Diverse Directions Cycling Tours
Self-Guided Bike Tours in Vermont & Neighboring States

Vermont Cycling Tour Itineraries

Vermont Outdoor Adventurist Tour

General Information

Location & Tour Highlights

Tour Dates

You may schedule your tour to begin on any date during our tour season, which extends from May 1 through October 31. See Scheduling Your Bike Tour for scheduling considerations.

Length & Format

4-stage circuit tour requires a minimum of 4 days / 5 nights. Spend as many days as you like in overnight destination.


With the exception of a very challenging 3-mile climb in stage 2 with an average grade of 6.2%, this tour's cycling itinerary is moderately challenging to challenging. There are long stretches of moderately rolling terrain, often on quiet dirt roads. You may forego the most difficult 3-mile climb in favor of a shuttle with your bikes. There is no additional charge for this when you rent bikes from us.


99 miles in 4 stages plus miles of optional cycling. Average of 25 miles per day.


Southeastern Vermont's lovely and historic Windham and Windsor Counties, and small portions southwestern  New Hampshire. The tour starts and ends in Brattleboro, Vermont. See Getting to Brattleboro for transportation options to the tour's starting point.


  • Overnight destinations: Brattleboro, Grafton, Jamaica, & Bellow Falls
  • Historic covered bridges
  • Gorgeous scenery
  • Visits to quintessential Vermont and New Hampshire villages, including Grafton, Jamaica, Walpole (NH) and Newfane, among New England's most beautiful
  • Opportunities to supplement your cycling with hiking, swimming, canoeing, and other activities

*The route map is only a close approximation of the tour's route and is not intended for navigation purposes. It is provided to show the area covered by this tour's itinerary.

Daily Itinerary
Arrival Day: Free Day in Brattleboro. Sightsee, Canoe, Kayak, Dine, Relax. Spend 1 or more nights. photo

You may arrive in Brattleboro at the time of your choosing, as there are no activities planned for your arrival day. Of course, the earlier you arrive, the more time you have to take advantage of the sights and charms of this wonderful New England town.

Brattleboro is a lively southern Vermont arts and cultural center ideal for window shopping, gallery hopping, people watching, participating in a walking tour, canoeing on the Connecticut River, hiking the trails of the Brattleboro Retreat or visiting the Retreat's Petting Farm, buying Vermont handcrafts, relaxing over a locally brewed beer, catching a movie or some live music, and of course, enjoying any one of a variety of exciting eateries and fine restaurants.

Accommodation options for your stay in Brattleboro include a downtown 1930's art deco style hotel, several lovely bed and breakfasts, and for the budget-minded, a variety of motels. View Brattleboro's accommodation options.

Stage 1: Cycle from Brattleboro to Grafton - Distance: 31 miles. Spend 1 or more nights.

photoFollowing breakfast you'll attend a brief orientation at your hotel or B&B, test ride your bicycle, and then begin your first day's journey from Brattleboro to Grafton.

Following the crystal clear waters of the West River, you'll pass cascading waterfalls and the West Dummerston Covered Bridge, the first of five historic covered bridges you may see on this tour, and Vermont's longest covered bridge still in use. A little further upstream you pass through Newfane, the loveliest of Windham County's so-called 18th Century "White Villages." (Virtually all of Newfane's buildings and homes are white, from the grand, Federal-style courthouse to the smallest private home.) Newfane is the ideal place to stop for lunch and explore the beautiful buildings along the village green.

From Newfane your route hugs the river valley between two mountain ranges, with beautiful views of the hills and farms of tiny Brookline. Beyond Brookline, the pavement ends  and you cycle through a deep, canopied forest where you'll feel you have left all 21st century cares behind. And just when you think life can be no better and you can take no more beauty, you arrive in Grafton. Grafton is one of Vermont's most beautiful villages and is like a trip back to a simpler time. Its setting amidst the hills and river is magnificent, as is the restoration of its historic structures. View Grafton's accommodation options.

Optional Free Day(s) in Grafton

photoShould you decide to spend two nights in Grafton we offer for your second day a 25-mile cycling loop over quiet, wooded back roads, passing small farms, a covered bridge, and quaint villages like Cambridgeport and Saxtons River.

