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

Vermont Cycling Tour Itineraries

The Green Mountain Vistas 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.


Moderately challenging to very challenging. With the exception of a very challenging 2-mile climb in stage 2 with an average grade of 6% -- and the stage 3 climb to the summit of Stratton Mountain, which is completely optional -- the cycling of this itinerary is generally easy to moderately challenging. If you're in descent shape and exercise / cycle regularly you should not be deterred from making this exceptionally beautiful tour.


109 miles in 4 stages. Average of 27 miles per day.

Shuttle to Windsor

Because this tour does not begin and end in the same location Diverse Directions will shuttle you from Brattleboro (where you'll leave your car for the tour's duration) to the tour's starting point in Windsor immediately following your orientation.


The itinerary begins in historic Windsor, the birthplace of Vermont. The route proceeds west into the Green Mountains and then south along the edge of the Green Mountain National Forest. The final stage takes you through the lovely West River Valley back to Brattleboro. See Getting to Brattleboro for transportation options to the tour's starting point.


  • Overnight destinations: Brattleboro, Ludlow, Weston, & Stratton.
  • Gorgeous mountain scenery as seen from quiet, tiny roads.
  • A number of covered bridges, including the world's longest dual-span.
  • Visits to two popular Vermont ski resort areas, including an overnight stay at Stratton Mountain resort.
  • The beautiful, quintessentially Vermont villages of Windsor, Ludlow, Weston, Jamaica, and Newfane.
  • Rushing mountain rivers and forests.
  • Opportunities to supplement your cycling with visits to museums and artisan galleries or with hiking and swimming.
  • Brattleboro, southern Vermont's lively arts and cultural center.

*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 Windsor to Ludlow - Distance: 27.5 miles. Spend 1 or more nights.

Following breakfast you'll attend a brief orientation at your hotel, test ride your bicycle, and then we'll shuttle you to the tour's starting point in historic Windsor, the birthplace of Vermont.

It was in Windsor in 1777 that the Republic of Vermont was born. Having battled New York and Massachusetts for decades in attempts to maintain sovereignty, Vermont was not prepared to join its neighbors in the newly established US. Nor was it welcome, since its sovereignty as a colony was not recognized.

photoYour tour begins at the Windsor-Cornish Bridge, the world's longest dual span covered bridge, and takes you through the town's historic district before climbing into the adjacent Green Mountain foothills.

For the first half of today's ride you'll cycle in the shadow of Mount Ascutney, the highest peak in the area, unmistakable as it rises considerably higher than any of the surrounding peaks. After about 7 miles, and with most of your climbing behind you, you arrive in the tiny hamlet of Brownsville. From here you'll enjoy gorgeous, easy cycling along unpaved roads winding along forested river shores. You'll also encounter your second covered bridge.

In Perkinsville you'll begin following the course of the Black River -- rarely out of view for the remainder of today's ride -- and you'll get a glimpse of yet another covered bridge. You'll enjoy easy riverside cycling with only an occasional rise and fall in the roadway as you make your way to Cavendish and Proctorsville. As you pass through these twin villages the peak of Okemo Mountain looms larger and larger, beckoning you on to Ludlow, which sits at the base of the mountain. At 3,344 feet, Okemo is the tallest peak in this part of Vermont. Rising almost 2200 feet from the valley floor, Okemo features the largest vertical drop all of Vermont ski resorts.

photoLudlow's history dates back to the mid-19th century when it was founded a classic mill town harnessing the power of the rushing Black River. Long before the opening of Okemo ski resort in 1956 Ludlow had established itself as a thriving four-season town, exciting marketplace, and vibrant community in the heart of the spectacular Okemo Valley.

Today Ludlow boasts a concentration of delightful shops, galleries, and restaurants: a true walking town. Off-season -- that is, any time but winter -- is a great time to enjoy Ludlow's charms and Okemo's recreational opportunities, and fall foliage is truly spectacular. The primary non-winter activities are hiking and golfing. For those interested in hiking, the 5.8 mile roundtrip Healdville Trail ascends to the summit of Okemo Mountain for stupendous views of the region. The hike is fairly strenuous and takes about 4 hours to complete.

Accommodation options include both B&Bs and motels.

