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

Vermont Cycling Tour Itineraries

Brattleboro - Bellows Falls Hub & Spoke 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

Hub & Spoke tour with hubs (bases) in Brattleboro and Bellows Falls. Spend as many days at each hub as you wish.


Most of the day-trip rides feature relatively easy terrain, with some including a few long, steady climbs and/or a few short, steep climbs. See spoke descriptions below for details.


Choose any or all of 11 cycling day-trips ranging from 11 to 33 miles.


Southeastern Vermont's lovely and historic Windham County; portions of Windsor County, VT; portions of Cheshire County, New Hampshire; and portions of Franklin County, Massachusetts. All rides begin and end in Brattleboro or Bellows Falls, Vermont. See Getting to Brattleboro for transportation options to the tour's starting point.

Hub & Spoke Format

Hub & Spoke tour itineraries are designed for those who prefer to minimize changes of hotels and/or like the flexibility of being able to determine which days they cycle. You stay in two different base locations (hubs), from which you cycle roundtrip day-trip rides (spokes.) Since you're not changing hotels on most days, the choice is always yours as to whether you to cycle or enjoy other activities. There is only one required cycling day for this Hub & Spoke tour -- the day that you move from your first hub to your second hub.

Hubs & Day Ride Descriptions
Hub 1: Brattleboro photo

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.

Following breakfast on your first full day in Brattleboro, you'll attend a brief orientation at your hotel or B&B, test ride your bicycle, and then begin the first of your day trip rides, or spokes.

The Many Faces of Brattleboro - 11 miles

This ride provides an in-depth look at the diverse community of Brattleboro, from its charming downtown filled with unique shops to its towering hills and wonderful views. On this ride you will have the opportunity to:

  • photoExplore the primary downtown shopping streets;
  • See the plethora of colorful Victorian homes;
  • Climb into the hills that provide a second dimension to this waterfront town;
  • Visit the Tasha Tudor Museum and the Creamery Covered Bridge in charming West Brattleboro;
  • See the former Estey Organ factory buildings; and
  • Enjoy Brattleboro's two waterfronts.
Newfane & the West River Valley - 28 miles

This beautiful ride follows the course of the West River from its mouth in Brattleboro to the quintessentially Vermont village of Newfane, one of New England's most beautiful villages. The terrain of this ride is easy overall, with just some minor exceptions. On this ride you will have the opportunity to:

  • photoSee (and cycle) the West Dummerston Covered Bridge, Vermont's longest covered bridge still in use;
  • Visit and tour the Grafton Village Cheese Company, where an incredible variety of delicious cheeses are produced and sold;
  • Visit and tour the Saxtons River Distillery and Tasting Room, where liqueurs are produced using Vermont maple syrup;
  • Experience the village of Newfane, with its classic village green, gleaming white 19th century buildings, and numerous shops where antiques and local artisan products are sold; and
  • Enjoy the remarkable beauty of the West River Valley with opportunities to take a refreshing dip in one of the many West River swimming holes.
Dummerston & Williamsville - 26 miles

photoDummerston and Williamsville are tiny picturesque 18th century villages that continue to thrive. This challenging ride takes you first to Dummerston Center, set atop the ridge that rises between the Connecticut River and the West River Valleys. As the route continues you'll enjoy a thrilling extremely steep descent to the West Dummerston Covered Bridge and swimming area.

Following easy cycling along the West River you climb the next ridge to reach the beautiful hollow in which Williamsville sits with its covered bridge spanning the Rock River.

Putney & Thrilling Mountain Cycling - 24 miles

photoThe most challenging of the Brattleboro spokes, this ride 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 local Mecca for arts and crafts, you'll have the opportunity to visit the many artisan's shops that are established here.

Following your Putney visit the route climbs up tranquil forested slopes for a thrilling ride along rivers rushing through the woods. After passing through pretty Dummerston Center your route plunges back down to Brattleboro by way of Naulakha, Rudyard Kipling's treasured home in Vermont.

New Hampshire Rivers & Lakes - 28 miles photo

Cross the bridge from Brattleboro and you have arrived in New Hampshire. This moderately challenging ride follows the course of the Connecticut River on the New Hampshire side along a quiet road that rolls along the forested shoreline with splendid river views.

