VT 251: Bennington, Sunderland, Searsburg, and Woodford
- donnaramadishes
- Sep 21, 2023
- 2 min read
Updated: Sep 18
In September 2021, I explored 4 rural and historic towns in southwestern Vermont as part of this VT251 exploration. These Bennington County towns hug the Massachusetts and New York borders.
BENNINGTON
Bennington, the most populous town in southern Vermont, is quaint and rife with charm, revolutionary history, covered bridges, a college, a museum, and an active downtown. It was chartered in 1749, making it the oldest town in the state to be chartered, and settled in 1761. It is home to the Bennington Battle Monument (the tallest man-made structure in the state), which commemorates the Battle of Bennington that ironically actually took place in nearby New York. The battle was fought during the revolutionary war (1777) and involved Ethan Allen's militia known as the Green Mountain Boys, who defended the land against German mercenaries fighting for England. North Bennington used to be a real town with its own (well-preserved) train station, but is has been subsumed by Bennington proper, and is therefore an unofficial town today.
What to do in Bennington? Well, you can eat and shop in downtown, go to The Bennington Museum (home to the largest collection of Grandma Moses paintings), visit the resting place of Robert Frost, visit the Bennington Monument (maybe the elevator or stairs will be open to the public so you can see the great view from the top), check out Bennington College, or visit any or all of its three covered bridges. Typical of the state, there are some good brew pubs (Madison Brewing is my fave, although I have not tried 421 Craft Bar & Kitchen which I've heard good things about). There's a yummy chocolate shop with a giant chocolate moose, a beloved diner, The Blue Benn, and Bennington Pottery is a fun store to browse through in person if it is open -- but you can also shop their wares online. Oh, and if you happen to find yourself in the area around Labor Day, Bennington hosts a garlic festival which is stinky (in the best possible way) and a lot of fun.
SUNDERLAND
Sunderland is a lovely, small village in Bennington County (pop ~1,000 in 2020), without much to see other than the Chiselville Covered Bridge and the fact that Orvis' headquarters are apparently located there.
SEARSBURG
There's not much to say about Searsburg, other than that it is TINY (pop 126 in 2020!), was chartered in 1781, and apparently dropped out of existence for the first quarter of the 19th century (ie no land title transfers of record)! Perhaps its questionable past existence explains its minuscule population and the fact that, apart from town offices, not much seems to exist there today.
WOODFORD
Similarly, the town of Woodford is tiny (pop 355 in 2020) and currently does not have much visible commerce. It was chartered in 1753, making it one of the oldest towns in the state, and it currently sports a general store, lovely vistas, and a cemetery with the request that snowmobiles stay out. Apparently at some point there was another town, Woodford Hollow, which had at least a school house...
Stay tuned for more!
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