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

Vermont Tour Itineraries - At A Glance

The table below provides an overview of each Diverse Directions tour itinerary offered in Vermont, New Hampshire, and Massachusetts.

  • Click the tour itinerary's name to view detailed information for a particular tour, including its daily itinerary, approximate route map, photo slideshow, and order form.
  • Prices on this page are in US dollars and are per person. The tour package price does not include bike rental or accommodations. Bike rentals are available for $25 per bike per day and are subject to 6% Vermont sales tax. See Tour Prices for additional pricing information.
Vermont Tour Itineraries Overnight Destinations Tour Format Stages* Level of Difficulty Price Single Supp't
Green Mountain Vistas Brattleboro, Ludlow, Weston, & Stratton, VT Circuit 4 Moderately Challenging to Challenging $249 $125
Vermont Outdoor Adventurist Brattleboro, Grafton, Jamaica, & Bellows Falls, VT Circuit 4 Moderately Challenging $249 $125
The Pioneer Valley Meets the Mohawk Trail Brattleboro, VT; Greenfield, MA; Northampton, MA; & Shelburne Falls, MA Circuit 4 Easy to Moderately Challenging $249 $125
Historic River Valleys 4-Stage Tour Brattleboro, Bellow Falls, Grafton, & Chester, VT Circuit 4 Easy to Challenging $249 $125
Historic River Valleys 3-Stage Tour with Chester Brattleboro, Bellow Falls, & Chester, VT Circuit 3 Easy to Moderately Challenging $199 $95
Historic River Valleys 3-Stage Tour with Grafton Brattleboro, Bellow Falls, & Grafton, VT Circuit 3 Easy to Moderately Challenging $199 $95
The Bridges of Windham County Brattleboro, Jamaica, & Wilmington, VT Circuit 3 Very Challenging $199 $95
Brattleboro - Bellows Falls Hub & Spoke Brattleboro & Bellow Falls, VT Hub & Spoke N/A Moderately Challenging to Very Challenging $149 $0
Brattleboro - Greenfield Hub & Spoke Brattleboro, VT & Greenfield, MA Hub & Spoke N/A Moderately Challenging to Very Challenging $149 $0

*A "stage" is defined as a day in which tour support services are provided and cycling is required from one hotel or B&B to the next. Of course, you may spend as many days as you like at any of your tour's overnight destinations.

Circuit Tour Itineraries

Diverse Directions offers 7 circuit tour itineraries in southern Vermont, west-central Massachusetts, and small portions of western New Hampshire. Each itinerary is comprised of 3 or 4 stages. The number of stages represents the number of required cycling days as well as the number of unique overnight destinations. You're free to spend as many days as you like at each of the overnight destinations. We provide day-trip cycling options and suggested activities to enhance your appreciation of each of the overnight destinations. All circuit tour itineraries include GPS navigation files at no additional charge.

Hub & Spoke Tour Itineraries

Diverse Directions' 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. With our Hub & Spoke tours, you stay in two different base locations (hubs), from which you cycle roundtrip day trip rides (spokes.) Since you are not changing hotels on most days, the choice is always yours as to whether you cycle or enjoy other activities.

You're free to spend as many days as you like cycling the day-trip rides from each base. At the end of your tour, Diverse Directions will transfer you and your luggage back to Brattleboro to reunite you with your vehicle.