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

Vermont Cycling Tour Itineraries

The Pioneer Valley Meets the Mohawk Trail Tour

The Beauty, History & Culture of Western Massachusetts

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.


This itinerary is generally much less strenuous than those that are set solely in Vermont. The terrain is mostly easy to moderately challenging, with lots of gently rolling areas. However, there are stretches of the ride that will test your climbing mettle.


120 miles in 4 stages plus miles of optional cycling. Average of 30 miles per day.


Southeastern Vermont's lovely and historic Windham County, and large portions of Massachusetts' Franklin and Hampshire counties. Located just south of Vermont's Green Mountains, the Berkshire Foothills in west-central Massachusetts feature the same splendid scenery, only with broader valleys. See Getting to Brattleboro for transportation options to the tour's starting point.


  • Overnight destinations: Brattleboro, VT; Greenfield, MA; Northampton, MA; & Shelburne Falls, MA
  • Gorgeous scenery
  • Mostly easy-to-moderate cycling along river valleys
  • Visits to historic New England cultural and art centers. Both Brattleboro and Shelburne Falls have been designated as one of the 100 Best Small Art Towns in America.
  • Opportunities to supplement your cycling with visits to museums and artisan galleries; or with hiking and swimming, or canoeing.

*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 Greenfield, MA - Distance: 28 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 Greenfield, MA.

Today's route 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.

Optional Free Day(s) in the Greenfield / Turners Falls Area

photoWe encourage you to spend at least two nights in the Greenfield / Turners Falls area to take advantage of the many historic sights and recreational opportunities nearby.

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.

Just a short bike ride away is 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.

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

Stage 2: Cycle from Greenfield, MA to Northampton, MA - Distance: 30 miles. Spend 1 or more nights.

photoToday's route continues to take advantage of quiet, scenic valley roads that combine bucolic beauty with the charm of historic villages like Montague and Leverett. Then it's on to Amherst, an idyllic college town whose 5 area colleges and universities make it a lively cultural center, complete with museums and lots of youthful energy.

In Amherst, you'll take the Norwottuck Bike Trail, to the day's final destination, Northampton. This popular rail trail connects the towns of Amherst and Northampton via a paved, shaded path with clearly marked exits for the cross streets.

Northampton is another college town, but is much more. It has a great historic downtown district, beautiful parks, museums, and bike paths that connect virtually every part of the town. Bordering the Connecticut River and with the backdrop of the Mount Holyoke mountain range, Northampton boasts a gorgeous setting.

Accommodation options for your stay in the Northampton area include two B&Bs, 1 elegant old-style hotel, and a variety of hotel / motel options. View Northampton's accommodation options.

Optional Free Day(s) in the Northampton Area with Optional Cycling.

photoThere is much to do in this area, particularly for those interested in history and culture.

Museums in the area include the UMass University Museum of Contemporary Art, the Emily Dickenson Museum and Homestead, the Amherst College Museum of Natural History, the National Yiddish Book Center, the Eric Carle Museum of Picture Book Art, and the Smith College Museum of Art.

For a different kind of culture, you can visit the Hadley Farm Museum.

Downtown Northampton features an abundance of charm, from its striking architecture and friendly inhabitants to its unique mom 'n pop stores that dot Main Street. It also contains several top performance venues, including the Iron Horse Music Hall, Calvin Theatre and Performing Arts Center, and Pearl Street Nightclub.  You'll want to take in at least some of the many artisan galleries, which range from jewelry design to Tibetan hand-crafted items to silver and stainless steel pieces.

Northampton (and Amherst) also feature many outstanding locally-owned, independent restaurants, whose chefs take great pride in serving the best in contemporary, traditional, ethnic, and comfort food. many of them participate in the farm-to-table movement, utilizing the freshest local meat, eggs, and produce from among 35 area farms. The tremendous variety of cuisines includes Moroccan, Argentine, Indian, Tibetan, Japanese, Thai, Italian, and vegetarian.

You'll also want to spend some time getting further acquainted with the scenic beauty of the area. Northampton's amazing network of bike paths makes this easy. Take the Northampton Bikeway west to explore beautiful 150-acre Look Park and the charming village of Florence. Take the Manhan Bike Trail south to visit the Connecticut River's Oxbow, for close-up views of Mount Tom, and to explore the neighboring villages of Easthampton and Southampton. And take the Norwottuck Bike Trail to reach Amherst and the wetland conservation areas just east of Amherst. There are walking trails off the bike paths that provide a wonderful opportunity to really get to know the area.

For those who wish to test their climbing metal, you can make a loop through the Mount Holyoke Ridge, where gorgeous views and a variety of hiking trails beckon in the 400-acre Skinner State Park.

Stage 3: Cycle from Northampton, MA to Shelburne Falls, MA - Distance: 27 miles. Spend 1 or more nights.

photoToday's route feels more remote than those of the previous days. After leaving Northampton via the Northampton Bikeway, you enter into predominantly wooded areas that parallel rivers and reservoirs. The scenery is understatedly stunning. With the exception of the historic village of Conway, your route is all about wonderful cycling on quiet roads.

Shelburne 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!

Accommodation options in Shelburne Falls include two B&Bs. View Shelburne Falls' accommodation options.

Stage 4: Cycle from Shelburne Falls, MA to Brattleboro, VT - Distance: 35 miles. Spend 1 or more nights.

photoToday's route is nothing less than stunning. From your departure from Shelburne Falls -- along the historic Mohawk Trail -- to your arrival back in Greenfield, you'll enjoy stunning views of the forested mountains -- your reward for what was largely a gradual climb from Northampton to Shelburne Falls.

After a final ride through Greenfield and Turners Falls, you'll return to tranquil, gently rolling farmland and woods as you bid goodbye to Massachusetts' Pioneer Valley.

Finally, you're back in Vermont for a final scenic ride through Connecticut River-side farmland with awesome views of the river and the mountains on the opposite 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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