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Simsbury, Connecticut: A 1-of-a-kind road trip to a 1-of-a-kind town

Simsbury is about one-third open space or preserved farmland and is a "Preserve America" community.

Lori Golias

Jul 24, 2025, 7:18 AM

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Truly a unique town, and full of one-of-a- kinds — Simsbury is the only Simsbury in the United States.

The town is home to the the largest tree in Connecticut, the Pinchot sycamore.

Simsbury is about one-third open space or preserved farmland and is a "Preserve America" community. The town was recognized by the National Trust for Historic Preservation as one of its "Dozen Distinctive Destinations."

Simsbury, Connecticut, was recognized as the state's first "Bicycle Friendly Community" by the League of American Bicyclists.

The Simsbury Meadows hosts many summer concerts and is the summer home of The Hartford Symphony Orchestra.

Certainly for many, the Old Drake Hill Flower Bridge might be a destination in itself. One of only three Parker truss bridges remain in the state. Volunteers and friends tend to the over 70 flower boxes, 30 hanging baskets and 14 border column baskets that adorn the bridge all summer long. There are also many concerts and gatherings at the bridge that spans the Farmington River.

The iconic 165-foot-castle-like Heublein Tower stands atop Talcott Mountain overlooking the Farmington River Valley. Take a mile and a half hike up to explore.

The town, founded in 1670, is full of history. You can spend time exploring centuries of stories at The Simsbury Historical Society.

Simsbury is a great town for hiking, biking, dining, shopping and more, where a day trip might turn into a weekend...or more.

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