Diverse Directions

Self-Guided Bicycle Tours in Vermont, New Hampshire & Massachusetts

Vermont Tour Itineraries - Overview

Circuit Tour Itineraries

Diverse Directions currently offers 5 circuit tour itineraries in southern Vermont, west-central Massachusetts, and small portions of western New Hampshire. Each circuit tour begins and ends in Brattleboro, Vermont's southern gateway. Some are 3 stages and some are 4 stages. The number of stages represents the number of required cycling days as well as the number of unique overnight destinations. However, you are 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.

For a detailed description of each circuit tour itinerary, please click on the tour name below:

The differences between our circuit tour itineraries include:

  • Degree of Difficulty: The Bridges of Windham County tour is the most challenging of all the itineraries, with many long and, in some cases, steep climbs which some leisure cyclists may not enjoy. Each of the other itineraries is much less challenging and are ideal for leisure-time cyclists and families. That being said, any cycling in this region requires a relative degree of physical fitness. Please note additionally that the additional stage of the 4-stage Historic River Valleys tour involves a very long, though not terribly steep climb.

  • Focus: Our Bridges of Windham County tour appeals to cyclists who seek to acquaint themselves with the area through its heritage as represented by the monuments to history that are its covered bridges and villages. Our Vermont Outdoor Adventurist tour appeals to cyclists who wish to immerse themselves in the natural beauty of the area by hiking its mountains and swimming and canoeing / kayaking its rivers and waterways. Finally, our Historic River Valleys tours and the Berkshires Foothills tour appeal to cyclists who wish to see and experience a larger slice of southern New England in a short amount of time.

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. There is only one required cycling day for Hub & Spoke tours --  the day that you move from your first hub to your second hub.

Diverse Directions currently offers one Hub & Spoke itinerary, the hubs being Brattleboro and Bellows Falls, Vermont. From each hub we provide 5 roundtrip cycling excursions, or spokes. Most of these spokes are easy to moderately challenging, though we do provide some challenging options. In addition to Windham County, VT, the spokes include cycling in neighboring counties of New Hampshire and Massachusetts.

You are 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.

See Brattleboro - Bellows Falls Hub & Spoke Tour for a detailed description of this tour itinerary.