Litchfield Hills B&B Bike Trails, North Canaan to Woodbury
One of eight Connecticut B&B Bike Trails (all with bed-and-breakfasts along the way), this 97-mile road route takes you through the foothills of the Berkshires, the Housatonic Meadows, and Dennis Hill State Park. The route is rated moderate to difficult, with lots of hills and low mountain ranges.
Bicycle Route 1, Montchanin to Fenwick Island
Bike from one end of the state to the other on this scenic route that passes beaches, dunes, boardwalks, marshes, and even World War II submarine watchtowers. The entire route stretches 150 miles from the Pennsylvania border to Maryland; the last section, from Rehoboth Beach south, runs along the coast. You’ll share the road with cars, but the generous shoulder provides security for two-wheeled travelers.
Jacksonville-Baldwin Rail Trail, Jacksonville to Baldwin
This 14.5-mile paved asphalt trail gets you away from the noisy city and deep into the woods. It’s a popular route for road and recumbent touring bikes, although the 20-mph speed limit keeps everyone to a recreational pace. The trail abuts Camp Milton Historic Preserve, an important Civil War site.