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

Vermont Cycling Tour Itineraries

Historic River Valleys 3-Stage Tour with Chester

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

3-stage circuit tour requires a minimum of 3 days / 4 nights. Spend as many days as you like in overnight destination.


This is the least challenging of our Vermont circuit tours. The terrain is mostly easy to moderately challenging. However, there are stretches of the ride that will test your climbing mettle.


88 miles in 3 stages plus miles of optional cycling. Average of 29 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, & Bellow Falls
  • Gorgeous scenery
  • Mostly easy-to-moderate cycling along river valleys
  • Visits to quintessential Vermont and New Hampshire villages, including Grafton, Chester, Walpole (NH) and Newfane, among New England's most beautiful
  • Opportunities to supplement your cycling with hiking, swimming, or canoeing
  • Historic covered bridges

*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, VT to Bellows Falls, VT - Distance: 27 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 Bellows Falls.

Today's route follows the mighty Connecticut River, which forms the border between Vermont and New Hampshire. Though cycling in the fertile, orchard-studded valley carved by the river, the terrain is gently rolling, with occasional rises providing beautiful views of the mountains just across the river. You arrive shortly in the quintessentially Vermont village of Putney, known as a Mecca for arts and crafts, and a wonderful opportunity to break and refuel.

Beyond Putney, your route takes you down to the riverside for wooded cycling on a quiet dirt road before reaching Westminster. In Westminster you cross the river to the New Hampshire side for the day's final riverside stretch. Just ahead, the mountains begin to close in on you, creating Bellows Falls' dramatic setting. Crossing back into Vermont, you reach the day's final destination, Bellows Falls.

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. If you prefer to stay in a smaller village, you also have the option of staying at one of two B&Bs in nearby Saxtons River, VT. 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.

In addition to these cycling options, you can make the short, scenic ride along the Saxtons River to the quaint village of Saxtons River. Or you can take a break from cycling altogether and spend the day looking at Indian petro graphs by the river, browsing in the local shops, or strolling the streets to become more familiar with the charms of Bellows Falls.

Stage 2: Cycle from Bellows Falls to Chester, VT - Distance: 27 miles. Spend 1 or more nights.

photoLeaving the relative bustle of Bellows Falls you quickly return to  quiet, wooded cycling along the Vermont side of the Connecticut River. Here the river cuts right through the more rugged landscape, providing occasional vistas of the narrow river valley. Bidding adieu to the Connecticut, you then begin a gradual westward ascent on a paved rail trail that parallels the Black River to Springfield, VT. There you'll have an opportunity to have lunch and enjoy strolling the picturesque streets of its nicely preserved downtown. Like Bellows Falls, Springfield was also a manufacturing powerhouse in the 19th century, and you can still see its Industrial Revolution era factories that once harnessed the river's power. Beyond Springfield your route takes a long, challenging climb before plunging down to the Williams River, the course of which you will follow via tranquil, thickly forested dirt roads the remainder of the way to Chester.

Chester is a village full of charm and good-natured Vermonters looking to share their portion of paradise with you. You'll definitely want to spend some time exploring Chester's artisan and retail shops, marveling at the grand Victorian homes, and perhaps swing by Chester's "Stone House Village," named for the pre-Civil War houses constructed from locally quarried stone. Accommodation options for your stay in Chester include one historic inn, six B&Bs, and one economy motel. View Chester's accommodation options.

Optional Free Day(s) in Chester

With its quaint shops, cafes, and beautiful setting, it would be a shame not to spend at least one day relaxing and becoming better acquainted with this charming quintessentially Vermont village.

Stage 3: Cycle from Chester, VT to Brattleboro, VT - Distance: 34 miles. Spend 1 or more nights.

photoYour final cycling stage is one of exceptional beauty along quiet back roads. After leaving Chester, you return to the shaded canopy of the forest for a relaxing, rolling, and gorgeous ride into Grafton. Grafton is one of Vermont's most beautiful villages and is like a trip back to a simpler time. The restoration of its historic structures is magnificent, as is its setting.

From Grafton most of your route is downhill, so you'll have nothing to distract you from the picturesque farms and maple sugaring shacks you'll pass as  you follow the south branch of the Saxtons River to the pretty village of Townshend, your introduction to the beautiful West River Valley. Then it's on to 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.

Beyond Newfane, your route follows the West River, where you have a number of opportunities to take a dip with the locals in one of several pristine swimming holes. At the West Dummerston Covered Bridge, Vermont's longest covered bridge still open to traffic, you have the option of continuing your flat route back to Brattleboro along the West River, or taking an exceptionally beautiful, but more challenging ride through the mountains for some incredible vistas of the West River Valley.

In Brattleboro, you'll have a final opportunity to shop for keepsakes made by Vermont artisans and enjoy at least one more evening of fine dining before heading home.

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