TOP 10 vermont BIKING routes

We know you guys love biking. Well, we love biking too so we went ahead and created a super cool list of the best places to bike in Vermont. It took us about 10 years of trial and error (mostly error) to narrow in on our favorite places to bike in beautiful Vermont!

Manchester Center

Parking: Limited parking at the bike shop, or more plentiful spots at the Battenkill Plaza Shopping Center

Bike Rental: Battenkill Bicycles

Distance from Boston: ~3.5 hours

Manchester Center is a spectacularly scenic small town in south-western Vermont, tucked in just at the base of the infamous Green Mountains. Home to a number of notable locations including the historical estate of Robert Lincoln (son of the more well-known Abraham Lincoln), the American Museum of Fly Fishing, and the Southern Vermont Arts center, Manchester Center becomes a particularly popular destination in the Fall when visitors can witness Vermont’s colorful display of foliage.

Length: 8.5

Difficulty: Easy

Landmarks Passed: American Museum of Fly Fishing and beautiful scenery!

Rest stops: Several country stores in the first half, restaurants towards the end

Ride Type: Road

Starting out in beautiful Manchester Center, this road ride is scenic and only moderately hilly, sticking to the flattest terrain available in the area. For the first three and a half miles, the ride climbs very gently along Route 30, a quieter auto route, while passing by the Davis Family Deli. Turning around in the quaint town of South Dorset, the route doubles back for a mile before forking off onto the much smaller W Road. From here, cyclists can enjoy views of Equinox Mountain before the route loops back towards Manchester, passing by a number of restaurants including Mother Myrick’s Confectionery, a great spot for ice cream after a bike ride! In summer, the loop provides views of lush greenery, while in the fall cyclists can enjoy Vermont’s famous foliage!

Length: 18.5 miles

Difficulty: Medium

Landmarks Passed: South Village Pond, John Zaccheo Art Gallery, American Museum of Fly Fishing

Rest stops: East Manchester Center, Downtown Manchester Center

Ride Type: Road

Though undoubtedly as scenic as the South Dorset Loop, the Hills of Manchester route is a good deal more strenuous. Though relatively short, the route tackles three distinct climbs of different types. The Hills of Manchester ride sets out in the same way as the South Dorset Loop, allowing different riding groups to start out together. However, where the South Dorset route turns around, this route splits off to the right, descending towards the ride’s most difficult climb up Barnumville Road, ending at the base of beautiful Spruce Peak. In the fall, cyclists will catch a beautiful view of the foliage on the peak, though summer viewing is also spectacular. Riders then pass through east Manchester Center, a wonderful place to stop for a bit to eat, before the road kicks up one last time as it enters Manchester proper. From there, it’s a straight 1.5 mile run back to the starting location in downtown Manchester Center.

WOODSTOCK

Parking: High Grove Parking Lot at 12 Grove Street, Brattleboro

Bike Rental: Brattleboro Bicycle Shop

Distance from Boston: ~2 hours

In many ways the center of southern Vermont, Brattleboro is a small but bustling city located directly on the banks of the Connecticut River. With a host of local restaurants and businesses, Brattleboro is undoubtedly the most happening location on this list, and yet it is still home to scenic views that rival any tiny town in the mountains. With New Hampshire’s Wantastiquet Mountain looming large on the other side of the river, the view gives the feel of an Alpen valley, and the bicycling opportunities are something to behold.

Length: 11.5 miles

Difficulty: Medium

Landmarks Passed: The Woodstock Green, South Woodstock Historic District, Ottauquechee River, Daughters of the American Revolution Museum

Rest stops: South Woodstock, West Woodstock

Ride Type: Road

Starting and ending right next to the historic Woodstock Green, the Meetinghouse Hill Loop consists predominantly of the long climb towards South Woodstock and then, of course, the descent on the way back. The route on the way out follows the scenic Route 116, a local route that is both beautiful and friendly to cyclists. The road is mostly flat with only a slight upward pitch until the turnaround in South Woodstock when it ramps significantly up for about a mile of pain to the true top of the climb, the base of Meetinghouse Hill. After the peak, the route sweeps downwards, completely on local roads, until it meets the Ottauquechee River. From there it’s a short run along the river’s banks, followed by a quick and easy climb back towards town.

Length: 7.5 miles

Difficulty: Easy-Medium

Landmarks Passed: The Woodstock Green, Ottauquechee River, Daughters of the American Revolution Museum

Rest stops: Prosper, West Woodstock

Ride Type: Road

While the distance covered by this route may appear easy, even such a short ride is not exempt from the hills that define bicycle riding around Woodstock. Though Through the Valleys does its best to stick to the spaces between the hills, it still can’t help but climb a few. Luckily for those less excited about the climbing, the majority of the uphill is concentrated at the beginning, in the slow-but-steady two mile climb to the base of Hurricane Hill. At the top, riders will make a turn around in the the tiny town of Prosper before threading their way through a lush and beautiful valley on a long descent to the river. After crossing a bridge in West Woodstock, it’s an easy climb up Carleton Hill before the downhill back into Woodstock.

putney

Parking: At the bike shop

Bike Rental: West Hill Shop

Distance from Boston: ~2 hours

Located just north of the much larger Brattleboro, Putney is a quaint and historic town nestled right into the heart of Vermont’s Green Mountains. Though not traditionally a bustling spot for tourists, Putney is something of a well-kept secret, with vibrant business and rich history, all surrounded by picturesque wilderness. These spectacular views come at a price, however. There are few locations in the northeast where the bike riding is more challenging.

