Spots to Visit Along Route 100 in Vermont

Autumn is my favorite season and I had the awesome opportunity to go on a beautiful fall foliage trip! If you love the fall as much as I do and want to go beyond the apple picking and pumpkin spice lattes then you NEED to go on a trip like this!

Our game plan was to drive from Long Island all the way up to Vermont on route 100 then drive back down to the Catskills area and then drive more down to Albany NY. This article will focus on the drive up to Vermont. The Catskills and Albany trip will be for the next articles šŸ™‚

So here are the places we stopped at along Route 100, I won’t talk much because the pictures will do the talking for me šŸ™‚

Just an FYI, Route 100 starts at Stamford, Vermont. So what we did to get there is put directions to Stamford, Vermont on our phone. We passed by Connecticut and Massachusetts.

I’ve also made a playlist of songs worthy enough for a road trip, enjoy šŸ™‚



On our way there we stopped at a diner to use the bathroom. Reason why I’m telling you about this is because we found a cool barn across from it! And if you need a food/bathroom stop, this place is here.
O’s Eatery American Diner in Chatham, NY

We spotted this old abandoned barn across the parkway from the diner. I don’t advise going here but this was just a fun little spot to take pictures at. There’s no real address though and it was a little scary!
Abandoned Barn in Ghent NY 


As we were driving along heading into Massachusetts, we started to see mountains! So we made a quick stop along Hancock Rd on route 43 to admire and take some photos šŸ™‚


This was our first stop when we got to Vermont! Completely spontaneous, it was just along route 100! It was a beautiful stream with a bridge to walk over it. We were breathless!
West Branch Deerfield River in Readsboro, Vermont


This stop was completely spontaneous as well! It’s a gorgeous lake! You could see the beautiful trees for miles.
Sadawga Lake in Whitingham, Vermont


If you want authentic, homemade cider donuts, pies, cider, Vermont maple syrup and everything in between then you HAVE to visit Cold Hollow Cider Mill! You can smell the cider goodness from outside the store! They have pretty much everything. They have sweets, drinks, clothes, and novelties. I bought a cider doughnut, vanilla pumpkin cookie, pumpkin pie, a cinnamon bun and a Vermont mug šŸ™‚ The sweets were DELICIOUS! It’s so worth going there. They even have seating outside, they have cute wooden seat swings!
Cold Hollow Cider Mill in Waterbury, Vermont

Just down the road and 4 minutes away there’s the Ben and Jerry’s Ice Cream Factory. Although I can’t tell you about the tour guide because we were late and missed the last tour of the day, it’s still a pretty cool spot to visit and get some ice cream. I got chocolate chip cookie dough ice cream on a waffle cone šŸ™‚
Ben and Jerry’s Ice Cream Factory in Waterbury, Vermont

For dinner, we went on Main Street in Waterbury. It seemed like an up and coming lively street with many restaurants and bars. Originally we wanted to go to The Reservoir but it was a long wait. So we went inside the Blackback Pub instead. It was a small intimate place and I felt right at home. I love places that make me feel like that! The service was great and the food was delicious as well. I decided to be a little adventurous so I ordered a Cool Sesame Peanut Noodle Bowl with chicken. It was medium spice and had veggies and tamari nuts. It was actually pretty good! It was different though because I never had cold noodles before.
Blackback Pub in Waterbury, Vermont (Dinner)

These were the places we visited along route 100 in Vermont. There’s so many other spots we could have checked out I’m sure but for that we need more time! I hope when you decide to take this trip you’ll follow along and add more to the list!

I’ll be writing up the Catskills and Albany trip in the next few articles as well as my fall foliage guide! So stay tuned!
Don’t forget to follow along my Roadtrip Spotify playlist šŸ™‚


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