Make a selection below to view suggestions for a southern Vermont biking adventure. Find southern Vermont bike trails, bicycling routes, and cycling locations for every skill level. To feature your Vermont bicycling or sporting business in Vermont Living Magazine, contact us.
The State of Vermont is home to hundreds of miles of mountain biking trails and bicycle routes. Come to Vermont to ride, explore, and improve your mountain biking skills, take a guided bike tour, or find a dirt road and make your own bicycling route!
Southern Vermont Area Bicycle Routes
Chester-Cambridgeport Loop, Chester, VT - 26 Mile Loop - Moderate Rating
Travel through picturesque historic towns beginning on Main Street in Chester and continuing straight onto SR 103 South for approximately six miles before turning South onto Pleasant Valley Road. The trail bears right at the intersection with SR 121 and follows a narrow and winding, yet fairly flat, stretch to the town of Grafton. Trail then turns right onto SR 35 North, traveling back to Chester and turns right again onto SR 11 to return to the starting point.
Dorset-Rupert-Pawlet Loop, Dorset, VT - 30 Mile Loop - Moderate Rating
This scenic ride through the Vermont countryside is a popular mountain biking excursion. The route travels North on SR 30 to Pawlet and continues two miles farther North before turning left onto a Secondary Road that follows the Mettawee River to the intersection with SR 153. The trail turns left and heads South to Rupert, traveling through beautiful countryside on SR 30 to East Rupert before returning to the starting point in Dorset.
Mount Snow, West Dover, VT - 140 Mile Network - Easy to Difficult Rating
Mount Snow is the first Vermont ski area to promote mountain biking, and is known as the area's 'Mountain Bike Capital'. For a modest fee you can access Mt. Snow's 3,556 foot summit via chairlift. Mt. Snow also offers a Mountain Biking School.
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