Length: 21 miles

Difficulty: Hard

Landmarks Passed: Putney Town Center, Kurn Hattin Hill, Connecticut River, Putney Mountain

Rest stops: Westminster, Putney

Ride Type: Road

The Kurn Hattin ride has a single centerpiece: the Kurn Hattin Road climb. Climbing 590ft in just over two miles, Kurn Hattin Road averages a 5% gradient, but kicks up to a whopping 14% and more, with the most difficult pitches coming right in the final. The Kurn Hattin ride, however, is more than a mere procession to and from its namesake hill. Scattered throughout the trip down southern Vermont’s scenic backroads, riders will find a plethora of short, steep climbs that the region is famous for. Thankfully Kurn Hattin is not all work; while the first half of the ride is dominated by climbing and arduous false flats, the second half spends most of its time winding downhill through southern Vermont’s backwoods towards the base of Putney Mountain. Just under a mile from the finish back at the bike shop, the route also passes through Putney’s town proper, giving the perfect opportunity for a bite to eat before calling it a day.

Length: 12 miles

Difficulty: Medium

Landmarks Passed: Putney Mountain, Connecticut River, Putney Town Center

Rest stops: No towns passed, but plenty of scenic outlooks!

Ride Type: Mixed Gravel and Paved Road

The Tamer Tour features perhaps the best examples of the terrain southern Vermont is known for: gravel roads. Though a bit tricky your first time, riding on gravel adds an exciting level of challenge to road cycling, as well as opening up whole new areas of wilderness untouched by pavement. The Tamer Tour’s ascent of Putney Mountain’s base is a perfect example of this. After setting out from Putney’s Town Center, the route slowly drags up Westminster Road, before taking its first into the real climbing. The first climb of the mountain’s base leaves riders at a stunning overlook point and, following a short descent, the second time up brings the route to locations even higher and more beautiful. From there, cyclists will bounce up and down some short but steep hills, before a luxurious descent back down towards Putney.

Brattleboro

Parking: High Grove Parking Lot at 12 Grove Street, Brattleboro

Bike Rental: West Hill Shop

Distance from Boston: ~2 hours

In many ways the center of southern Vermont, Brattleboro is a small but bustling city located directly on the banks of the Connecticut River. With a host of local restaurants and businesses, Brattleboro is undoubtedly the most happening location on this list, and yet it is still home to scenic views that rival any tiny town in the mountains. With New Hampshire’s Wantastiquet Mountain looming large on the other side of the river, the view gives the feel of an Alpen valley, and the bicycling opportunities are something to behold.

Length: 6 or 4 miles

Difficulty: Easy

Landmarks Passed: Brattleboro City Center, Living Memorial Park, Whetstone Park, a real Vermont covered bridge!

Rest stops: Nearly anywhere along the route

Ride type: Road

The Brattleboro City Loop offers a relaxed tour of the city’s neighborhoods and scenic views. Though the route is not without hills (they’re impossible to avoid in Brattleboro), it is all within a manageable 6 miles (or 4, if you cut out the first loop next to Brattleboro Hospital) and never strays far from its starting point, making it easy to end the ride at any time. Starting out in Brattleboro’s historic downtown, cyclists will climb up to southern Brattleboro, before turning into the less populated area of the city, beautifully built into the side of a hill. The route cross Brattleboro’s small offshoot river that runs through the center of the city at Living Memorial Park, an important destination for world-class athletes because of its Olympic-grade ski jump. From there, the route winds back towards town, staying close to the river before the final ascent up Main Street to the finish.

Length: 12 miles

Difficulty: Medium

Landmarks Passed: Brattleboro City Center, Living Memorial Park, Whetstone Park, a real Vermont Covered Bridge!

Rest stops: Guilford, anywhere in Brattleboro

Ride type: Road

In many ways, the Guilford Tour emulates the City Loop route, just this time with a little extra challenge thrown in! The route starts out in Brattleboro’s downtown, climbing first to the southern area of the city, before taking a turn west. From there, cyclists will face a moderate climb out of the city, before a descent into the small town of Guilford. From there, it’s a straight shot on Route 5 to return to Brattleboro, where cyclists will face a short loop by a number of parks before one final challenge: Union Street, the steepest in the city. With gradients approaching 20%, the short, punchy climb will make the finishing descent back to Brattleboro’s Main Street feel well deserved indeed.