It took me 3 years of living in New England to realize that spring and fall are by far the best times to travel. Summer is hot and humid and everything is crowded. Winter is cold and miserable. But in spring and fall, the weather is usually decent, crowds are drastically diminished, and entrance fees are often cheaper in the off-season.
Case in point: Pat and I visited Bennington, Vermont one March and had a nice, sunny – albeit slightly chilly – weekend.
The idea to visit Bennington began courtesy of Groupon, when I stumbled across a discount reservation at the Harwood Hill Motel. From what I gathered from internet reviews before booking, it was (as of March 2016) purchased by new owners who were in the process of sprucing the place up. Our room was newly painted, and they were clearly still working on renovations; the woman who checked us in was wearing paint-covered overalls.
Though by no means a fancy place, our room was nice and we enjoyed our stay.
We didn’t actually know that much about Bennington, and figured we’d just arrive with no real plan and wander around the town. A quaint town of 15,000 people located in southwestern Vermont, Bennington is full of history. The most obvious example is very visible, as it rises 300 feet above the town: the Bennington Battle Monument.
This giant stone obelisk commemorates the Battle of Bennington. This Revolutionary War battle actually took place across state lines on the Bennington Battlefield in upstate New York, but the stash of food and armaments that the British army was attempting to raid was located at the present day site of the monument. The British were ultimately unsuccessful, as American General John Stark and his men prevailed.
Because it was the off-season, we weren’t able to go up in the monument (from the top, you can apparently see into New York and Massachusetts), but we were still able to wander the grounds and learn the relevant history of the battle.
Next, we made our way to the historic Southern Vermont and Bennington Colleges, the former of which somewhat resembled Hogwarts and the latter of which looked like an old farm turned university.
On the way to the colleges, we passed through the most historic section of Bennington, home to the town’s first church, cemetery (where Robert Frost is buried), and row of houses.
Downtown Bennington has definitely retained much of its historic charm over the years, with brick storefronts and just an overall quaint New England feel. We wandered the main street and then escaped the chilly breeze for burgers and beers at Madison’s Brewery.
One thing I’d been completely unaware of is the fact that Bennington has quite a long history with pottery. The most well-known place is Bennington Pottery. In fact, the Bennington Potters Yard is open to the public; we were able to walk through on a self-guided tour and learn about the pottery making process. It was a weekend, so there weren’t a lot of employees there, but we did see one or two working on various parts of the process. All of their pottery is handmade, and they have some truly unique, very ergonomically designed pieces. In fact, Pat loved one of their mugs so much that he now drinks coffee from his very own quite frequently!
Satisfied and wind-blown, we headed back to our hotel, taking a mini detour along the way. Vermont and New Hampshire are known for their covered bridges, many of which are still safe to drive across. There are 3 in the Bennington area, so we took a winding route to our motel, allowing us to drive through all 3 of them (though apparently I only took photos of 2 of them…)
All in all, we very much enjoyed our time spent in Bennington. We learned a lot of history, dodged the crowds, had some tasty beer, and then drove the scenic Highway 9 (Molly Stark Scenic Byway) through the Green Mountains on our way home, stopping at the summit overlook from which views extended all the way to Massachusetts and New Hampshire!
This was also the inaugural trip for Cora, my new (to me) car, and she handled it like a pro. After a very rough final few months with my old car, it was so nice to be able to drive without the constant fear of breaking down at any time.

She and I have now been to 23 states together…only 27 more to go!
I loved my trip to Vermont, and it was a lot like this- Brattleboro in the winter and making it up as we go! Beautiful state. Your post made me want to go back for sure.
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Thanks so much for reading! I hope you make it back to Vermont soon!
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