Classic Vermont Bike Tour
The Heart of New England
Vermont has been called the Ireland of America for its small villages, lush green rolling hills, and relaxed way of life. You’ll enjoy moderate cycling (“Vermont Ain’t Flat” is what the t-shirts say) between the foot of the Green Mountains and the shore of Lake Champlain. Start and end in the Art and Soul village of Vermont, historic Brandon, freshened up by a total restoration and reconstruction of its vibrant downtown. Your other base this week is Middlebury, a cosmopolitan village filled with all the culture and commerce brought by hosting a top-tier liberal arts college. In between, you’ll pedal up and coast down rolling hills through apple orchards, dairy farms, hayfields, and covered bridges, with an end-of-tour change of pace treat biking around a thousand-acre lake in the Green Mountain National Forest. A vintage state park beckons you for a refreshing swim.
Tour Essence
- Arrival day ride through three covered bridges of the Marble Valley with optional visit to the Vermont Marble Museum or New England Maple Museum (both ship)
- Tuesday (optional), ferry across Lake Champlain to explore historic Fort Ticonderoga
- A tasting trail of several micro-breweries and artisan wineries either en-route or within a stone’s throw
- Middlebury College with its spectacular campus of limestone buildings and views of the Adirondack Mountains of New York and Green Mountains of Vermont
- Branbury State Park and the award-winning Moosalamoo National Recreation Area: take a swim, paddle a kayak or canoe, or enjoy a hike to the Falls of Lana waterfall
What to Expect
Start Location
Brandon, VTEnd Location
Brandon, VTMileage
Average Daily: 31 / 35.6 miles Total: 155 / 178 milesElevation
Average Daily: 1.700 / 2.135 feet


Once you have a trip confirmed, we will feed you a steady diet of additional pre-departure information that includes: How to train, prepare, pack and all the wonderful, inspirational and practical things you want and need to know before you go! Our Travel Advisors will be available to help plan your pre- and post-tour travel.
- All accommodations
- 4 breakfasts
- 3 dinners
- Ciclismo Guides
- Van Support
- Snacks
- Cultural visits and walks
- Ciclismo Classico Jersey & Water bottle
- Ciclismo Goodie Bag
- Welcome cocktail
- All accommodations
- 4 breakfasts
- 3 dinners
- A tasting trail of several micro-breweries and artisan wineries either en-route or within a stone’s throw
- Middlebury College with its spectacular campus of limestone buildings and views of the Adirondack Mountains of New York and Green Mountains of Vermont
- Branbury State Park and the award-winning Moosalamoo National Recreation Area: take a swim, paddle a kayak or canoe, or enjoy a hike to the Falls of Lana waterfall
2021
Start Location
Brandon, VTFly Into
Burlington, VTEnd Location
Brandon, VTFly Out Of
Burlington, VTThree Covered Bridges of the Marble Valley
Meals Provided
DinnerAverage Mileage
milesMeals Provided
DinnerAccommodations
The Brandon Inn
Presiding on the town green, an inn has stood here since 1786. The present gracious Dutch Colonial building was erected in 1892 and is one of 250 buildings in the center of Brandon Village listed on the National Register of Historic Places. A generous breakfast in the sunny wicker room is a splendid start to your days of cycling from the inn.
The Apple Orchards and Dairy Farms
Meals Provided
Breakfast, DinnerAverage Mileage
milesMeals Provided
Breakfast, DinnerAccommodations
The Brandon Inn
Presiding on the town green, an inn has stood here since 1786. The present gracious Dutch Colonial building was erected in 1892 and is one of 250 buildings in the center of Brandon Village listed on the National Register of Historic Places. A generous breakfast in the sunny wicker room is a splendid start to your days of cycling from the inn.
The Land of Milk and Honey
Meals Provided
BreakfastAverage Mileage
milesMeals Provided
BreakfastAccommodations
Swift House Inn
The Swift House is a former Vermont governor’s restored family manse and associated houses that have been tastefully restored with guest comfort in mind. Jessica Stewart Swift, the governor’s daughter, was born in the main house and lived to the age of 110, experiencing both the US Centennial and Bicentennial celebrations on Middlebury Green. She is the oldest person ever born in Vermont. The inn’s restaurant, Middlebury’s top-rated fine dining, is named for her. You’ll enjoy breakfasts there both mornings and dinner the final night of your stay at Swift House.
The Otter Creek Meanderings
Meals Provided
Breakfast, DinnerAverage Mileage
milesMeals Provided
Breakfast, DinnerAccommodations
Swift House Inn
The Swift House is a former Vermont governor’s restored family manse and associated houses that have been tastefully restored with guest comfort in mind. Jessica Stewart Swift, the governor’s daughter, was born in the main house and lived to the age of 110, experiencing both the US Centennial and Bicentennial celebrations on Middlebury Green. She is the oldest person ever born in Vermont. The inn’s restaurant, Middlebury’s top-rated fine dining, is named for her. You’ll enjoy breakfasts there both mornings and dinner the final night of your stay at Swift House.