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Published: Sep 22, 2020
Connecticut Office of Tourism

Founded in the 1650s beside the picturesque Connecticut River (the longest in New England), this Hartford suburb boasts two separate districts on the National Register of Historic Places. These neighborhoods turn the north-south Main Street into a parade of Georgian and Greek Revival-style buildings that will make you feel like a character in a period movie.

For a town of just 27,000 residents, South Windsor has a lot to offer, including 10 public parks within city limits, featuring spaces for hiking, fishing, and bird-watching. If you’re a fan of fresh produce, there’s plenty in the area. Stefon Farms, for example, sells subscriptions for weekly boxes of local beets, tomatoes, cucumbers, herbs, and other veggies. Prices start at $370 for the 22 weeks between June and November.

South Windsor’s economy has remained relatively steady, in part thanks to large, stable employers in the Hartford metro region like insurers Aetna and The Hartford, as well as aerospace manufacturer Raytheon Industries, which employ a combined 21,000 people in the area. — Mayra Paris