Find the top rated mountain biking trails in Cheshire, whether you're looking for an easy short mountain biking trail or a long mountain biking trail, you'll find what you're looking for. Click on a mountain biking trail below to find trail descriptions, trail maps, photos, and reviews.
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Rode October 2026, easy access off 84, beautiful Fall day, scenery is varied, paved surface was flawless.
Easy access, clean blacktop and nearly unlimited distance in either direction! Outside of the Morgan Park entrance this is the best bet!
Decent walk and view. As of October 2026 bathrooms are not open ever.
Rode Pawley Trailhead to Hopewell Junction and back. Perfect, smooth, clear, pavement. No downed trees . Few easy road crossings, shady throughout. Nice lunch at Daddy Os in Hopewell Junction.
We did this trail in two days. We learned that it is not quite complete from Hillsdale to Wassaic. Trail is closed from Black Grocery Road to Orphan Farm Road about 1.5 miles. So be warned that as of Sept 15 you can’t quite go completely through YET. Above Millerton and below are almost two completely different trails so we were happy to be able to stop and explore at our leisure. Above is really farm and marsh lands while below has more towns and historical things to see and do. Millerton, has many places to eat and a great mid stop. The leaves are not turning yet but will be beautiful in the colorful fall. I heartily recommend the ride.
This rider was going Northeast from Willimantic towards Hampton NOT Southwest from Willimantic to East Hampton. Having ridden both stretches I can say his description is completely wrong about the gorgeous and open riding Southeastern route and not completely wrong but somewhat overly harsh about his route which can get iffy for stretches.
Rode entire trail roundtrip on a sunny August day. It's a great trail with a great paved surface. Scenic, too. The southern trailhead (Wassaic) has a direct train connection to New York City, so it's just a matter of time before it's discovered by folks from the city for a day's ride.
Town of Millerton in center of trail had the best facilities for a mid-ride break. Copake Iron Works Museum at Taconic State Park and close to the trail also well worth a visit.
Hubby & I went this morning for a trial run with my new e-bike! It was tons of fun!!!!
Mostly cinder. Started from access lot off of RT 7. Shared RT Trail with the Town Of new Milford. Parallels an active track. Good variety of terrain and scenery..
Wonderful trail. Part of the larger Empire State Trailway. This part from Eastview to Baldwin Place is the section I ride the most. Mostly shaded once you're north of Millwood with plenty of spots where you can stop for a bite or veer off for road riding near the reservoirs.
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