If you prefer activities other than cycling, you may choose to stay closer to home, just soaking in Grafton's beauty, or taking the short half-mile ride to the Grafton Village Cheese Company, the Grafton covered bridge, and Grafton Ponds Outdoor Center. Grafton Ponds offers mountain biking and hiking, as well as guided canoe excursions and fly-fishing clinics.

Stage 2: Cycle from Grafton to Jamaica / West Townshend - Distance: 21 miles - Spend 1 or more nights.

photoToday's stage is all about rustic beauty. Your route begins with a gradual climb into the hills surrounding Grafton, along rushing streams and gorgeous landscapes. After an exhilarating descent, you return to the West River Valley and enjoy a gently rolling ride to Jamaica and its beautiful state park.

Accommodation options for your stay in Jamaica / West Townshend include several lovely inns and two country bed & breakfasts. View Jamaica's accommodation options.

Optional Free Day(s) in Jamaica / West Townshend

photo If you choose to spend multiple nights in Jamaica / West Townshend, you'll have a variety of activities from which to choose. On the Jamaica side, we highly recommend an easy to moderate 5-mile roundtrip hike to Hamilton Falls, Vermont's highest waterfall, or hiking the easy riverside trails in Jamaica State Park -- with plenty of spots ideal for a refreshing afternoon swim.

Just east of Jamaica additional hiking opportunities avail themselves in Townshend's two wonderful parks: Townshend Lake and Dam Recreational Area and Townshend State Park, adjacent to the Scott Covered Bridge, the longest wooden span covered bridge in Vermont. Or you may choose simply to explore the tiny village of Jamaica with its craft and antique shops.

Stage 3: Jamaica / West Townshend to Bellows Falls - Distance: 22 miles. Spend 1 or more nights.

photoToday's ride follows the course of the West River to pretty Townshend, with one final opportunity to admire the Scott Covered Bridge. From Townshend's perfect village green, you'll head north into the deep forests, following rushing streams until you reach the Saxtons River, which you'll follow for the remainder of your cycling day. If you didn't have the opportunity to visit the village of Saxtons River when in Grafton, don't worry. You'll see it now en route to the day's final destination.

Bellows Falls was a manufacturing powerhouse in the 19th century, putting to use the massive energy of the falls for which it is named. The old factories are mostly gone now, but the vestiges of that prosperous era remain in the Victorian mansions that comprise the town's registered historic district. (You can even overnight in one, if you wish.) Bellows Falls is a wonderful place for strolling and soaking in the New England atmosphere. The village even provides a walking tour of the historic district.

Accommodation options for your stay in Bellows Falls include two B&Bs and an economy motel. View Bellows Fall's accommodation options.

Optional Free Day(s) in Bellows Falls Area with Optional Cycling.

photoWe encourage you to spend at least two nights in the Bellows Falls area to take advantage of additional cycling in the area. You have the choice of two day-trip rides: (1) a moderately challenging 29-mile ride through deep forests and sleepy New Hampshire villages, which includes the opportunity to visit historic Charlestown, NH and a restored 18th century fort; and (2) an easy 11-mile ride to Walpole, one of New Hampshire's most beautiful villages and home to locally renowned Burdick's Chocolates.

There are also a myriad of non-cycling activities available -- kayaking (whitewater or slow moving), rock climbing, propelling, river gorge exploration, and hiking. Or you can spend the day looking at Indian petro graphs by the river, browsing in the local shops, and strolling the streets to become more familiar with the charms of Bellows Falls.

Stage 4: Bellows Falls to Brattleboro- Distance: 25 miles. Spend 1 or more nights.

photoOn your final stage back to Brattleboro, you'll follow the course of the mighty Connecticut River, which forms the border between Vermont and New Hampshire. The route is rich in diversity, alternating between historic villages, farms, and dense forests. The terrain is gently rolling for the most part, with occasional rises providing beautiful views of the mountains just across the river.

About half-way through the route you arrive in the quintessentially Vermont village of Putney, known as a Mecca for arts and crafts, and a wonderful opportunity to break, refuel, and take a stroll.

In Brattleboro, you'll have a final opportunity to shop for keepsakes made by Vermont artisans and enjoy fine dining and entertainment before heading home.

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