Cycling in Simsbury

Simsbury is one of Connecticut’s easiest cycling towns to love, because the riding is flat, paved, and starts almost anywhere. The Farmington Canal Heritage Trail runs the length of town along the Farmington River — part of a rail-trail that traces the 1820s canal towpath from New Haven all the way to the Massachusetts border. Through the Farmington Valley it’s smooth asphalt, wheelchair- and stroller-friendly, and shaded, threading past restored canal locks, old rail structures, and river views with barely a hill in sight.

What makes Simsbury a genuine base rather than a trailhead is the parking and the connections: more than 300 free spaces line Iron Horse Boulevard, and the trail links to the Farmington River Trail to form a longer loop for riders who want to string together a real day out. Beginners and families can ride out and back for miles without touching a road.

The town’s two historic inns lean into it. The Simsbury 1820 House and The Simsbury Inn — both about a fifth of a mile from the trail — advertise complimentary hotel bikes guests can pedal straight from their room doors onto the rail trail. For everyone else, The Bicycle Cellar sits directly on the path at 532 Hopmeadow Street with rentals, full shop service, and Pedego e-bikes under the same ownership.

Ride here April through October, when the tree canopy over the trail is at its best; confirm the inns’ bike programs when you book, since the loaner fleets are seasonal.