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

Vermont Cycling Tour Itineraries

Brattleboro, VT - Greenfield, MA 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, VT and Greenfield, MA. 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 8 cycling day-trips ranging from 11 to 31 miles.


Southeastern Vermont's lovely and historic Windham County, and large portions of Massachusetts' Franklin and Hampshire counties. All rides begin and end in Brattleboro or Greenfield, MA. 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, Vermont 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.

Change of Hubs - Cycle 28 miles from Brattleboro to Greenfield

photoYour route to Greenfield leaves Brattleboro to the south, passing old family farms in Guilford that soon give way to the deep woods bordering Weatherhead Hollow. Just beyond Weatherhead Hollow Pond, you'll take a tiny road shaded beneath the forest canopy along which flows a rushing creek. It is here that you enter Massachusetts and the village of Bernardston.

Just beyond Bernardston your route follows the Franklin County Bikeway network though beautiful rolling country interspersed with farms, woods, and villages. Before you reach Greenfield, you pass through her sister town of Turners Falls, with its historic downtown and canalside bike path. Just before reaching Greenfield your route takes you across a bikes-only former railroad bridge across the wide Connecticut River.

Named for the beautiful green and fertile valley it occupies, Greenfield is a classic New England town, with a small-town atmosphere but big-town amenities. Incorporated in 1753, Greenfield has a long history and is the seat of Franklin County. Accommodation options for your stay in Greenfield include two bed & breakfasts and 3 hotels. View Greenfield's accommodation options.

Hub 2: Greenfield, Massachusetts

photoThe Greenfield / Turners Falls area features many historic sights and nearby  recreational opportunities.

Both towns offer detailed self-guided walking tours of their historic downtown areas. (These walking tours are included in your tour package.)

The Village of Turners Falls was developed as a planned industrial community in the late 1800's. Downtown Turners Falls is a registered National Historic District featuring distinctive 19th century architecture. The village is home to a number of working artist studios, the Shea Theatre, the Hallmark Museum of Contemporary Photography, and the Great Falls Discovery Center, which interprets the Connecticut River Watershed's rich natural, cultural, and industrial history.

Finally, a bikes-only path leads to the Greenfield Swimming and Recreational Area, with 2 river beaches, a bath house, concession stand, and picnic areas.

Historic Deerfield & Shelburne Falls - 29 miles

Shortly after your departure from Greenfield you'll arrive in the historic Deerfield Village, which features 11 museum houses with trained guides and world-class antiques in the heart of the 330-year old village. Settled in 1669, Deerfield was the most important town in western Massachusetts during Colonial times. Following Deerfield you'll enjoy tranquil wooded cycling along the county's designated bikeways en route to your next destination.

photoShelburne Falls is a gem. Beautifully set amidst the mountains along the Deerfield River, its look harkens back to a simpler time when Main Street provided all the necessities of life. Here you will find a living Main Street (actually called Bridge Street), but you will also experience history and culture.

The village has become a Mecca for artists, whose studios and shops you will find dotting the village streets. You'll see the remnants of 18th and 19th century factories along the river, once having taken full advantage of the the energy of Salmon Falls. Beneath the falls you'll see evidence of the retreat of the glaciers following the last Ice Age; the largest glacial potholes in the world are here. Finally, when you live in a setting of stunning beauty and the trolley is closed, what do you do with the old trolley bridge? Shelburne Falls created the Bridge of Flowers, transforming the 1908 400-foot, five-arch concrete trolley bridge into a veritable arboretum above the water. Now that's class!

Connecticut River Valley - 25 miles

photoThis fairly easy ride lets you get a feel for both shores of the Connecticut River, which bisects the twin towns of Greenfield and Turners Falls. The western shore is primarily agricultural, with farms stretching along the fertile floodplain. The route is rolling nonetheless, as this side of the river is peppered with hills that appear to rise as if out of nowhere.

At the historic village of Sunderland you reverse direction and take it the eastern shore, which is thickly forested, thinly populated, and with just enough roll to make cycling a total pleasure. You'll enjoy lovely views of the river and wonderfully bucolic cycling.

Rivers & Vistas - 31 miles

photoThe most challenging of the Greenfield spokes, this wonderful ride features stunning river views, long vistas, and dramatic descents, your reward for enduring the tough climbs. During much of the ride you'll follow the course of the Connecticut and the Millers Rivers.

From Greenfield you'll cycle bike paths, first along the Turners Falls' Connecticut River Canal and then along the Connecticut River itself through Tuners Falls' pretty riverfront park. A few miles from the village you plunge back down to the Connecticut River with a great view of the French King Bridge (pictured above) and more tranquil cycling along the forested banks of the river.

Next you'll follow the course of the Millers River, a wonderful, fast-moving river that powered many factories in days gone by. As you cross to the south bank, which rises abruptly from the river, you'll climb to new heights for unobstructed views of this beautiful area. Then you'll descend to the village of Millers Falls, one of Massachusetts's 19th industrial powerhouses. Your short ride back to Greenfield takes you through protected woodlands and between the lovely Green Pond and Lake Pleasant.

Return to Brattleboro - 27 miles

Your return ride to Brattleboro takes a completely different route from that of your ride from Brattleboro to Greenfield. The highlight of this ride comes once you've arrived back in Vermont. You'll cycle a particularly scenic stretch of the Connecticut River past dairy farms and scattered woodland, and you'll enjoy awesome views of the river and the mountains on the New Hampshire bank.

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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