The route then turns inland to sleepy villages and one of the ride's highlights: stunning Lake Spofford, a crystal clear sea of deep blue surrounded by thickly forested hills. You'll want to bring your swimsuit for a dip at the sandy public beach. The return ride to Brattleboro features thrilling descents and gorgeous views of the Vermont mountains.

Weatherhead Hollow - 23.5 miles photo

This very bucolic ride with easy-to-moderate cycling takes you west to Brattleboro's Creamery Covered Bridge, before turning south for some wonderful cycling in the hollows between the mountain ridges south of Brattleboro. The route takes you briefly into Massachusetts by way of a shaded, unpaved road that parallels a beautiful cascading river; and then brings you back into Vermont through beautifully rolling areas mixed with forests and dairy farms. Back in Brattleboro, you will pass the uniquely designed buildings that comprise the former Estey Organ factory.

Tri-State Loop - 33 miles

Experience three New England states over the course of this fascinating 33-mile loop! On this moderately challenging ride you will see the discernable differences between these neighboring states -- in their architecture, land use, and geography. Beginning in downtown Brattleboro, you immediately cross the mighty Connecticut River into New Hampshire, where you follow the course of the river to Hinsdale, NH. There you head south through the forest to historic Northfield, Massachusetts. Then, after a stretch of dazzling green beauty, you turn north again and re-enter Vermont, hugging the left bank of the Connecticut River, with gorgeous views of the surrounding mountains and riverside. A truly remarkable ride!

Change of Hubs - Cycle 27 miles from Brattleboro to Bellows Falls

Your route to Bellows Falls follows the mighty Connecticut River northward, 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 on a quiet dirt road before reaching Westminster. In Westminster, you cross the river to the New Hampshire side and the beautiful village of Walpole, another great opportunity to take a break and enjoy a tasty treat at locally renowned Burdick's Chocolates. 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.

Hub 2: Bellows Falls photo

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.

Grafton - 25 miles with an 8-mile challenging option

photoThis beautiful ride follows the course of the Saxtons River, from Bellows Falls to Grafton, one of New England's most beautiful villages. When you reach Grafton, don't be surprised if you just want to sit for hours drinking in the beauty of its 19th century buildings and lovely setting between the surrounding mountain ridges. If you can motivate yourself into action, however, you may take advantage of the many art galleries, the local museum, Grafton's covered bridge, and the original Grafton Village Cheese Company, where a tremendous variety of cheeses are produced and sold. There is also the Grafton Ponds Outdoor Center, offering a variety of trails and activities in this pretty setting.

If you're up for more challenging cycling, you can make a strenuous 8-mile loop from downtown Grafton into the surrounding mountains, featuring stunning vistas and an awesome downhill return to the village.

On your way to Grafton or on your return ride to Bellows Falls, you also have the opportunity to visit the tiny, but charming village of Saxtons River.

Chester & the Green Mountain Turnpike - 32 miles

photoThis truly unforgettable ride takes you to Chester by way of a tranquil, shaded, unpaved road that follows the course of the Williams River. The beauty of this ride could stand alone, but in addition, this day-trip loop provides the opportunity to visit 3 historic covered bridges and the ever-so-charming village of Chester, with its elongated village green lined with 19th century Victorian buildings, and its good-natured Vermonters looking to share their portion of paradise with you. You'll definitely want to spend some time exploring Chester's many artisan and retail shops, and perhaps swing by Chester's "Stone House Village," named for the pre-Civil War houses constructed from locally quarried stone.

On your return route to Bellows Falls, you'll have the opportunity to visit the village of Saxtons River, before your final short stretch of cycling along the Saxtons River.

New Hampshire River Valleys - 26 or 29 miles

photoRich in variety, this challenging loop takes you immediately across the Connecticut River into New Hampshire, where you will cycle quiet roads through a number of quaint New Hampshire villages, separated by stretches of forests and generally following the course of a rushing stream. Before crossing back into Vermont, you will visit Charlestown, New Hampshire, with its beautifully preserved historic district. You also have the opportunity to visit a restored 18th century fort to experience the early, untamed days of the region's history.

Back in Vermont, the most challenging part of the route ensues, as the mountains practically fall to the river banks along this stretch. Of course you are rewarded for your efforts with great vistas.

Walpole, New Hampshire - 11 miles

The short ride to Walpole, NH takes you to one of the most charming villages you'll ever see. Walpole is also home to Burdick's Chocolates, a true haven for the discriminating chocoholic.

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