Choose wisely. Connect locally.Add your business 
Windsor claims the title of Connecticut's oldest English town: traders from Plymouth Colony built a post here in 1633 where the Farmington River meets the Connecticut, and Puritan settlers from Dorchester followed soon after. Their palisaded village is remembered on Palisado Green, and the congregation they brought with them still meets at the First Church in Windsor.
For three centuries the river meadows grew shade tobacco used for cigar wrappers, and the white tobacco sheds that once dotted the fields are explained at a museum in Northwest Park. Oliver Ellsworth, a framer of the Constitution and the third Chief Justice of the United States, lived at the Elmwood homestead, now a National Historic Landmark open for tours.
Today the town is a leafy Hartford suburb with a lively green on Broad Street, the Windsor Shad Derby festival each May, and miles of trails along the rivers. Hartford is ten minutes south and Bradley International Airport just to the north.
A large town park of forest, meadows and wetlands with about twelve miles of trails, a nature center with live animals, an animal barn and boardwalks over bogs. Winter brings cross-country skiing and a maple sugaring weekend. Start at the nature center for trail maps and seasonal program schedules.
Set inside a tobacco shed in Northwest Park, this museum tells the story of the shade-grown and broadleaf tobacco that dominated the Connecticut River Valley for generations. Displays show tools, curing methods and photos of farm workers. It opens on limited days, so check hours before planning a visit.
The society runs a small museum and two historic houses on Palisado Avenue, including the eighteenth-century Strong-Howard House and the Dr. Hezekiah Chaffee House. Exhibits cover the 1633 settlement, river trade and tobacco farming. Guided tours of the houses leave from the museum during open hours.
Known as Elmwood, this 1780s farmhouse was the home of Oliver Ellsworth, a delegate to the Constitutional Convention, senator and the third Chief Justice of the United States. Rooms hold period furniture and family items, and George Washington visited in 1789. It is open on summer weekends for guided tours.
This quiet triangle of green marks where settlers built a protective palisade around their homes in 1637. A monument honors the town's founders, and historic houses line the surrounding streets. Pair it with the old burying ground behind the First Church, which holds some of the oldest gravestones in Connecticut.
The congregation was organized in England in 1630 and came to Windsor with its first settlers, making it one of the oldest in the country. The white Federal-style meetinghouse dates from 1794. Walk through the adjacent Palisado Cemetery, where slate stones from the 1600s carry early winged skull carvings.
The long green along Broad Street is the heart of Windsor, with a fountain, war memorials and shade trees, and is lined with the town hall, shops, cafes and restaurants. Farmers markets and festivals fill it in warm months. The train station is a short walk away, making it an easy car-free stop from Hartford.
A small state park on the west bank of the Connecticut River with a riverside path, fishing spots and a launch for canoes and kayaks. It sits close to downtown Hartford yet feels secluded. Bring binoculars for herons and eagles along the river, and avoid the low areas after spring floods.
A spring festival held on the Broad Street Green since the 1950s to celebrate the shad run up the Connecticut River. Expect a parade, crafts, food vendors, live music and a fishing contest for the biggest shad. It is held in May; arrive early on festival Saturday, since parking near the green fills quickly.
Top-rated local businesses in Windsor, with real reviews on WiserMap.
No reviews yet. Been to Windsor? Be the first to share your experience.
Share what you loved, what to skip and tips for other travelers.
Log in to write a reviewBeen to Windsor? Add your best shots to the gallery.
Log in to add photosPhoto: –Grondemar, Wikimedia Commons, CC BY-SA 3.0
Photo: John Phelan, Wikimedia Commons, CC BY-SA 3.0
Photo: Chrissypan, Wikimedia Commons, Public domain
Photo: Chrissypan, Wikimedia Commons, Public domain
Photo: Chrissypan, Wikimedia Commons, Public domain
Photo: Daderot, Wikimedia Commons, CC0
Photo: Daderot, Wikimedia Commons, CC0
Photo: John Phelan, Wikimedia Commons, CC BY-SA 4.0
Photo: John Phelan, Wikimedia Commons, CC BY-SA 3.0
Photo: John Phelan, Wikimedia Commons, CC BY 4.0
Photo: John Phelan, Wikimedia Commons, CC BY 4.0
Photo: John Phelan, Wikimedia Commons, CC BY-SA 3.0
Photo: John Phelan, Wikimedia Commons, CC BY-SA 3.0
Photo: Elipongo, Wikimedia Commons, Public domain
Photo: John Phelan, Wikimedia Commons, CC BY 4.0
Photo: Daderot, Wikimedia Commons, Public domain
Photo: Daderot, Wikimedia Commons, CC0
Photo: Daderot, Wikimedia Commons, CC0
Photo: Daderot, Wikimedia Commons, CC0
Photo: Daderot, Wikimedia Commons, CC0
Photo: George Neat, Wikimedia Commons, CC BY-SA 4.0
Photo: George Neat, Wikimedia Commons, CC BY-SA 4.0
Photo: John Phelan, Wikimedia Commons, CC BY 4.0
Photo: Daderot, Wikimedia Commons, Public domain
Photo: –Grondemar, Wikimedia Commons, CC BY-SA 3.0
Photo: Daderot, Wikimedia Commons, Public domain
Photo: Daderot, Wikimedia Commons, Public domain
Photo: Daderot, Wikimedia Commons, Public domain
Photo: Daderot, Wikimedia Commons, Public domain