Stage 2: Cycle from Ludlow to Weston - Distance: 20 miles. Spend 1 or more nights.

photoToday's gorgeous ride takes you into the Green Mountains in earnest. Though you won't cycle to Okemo's summit, your ride takes you near the top of the ridge where you'll enjoy the splendid wooded scenery and sweeping vistas of the Green Mountain National Forest. Because of this challenging climb we've kept today's mileage fairly short so that you can relax and savor the experience. Your ride tops out at the tiny hamlet of Belmont, with its classic church, general store, and post office, before descending rapidly to your next destination, Weston.

With one foot firmly planted in the foothills of the Green Mountain photoNational Forest and the other in the fertile West River valley, Weston has come to exemplify Vermont at its finest. Anchored by one of the most picturesque village greens in Vermont, the entire village is listed on the National Register of Historic Places. With hills rising prominently on all sides and a crystal clear brook running through the center of town, Weston is a veritable looking glass back to 1799, the year the town was incorporated. Historic homes and antique shops, bountiful general store, museums, galleries, gardens, inns, artists, arborists, and shops of all shapes and sizes grace the village's main street and the roads that needle into the hills in every direction. Other attractions include the original Vermont Country Store, source of Vermont products; the renowned Weston Playhouse, Vermont's oldest professional theatre company: and the famous Weston Priory, a Benedictine monastery and one of the last of its kind. Accommodation options include five B&Bs.

Stage 3: Cycle from Weston to Stratton - Distance: 22 - 28 miles (depending on the location of your accommodations.) Spend 1 or more nights.

photoFrom Weston your route begins to follow the West River, the course of which you'll rarely leave for the remainder of the tour. At Londonderry, your next village, you'll begin a long beautiful descent along the west bank of this river. In South Londonderry you'll continue your riverside cycling, but now on the West River rail trail.

When the rail trail ends you'll return to quiet country roads that rise and fall with the rolling terrain of the foothills as you make your way to Bondville, the tiny village at the base of Stratton Mountain. From this point you have options. You may (1) settle into accommodations in Bondville, (2) make the 3.5-mile climb to Stratton's summit, or (3) permit Diverse Directions to shuttle you and your bike to the 3,875 foot (1,181 meter) summit. The ascent is very challenging, though the grade does ease slightly every now and again.

photoAt the summit you'll enjoy a stay in the attractive resort village of Stratton, seemingly atop the world. Established in 1961, Stratton rapidly expanded into one of Vermont's largest ski areas. In addition to the resort's shops and restaurants, you'll probably want to take advantage of the many hiking trails for endless views from southern Vermont's highest peak. Or you may take the high-speed gondola or rent an all-terrain-vehicle for a more restful trip to the summit. Or perhaps you would prefer to simply pamper yourself with a massage at the day spa. View Stratton's accommodation options.

Stage 4: Cycle from Stratton to Brattleboro - Distance: 36 miles. Spend 1 or more nights.

photoYour final cycling day begins with  a descent, the likes of which you may have never experienced. Your first 8 miles are down, down, down. All you have to do is watch your speed -- no pedaling required -- and drink in the beauty of the woods and the rushing Ball Mountain Brook.

At the end of your race to the bottom is the lovely village of Jamaica, a quintessentially Vermont village with a number of artisan shops and a coffee shop and grocer for some refreshment. In Jamaica you rejoin the West River as you continue your descent, though less dramatic now, into the beautiful West River Valley.

After cycling across the Townshend Dam, you'll have the opportunity to stop for a break (or a dip) at Townshend Lake, the reservoir created from the damming of the West River. Just a bit further along you'll see Vermont's longest covered bridge, the Scott Covered Bridge, now closed to vehicular traffic, as you make your way down quiet dirt roads adjacent to the river.

photoAfter one of the few climbs on today's ride you'll enter Newfane, the gem of the West River Valley and considered the loveliest of Windham County's so-called 18th Century "White Villages." Newfane is strikingly Vermont, with pretty white frame houses and churches, as well as its Federal-style courthouse towering above the village green.

Just south of Newfane you'll pass the West Dummerston Covered Bridge, the longest covered bridge in Vermont that's still in use. Adjacent to the bridge is a popular West River swimming hole. Perhaps you'll want to have your swim suit handy. After all, it's all downhill from here to Brattleboro.

In Brattleboro you'll return your bicycle, shop for keepsakes made by Vermont artisans and enjoy a final evening of fine dining and entertainment before heading home.

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