Travel Guide: Fall in Bennington, Vermont

travel guide bennington vermont

While I grew up in upstate New York, I probably spent 25% of my awake hours one state over in Bennington, Vermont. To be fair, I lived right near the VT/NY border, so heading on over to Vermont was only a 15 or 20-minute drive. Bennington is where I worked (I worked in a deli during summers and winter breaks from college and my first real marketing job out of college was in Bennington), where we went to the movies, and where we went shopping.

Vermont is beautiful during the fall. Since I grew up here, the fall in Vermont wasn’t anything new or amazing to me. It wasn’t until I moved away for college that I realized people from all over the U.S. were dying to get to Vermont for the fall or winter.

So if you’re looking to travel to Vermont this fall to do all the fall things (leaf peeping, beer tasting, and pumpkin picking), Bennington is a great option. I even posted about a weekend in Bennington a few years back on my blog (read that post here). Here are my suggestions of where to eat, shop, and stay in Bennington, Vermont.

Shopping in Bennington, Vermont

The Apple Barn

I’ve been going to The Apple Barn for as long as I can remember. I remember going with my family as a child, and now I go every year with my husband when we visit my family in upstate New York. The store has only gotten bigger (and busier) over the years.

Hands down the best thing The Apple Barn offers is their apple cider donuts. I’ve tried quite a few variations, and no store has ever made them as good as here. They have pre-boxed ones and mini versions, but I suggest getting them fresh at the counter – by the dozen and with cinnamon sugar on top.

If apple cider donuts aren’t your thing, there’s plenty of other baked goods (pies, muffins, strudels, and more), fresh Vermont cheese, maple soft serve ice cream, apple cider slushies, and more. I always pick up a jug of maple syrup to bring back to NJ. Over the years, my taste buds have changed and I much prefer real maple syrup over the store-bought kind. I’m spoiled.

Outside of the store, there are pumpkins and gourds to pick, as well as tons of photo opps (just take a look at their tagged photos on Instagram). They have a nice seating area and bathrooms, too, so you aren’t rushed out after you’ve bought your donuts or apples. They usually have a corn maze open

This place can get very busy – buses make stops every weekend during the fall season, so it’s best to go at a non-peak hour (right when they open or near when they are closing).

apple barn country and bake shop

pumpkins at the apple barn

apple barn bennington vt

Hawkins House

Hawkins House is a local jewelry store with a Vermont flair. They offer hand-crafted jewelry, pottery, blown glass, wooden ware, clothing, handbags, and accessories. The jewelry is definitely not everyone’s styles – they have plenty of simple sterling silver items, but some of the offerings are a little too funky/granola for my taste. Hawkins House is where my friend Amber got me my favorite claddagh ring as a birthday present. I wore that for years until I lost it one night in college. Still upset about that, to be honest.

Bennington Potters

This store features collections of stoneware pottery, all made in Vermont. There are actually two locations – the one in Bennington is called Bennington Potters Yard (the other is in Burlington Vermont). This store is over 5,400 square feet of retail space, and all the pottery is nicely displayed among  furniture, rugs, wall art and all kinds of decorative accessories. You can also take a tour where the potters themselves show (and tell) you how the pottery is made, from forming to finishing, to seeing glazing machines in production.

The Antique Center at Camelot Village

Camelot Village is Vermont’s largest antique center. There are over 145 dealers with antiques displayed in over 13,500 square feet of restored rustic barns. I’m not an antique-r (is that even a word?), but I do enjoy looking at all the items they have – old coins, art, jewelry, collectibles, and furniture.

Things to Do in Bennington, Vermont

Get a Taste of History

Many of the famous landmarks or tourist attractions in Bennington revolve around its history (the town is known in particular for the Battle of Bennington, which took place during the Revolutionary War). Here are a few notable ones:

  • Old First Congregational Church – This church borders the Old Bennington Cemetery, where poet Robert Frost is buried, making it a destination for tourists to visit his grave. It’s also just a really beautiful church, and the area is particularly beautiful during the fall as the leaves are changing.
  • Bennington Museum –  The Bennington Museum is home to the largest collection of Grandma Moses paintings in the world, and also has galleries of military history and contemporary and outsider art.
  • The Bennington Battle Monument – This is not only Vermont’s most popular historical site, but it’s also the tallest human-made structure in the state. The monument commemorates the Battle of Bennington during the American Revolutionary War. The monument also features an observation deck with views of three states (if you’re not afraid of heights, of course), and a small gift shop.

tourist bennington vermont

Visit a Covered Bridge

Did you know there are over 100 covered bridges in the small state of Vermont? People love covered bridges. Whether they love the significant history of them or just enjoy taking photos in front of them, people go nuts for them. Here are a few located in Bennington to check out.

  • Burt Henry Covered Bridge
  • Papermill Covered Bridge
  • Silk Road Covered Bridge
  • Chiselville Covered Bridge

Enjoy the Indoors (If the Weather is Bad)

If you’re visiting for a fall weekend and the weather is bad one day, Bennington has some good indoor staples: bowling and movies. Bennington Lanes is where I had (and attended) many birthday parties growing up, and Bennington Cinema 7 is where I hung out on weekends with friends. If spas are more your thing, check out Green Mountain Oasis.

Where to Eat in Bennington, Vermont

The Publyk House

The best part of the Publyk House is their salad bar. Even if you don’t like salad or don’t consider yourself a “salad person” (I mean, who IS a salad person?), you’ll end up piling your salad plate. My favorite items, aside from the fresh lettuce and veggies, are the salads (bean salads, macaroni salads, you name it), and the fresh baked bread. The variety of entrees are large – tons of seafood, chicken, and steaks to choose from.


Cilantro is a great spot for lunch for fresh, Mexican food. They have a range of tacos, burritos and salads, with plenty of options to choose from for each (meats, salsas, and toppings). The restaurant itself is nicely decorated – very simply and modern. I wish this place was around when I was growing up – this girl became a taco lover far too late in life.

Madison Brewing Company Pub & Restaurant 

Madison’s is great for beers and burgers (or just one of them, depending on what time of the day it is). I find the service to be a bit slow and spotty, but if you don’t mind that, it’s not an issue. There’s tons of beer on tap (and during fall, some seasonal ones), and if you want to try a little of each, get the sampler. For food, you can’t go wrong with their burgers (and their delicious fries). My go-to is their Tavern Burger.

Where to Stay in Bennington, Vermont

I’ve rarely “stayed over” anywhere in Bennington because it’s a 15-minute drive from my childhood home. But for those of you who are coming in from out-of-town, here are some options.


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