10 Amazing Stops You Have To Make on Your Vermont Road Trip

The state of Vermont is undeniably charming, quaint, and filled with plenty of picturesque views. If you’re lucky enough to visit during autumn, you’ll be even more overwhelmed with its beauty! Vermont’s name comes from the French phrase “vert mont,” which means “green mountain.” Once you hit the road in Vermont, the name will really come to life. Speaking of hitting the road, Vermont, being such a small state, makes for a perfect road trip destination.

Last month, I had the pleasure of visiting Vermont for the first time. Accompanied by two of my closest friends, we did our own little weekend road trip. The natural beauty, mesmerizing landscapes, and stunning colors of autumn in Vermont blew us away. Each and every place we visited during our time there was captivating and left such an impression on us. With that being said, here are ten amazing stops that I would 100 percent recommend making part of your very own Vermont road trip.

Fun Fact: In 1968 Vermont outlawed billboards. While driving through the state you won’t see a single one! Legislators didn’t want advertisements distracting drivers from the beautiful scenery. . . and from the road of course! So while you’re road tripping, don’t forget to enjoy the view. Let’s get to our list of amazing stops:

Road Trip Stop #1: Stowe, Vermont

If you’re flying into Vermont and renting a car for your road trip like we did, chances are you will be landing in Burlington. Burlington is a city in the north, close to the border of New York, and is a great area to start in. From Burlington, we drove just under 45 minutes to reach Stowe. Stowe is well-known for its mountains, trails, and ski slopes.

We spent the afternoon exploring the town and really enjoyed it. We had lunch at The Whip Bar & Grill which has been around since 1833! The Whip is also a popular accommodation if you’re looking for a place to stay in Stowe. Check out their website here. Located right on Main Street, we took a lovely stroll afterward to work off our lunch and enjoyed the cute shops and charming town views.

If you want to really take in the landscape while visiting Stowe, check out Mount Mansfield. This is the highest mountain in Vermont with peaks over 4,000 ft above sea level. And if you’re visiting Vermont during the winter season then you will be in luck with amazing ski resorts.

Another fun thing about Stowe is the variety of breweries you can visit. Stowe is home to The Alchemist, Idletyme Brewing Co., and von Trapp Brewery.

Road Trip Stop #2: Cold Hollow Cider Mill

A 10-minute drive outside of Stowe will bring you to Cold Hollow Cider Mill. With over 350,000 visitors a year, this is a very popular tourist destination in Vermont, and for good reason. Cold Hollow Cider Mill is the largest maker of fresh cider in the Northeast, producing more than a million gallons a year!

This is a fantastic place to pick up some Vermont souvenirs and enjoy tons of locally made products. There was an overwhelming amount of choices of jams, jellies, spreads, maple syrups, and baked goods. They even have a cider tasting tank on the premise with some of the freshest apple cider I’ve ever tasted. You can also watch the cider production using age-old methods. And last but not least, Cold Hollow Cider Mill is famous for their apple cider donuts, which you’ll regret not trying! They’re served warm with just a mildly sweet taste and a perfectly soft texture. For more information on Cold Hollow Cider Mill check out their website here.

Road Trip Stop #3: Ben & Jerry’s Factory

Did you know that Ben & Jerry’s ice cream started in the state of Vermont? Here’s a funny story: 

Ben Cohen & Jerry Greenfield met in their 7th-grade gym class in Long Island, New York. They were apparently the two slowest kids in class so by default they ended up becoming best friends. After college, they had ideas of starting their own business and moved to Vermont where the competition wasn’t as crazy as NY. They initially wanted to open a bagel shop but the equipment was so expensive that they decided on ice cream instead.

Their first shop was in a small renovated gas station in Burlington, VT. It didn’t take long for people to take notice and Ben & Jerry’s became a cult hit in the state. Within a couple of years they expanded through the east coast and their fun, exotic flavors were becoming favorites among many. Now you can find Ben & Jerry’s in 35 countries!

And if you’re visiting Vermont, then the Ben & Jerry’s Factory should definitely be on your list. It’s only a 20-minute ride outside of Stowe and makes for a really fun road trip stop. Here, you can take a tour of the factory (given there isn’t a pandemic going on) and indulge in one of the many delicious Ben & Jerry’s flavors. Don’t forget to check out the “Flavor Graveyard” where they put old flavors to rest. To plan your trip to Ben & Jerry’s factory, check out their website here.

Road Trip Stop #4: Vermont Route 100

While on your road trip, chances are there will be a point in time where you find yourself on Vermont Route 100. This is Vermont’s most scenic drive! It runs through the center of the state, north to south, and there are plenty of picturesque places to stop along the way.

If and when you find yourself on Route 100, keep a lookout for spots on the road that you can stop off. The drive has many twists and turns so areas to stop off come up very quickly. But, if you happen to see an extra-large shoulder on the road, it’s totally worth it to pullover (ONLY WHEN IT’S EXTREMELY SAFE TO DO SO) and really take in the scenery. 

Road Trip Stop #5: Montpelier, Vermont

Montpelier isn’t just the capital of Vermont but it’s also the smallest state capital in the US. With that being said, even though it is small, it has so much to offer! The town of Montpelier is a perfect place to stroll around, take in the scenery, and stop off for a nice meal. There are plenty of outdoor activities to do from cross country skiing in the winter and hiking in the fall. There are also plenty of galleries and museums. Not to mention, the beautiful gold- dome State House is definitely worth checking out!

