Woodstock, Vermont - Sherman Cahal
Woodstock is a drop-dead gorgeous village in Vermont that is set among the banks of the Ottauqueechee River.
Woodstock, Vermont
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Woodstock, Vermont

Woodstock is a drop-dead gorgeous village in Vermont that is set among the banks of the Ottauqueechee River. Named “The Prettiest Small Town in America” by the Ladies Home Journal magazine, the streetscape is lined with general stores, farmers markets, and booksellers. It evokes a far simpler and slower time.

I arrived with fellow landscape photographer Matt Shiffler on a deep overcast morning. From our route along the winding Ottauquechee, the quaint family farms give way to modest cottages and small businesses. Those too made room for quintessential white churches that dot the New England landscape and then the town square. Named “The Green,” it was bookended with late-Georgian, Federal style and Greek Revival residences and multistory downtown businesses. It was the park to take in 19th-century nostalgia.

Early Woodstock was defined by its mills along the Ottauquechee. By the mid 19th century, factories surrounded the town, manufacturing carriages, furnishings, farming implements, woolens, and carding machines. That gave way to tourism, thanks in part to the Rockefeller family who invested much time and money into the community. Resources were spent burying power lines, restoring historic buildings, and encouraging smart planning policies. This helped preserved the town’s aesthetics and its surrounding countryside.

With the midday approaching, we said our goodbyes to Woodstock and hit the roads.

shermancahal
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