drive – once the road entered Mohawk Trail State Forest, we began to stop frequently to savor the epic views. We stopped at Eastern Summit Gift Shop just past the tiny town of Florida and were amused by a collection of “mystery gifts” they sold that were wrapped and labeled according to the ideal recipient (young girl, adult male, etc.). From this shop atop a hill, there was a stunning view of the surrounding fall foliage.

After five more miles, the road came to a dramatic bend and began to drop into a valley. Right on the bend, we saw a quaint-looking building that was a treat for our hungry eyes – the Golden Eagle Restaurant. The food was traditional American food and fairly average, but the view was quite scenic. We experienced some subtle racial prejudice from the staff 😡 – don’t listen if they tell you to use the outdoor port-a-potty.
Southern Vermont
We reached the end of the Mohawk Trail in Williamstown, turned right on Highway 7, and crossed into Vermont. Our first stop was The Apple Barn & Country Bake Shop just before the town of Bennington 10 miles past the border. Vermont is famous for maple syrup and our first stop in the state certainly lived up to this – they had maple flavored everything! I opted for some maple flavored froyo – mmm! Next, we stopped at Goodwill in Bennington as Halloween was coming up and I didn’t have a costume. They had the best costume selection I’ve ever seen and I walked out with a fabulous (life-changing) $5 tutu 😉
We continued north on Highway 7, following signs to take Highway 313 to Highway 7A to reach the town of Manchester (30 minutes north of Bennington). This quintessential New England town had a tall white church tower and great views of the surrounding mountain peaks. We were short on time, so we took a quick walk and then drove straight to Burlington via Highways 30, 22A, and 7 which interestingly took us through New York for a few minutes. As we drove through cute small town after cute small town, we noticed that New England has a TON of cemeteries! There were probably more dead people than live people in a lot of the towns. 😲

A Night Out in Burlington
We checked into our hotel for the night – the Colchester/Burlington Motel 6. Our goal for the trip was to spend as little as possible on lodging and some research found that New England’s hotels are cheaper than AirBnbs and we were able to secure the cheapest 2-bed room each place we went 😉

Upon researching the best eats in town, we decided upon Kountry Kart Deli, a sandwich shop in Downtown Burlington. My friend called to ask if they had any tables available and got laughed at since (as we later found out) it’s a counter-serve deli without any tables. The sandwiches were large, delicious, and all under $10 – a great find!
We then walked a block over to Club Metronome, one of the only clubs in this small city. Shockingly, there was a line and it was bitterly cold so that wasn’t fun. But once we got inside, we went up to the 2nd level and danced for a bit until we got tired and went home for a good night’s rest.

Click here to go on to the Fall Foliage Day 2 blog as we fend off dog attacks and explore some of Vermont’s delightful towns.
About the Guest Author: Travel doesn’t have to be expensive, time-consuming, or difficult! No matter your constraints, you can get away to somewhere near or far and discover something magical.
I love hiking amidst beautiful scenery and exploring new cities and areas. My site aims to provide you with tips on the best cheap and free things to do and see and affordable places to eat and drink in U.S. cities and national parks, as well as few international destinations. While many tourist spots are amazing and well worth your time, I always include a variety of off-the-radar places that are popular among locals to ensure that you experience a place as someone who lives there does.
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