Windsor, VT

Set right along the western bank of the Connecticut River, Windsor offers a classic Upper Valley lifestyle with a relaxed, small-town pace. Home to around 2,000 residents, the village blends walkable historic streets with easy access to outdoor recreation at nearby Mount Ascutney. One of the area's most recognizable landmarks is the Cornish-Windsor Covered Bridge, the historic wooden span connecting the town directly to Cornish, New Hampshire across the water.

ATTRJohn Phelan / CC BY-SA 4.0

Windsor also holds a proud place in state history as the birthplace of Vermont, where delegates signed the state's first constitution back in 1777 at the Old Constitution House. Today, that heritage sits comfortably alongside local breweries, artisan shops, and scenic riverside parks. With its handsome brick architecture, quiet neighborhoods, and straightforward commute to Upper Valley employment hubs, Windsor is a warm and practical landing spot for anyone moving to the region.