Sites, scenery, and surprises: Bennington, VT

When my parents came to visit in April, my mom, being the chatty Cathy she is, spent her plane ride talking to a longtime local of Upstate NY who recommended we all visit a tiny town right outside the New York border called Bennington. My mom (who loves lists) then decided to add another state to her “States Visited” list, and the itinerary for the weekend was set: we were heading to Vermont.

img_8276My parents and I hit the must-see monuments, admired the small-town New England charm of downtown and the historic district, stopped at a chocolate shop, grabbed some VT souvenirs, and headed back to NY. Though short and a little cold (April in the North, you know), the trip was very worthwhile, and we all got a chance to explore somewhere new.

This weekend, a friend I made in college came to visit with the same goal in mind: to visit a state she had never been to, and Vermont would be a new one for her that is only a day trip away. So where was I thrilled to take her? Bennington!

For the second trip, the weather was warmer, we visited earlier in the day, so the shops were open, and I was able to look past the historical signs and appreciate the little town for its lovely [seemingly] happy, family-oriented nature. Everywhere I looked I saw children or people walking their dogs. I saw houses with bikes outside and the shops and restaurants were full of people chatting with one another. It felt like somewhere I would want to live for a life with a slower pace.

UPDATE: I ended up visiting Bennington a third time with my friend who was thru-hiking the Appalachian Trial. The little town is right on the trail, and after seeing this blog post, she asked if I wanted to meet up with her there. I highly recommend it as a day-stop if you’re hiking that part of the AT!

I enjoyed my time there, and I feel like you would too. Here’s my guide on where to go and what to see around Bennington:

Bennington, VT


Known for its pride in its historical significance (*cough* in the Revolutionary War) and its employment of representative town meetings as the local government, Bennington comes across a lot like Stars Hollow from Gilmore Girls (a great description of the real town Stars Hollow was based on can be found here). Though there was no Town Square, Bennington’s downtown and Old Bennington district turned on all the charm with locally grown stores and restaurants and Vermont/Bennington themed everything in the gift shops. Bennington is quaint, it’s cute, and it has a lot to see and do.

What to see and do:

For the historically focused, The Bennington Monument is a tall reminder that the soon-to-be Americans won of The Battle of Bennington in the Revolutionary War (you can read about the battle here). There is also a historic district known as Old Bennington that is home to the most beautiful colonial houses. I would highly recommend taking time to drive through there and admire all of them (you know I did). In Old Bennington, there are also various monuments dedicated to the historical figures of the war and the beautiful and dangerous VT catamounts. One warning I have for anyone visiting the Monument and wanting to do some walk-exploring, there is an adorable little building near the monument called “The Barn”, that we learned is not meant to be open to tourists unless you’re looking to join a new place of worship (oops!) – it is a building now owned by the Old First Church of Bennington.

As a lover of old things (though not necessarily historical), I also made time to do some antiquing at a couple of lovely stores: Antiques at Camelot and the antique store attached to the Vermont Confectionery (yum!). Bennington also has a vast selection of covered bridges for visitors to use and enjoy. If you aren’t interested in old things, but you still like to find local treasures, many visitors like to stop by the Bennington Pottery Factory.

img_8283During both trips, I made a point to visit Downtown Bennington, each with a chance to see different shops along the street. During the first visit, my family visited The Village Chocolate Shoppe, where they have a chocolate cow (!!) and some incredible sweets to choose from – we may or may not have gotten an entire 1lb box full to share (hint: we did, and I’m still nibbling on them weeks later because I don’t want them to end). With my friend, I had a chance to visit the local book shop, a board game shop (that sells $4 DVDs. Score!), and my personal favorite, an adorable local-everything shop: Bringing You Vermont. I cannot recommend this little shop enough – the manager was so nice and willing to tell us everything about the quaint town as well as where to go to see the sights. He also introduced me to my new favorite pancake condiment, Hickory Syrup!


We didn’t eat too much in Bennington, but I can definitely recommended the places where we did eat.

I mentioned above the Vermont Confectionery – there were so many ice cream options I didn’t know what to choose. What I did get was absolutely wonderful and I would definitely recommend stopping there if you take the NY to VT route. While Downtown, we stopped into the Madison Brewing Co. (incredible food!) and a lovely coffee shop that was recommended to me from a local, which was another great spot.

I hope you have a chance to visit the adorable town of Bennington! The incredible views of Vermont mountains paired with the quaint small-town atmosphere make for a relaxing and wonderful trip. I’m always looking for new places to see, and even if it’s just new things in a place I’ve been, I’ll put them on my list for next time. If you’ve been to Bennington or are planning a trip there or elsewhere in Vermont, I’d love to hear about your travel in the comments!

Disclaimer:  I was not paid or given any freebies for promoting these local businesses. These are my personal reviews and preferences, so keep that in mind when ordering your tickets or reserving your table. But also shop local!

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