Road Trip Stop #6: Woodstock, Vermont

Woodstock is located in central Vermont and was named “the quintessential New England Village.” Walking around Woodstock feels like you’ve been placed on the film set of Gilmore Girls! This town is filled with beautiful local-owned shops, adorable cafes and restaurants, picturesque views, and stunning 19th-century buildings. It goes without saying that Woodstock is definitely one of those “must visit” places in Vermont!

Your day in Woodstock should start off with a delicious breakfast. Of all the cute cafes that line Central Street, I’d recommend either Mon Vert or Soulfully Good Cafe. They both use fresh, local ingredients and are passionate about their coffee. There’s plenty of cute shops to check out while visiting Woodstock. It’s worth stopping in Yankee Bookshop, which was opened in 1935 and is Vermont’s longest-running independent bookstore. Then there’s F.H Gillingham & Sons, which has tons of great quality local products such as maple syrup, cheese, macaroons, honey, and so much more. Lastly, Red Wagon Toy Co. is an adorable shop and a great place to buy gifts for any little ones in your life. You’ll be mesmerized by all of the charm Woodstock has to offer.

For a full guide on how to spend a perfect day in Woodstock check on my blog post here.

Road Trip Stop #7: Middle Bridge

Vermont is quite well-known for all of its covered bridges- to be more precise, there are over 100 of them! Some of them date back to the 1820s but most were constructed from the mid to late 19th century.

I would definitely recommend adding a covered bridge to your Vermont road trip itinerary and if you happen to stop in Woodstock then you’re in luck.

Just off of Central Street you will stumble upon Woodstock Middle Bridge. This is a beautiful, wooden covered bridge that will have you imagining that you’ve laid your eyes on a painting. A great feature of Middle Bridge is that there is also a path for pedestrians wanting to walk over and the views are stunning! This area can get a little congested between tourists (like myself) wanting to take photos and cars wanting to actually use the bridge for its intended purpose, but with a little patience, it was easy to have the place pretty much to ourselves.

Road Trip Stop #8: Billings Farm & Museum

The state of Vermont is also filled with farms. Extremely picturesque ones at that! Right outside of Woodstock is Billings Farm & Museum. This isn’t just a working farm but it’s also an extensive museum dedicated to scientific farming history. Located just a short 2-minute drive outside of town, you’ll experience the beautiful Vermont countryside here at Billings Farm.

Through their tours, they offer diverse, interactive programs that focus on rural life, traditions, and values dating back to the 19th century. If you’re interested in discovering more about Vermont’s rural history, this is a great place to start. If you’re not interested in taking a tour Billings Farm is still a beautiful place to see Vermont’s scenery, enjoy the autumn foliage and even spot a couple of cows.

Billings Farm is also connected to Marsh-Billings-Rockefeller National Historical Park, which is a national park that preserves the forest on site. There are beautiful walking trails, historical buildings that can be toured, and stunning views of Vermont’s natural beauty. For more information on Billings Farm & Museum check out their website here.

Road Trip Stop #9: Jenne Farm

Jenne Farm isn’t just the most photographed farm in Vermont, but it’s possibly the most photographed farm in the world! The story goes that about 50 years ago, Jenne Farm was discovered by a photography school in South Woodstock out taking photos. Eventually images from the farm started popping up in calendars, postcards and magazines. It even made it in Life magazine photo contests and eventually in a Budweiser commercial. Believe it or not, Jenne Farm is even in the movie Forrest Gump!

Located just about 20 minutes outside of Woodstock, this is a stop that should not be missed. Let me just tell you right now, it is beyond gorgeous! You’ll enter a dirt road that is technically two-way but you’ll wonder how two cars are meant to drive down it at the same time. I’d recommend parking a little ways from the farm and walking the rest of the way to take in the scenery. The rolling hills, beautiful valleys of green, and outstanding colors of the changing leaves will leave you absolutely breathless! It’s one of those places that the pictures don’t quite do it justice and you just have to see it for yourself in person.

Keep this in mind when visiting: Jenne Farm is a private residence so always be respectful when walking around and taking photos of the property. It obviously doesn’t cost anything to visit Jenne Farm, but there is a donation box on the premises.

Road Trip Stop #10: Quechee Gorge

About 15 minutes east of Woodstock is Quechee Gorge. This one we stumbled upon by mistake and it ended up being one of my favorite parts of the trip. We were seeking out a winery and my google maps led us to Quechee Gorge Village- a connection of different antique and souvenir shops, homemade fudge, a grocer with local products, and a little corner where wine is sold. (Not exactly the winery we had in mind) On the left-hand side of Quechee Gorge Village is an adorable Alpaca Farm and just over the bridge is “the” Quechee Gorge, a sight absolutely worth seeing! It’s one of those views that are completely untouched by mankind and have seemed to remain just as mother nature intended it to.

At Quechee Gorge, we also took notice of this map of Vermont. This gave me so much inspiration for my next Vermont road trip and maybe it can help you with yours too!

I hope you have found these Vermont road trip stops enjoyable to read about and I really hope they have inspired you in taking your own Vermont road trip one day. If you have any questions, comments, or suggestions, please feel free to leave them below. Thank you so much for reading and happy travels!