Vermont > Woodstock Gravel Weekend – NEW! 

3-DAY / 2-NIGHT BIKE TOUR – $795 
October 4-6, 2019

On this new tour we offer you a chance to experience the thrill of rides on the dirt/gravel roads that crisscross the region around Woodstock, Vermont. This is a more informal tour than most, designed especially for those not afraid to get a bit muddy. You stay in a casual and comfortable inn at the edge of one of the most scenic and beloved towns in the U.S.

Each day, you explore quiet dirt roads, known fondly in biking circles as “gravel.” See what the buzz is about when you meet the challenging climbs and ramble down the hills and valleys around this gorgeous region. The quiet roads here are perfect to test your legs and stamina … and get the feeling of accomplishment of a day well spent outdoors climbing ridges and zooming down hills.

And then you feast on delicious meals that feature locally sourced ingredients like Vermont apples, maple syrup, cheese, ice cream and other farm-fresh treats. Grab some friends and join us for an adventure on these outstanding gravel roads.

A limited number of e-bikes are available on our regular tours, but for an e-bike group experience, join us for our new ALL e-bike tour on the Woodstock Gravel route on Oct. 4-6, 2019.

Woodstock Gravel Weekend


Enjoy three spectacular GRAVEL rides in and around the town of Woodstock, Vermont.

DAY ONE | Distance: 8-15 miles  |  Terrain: Intermediate | Hotel: The Shire
Settle into your room at The Shire hotel and enjoy the backyard views along the Ottaquechee River. Our Friday afternoon ride takes you through the Marsh-Billings-Rockefeller National Historical Park and up toward Pomfret, where you head onto gravel and your first extended climb. Top out on Cloudland Road, for a beautiful run past the scenic Sleepy Hollow Farm and back down to Woodstock.

DAY TWO  |  Distance: 24-45 miles  |  Terrain: Intermediate to Advanced |  Hotel:  The Shire
Spend Saturday enjoying the spectacular array of dirt and gravel roads to the north of Woodstock, beginning with a ride up Cloudland Road into Pomfret. The hills of Pomfret mix in climbing and long descents as you dip down into Royalton for a delicious lunch at the Worthy Burger, a local icon. Climbing back out of the White River valley, you’ll have a snack stop and an option to swim in Silver Lake in Barnard. Don’t miss a snack or milkshake at the 187-year-old restored Barnard General Store. Take one final descent back to Woodstock with an optional gravel extension and climb, and that ends a full day of Vermont gravel!

DAY THREE | Distance: 20 miles |  Terrain: Intermediate to Advanced
Today’s ride explores the gravel roads south of Woodstock. Leaving town on paved roads, you quickly transition to gravel and explore the back roads of Woodstock, Hartland and Reading. Stop for a quick coffee at the South Woodstock Country Store, then tackle one more gravel ride with a section of class 4 road and return triumphantly to Woodstock for lunch.

Woodstock Gravel Weekend


Make your reservation with confidence. Your tour is completely 100% refundable up to 60 days of the tour date.


October 4-6, 2019: $795
Reserve with $200 deposit

Final payment due 60 days prior to your tour (personal check, Visa, MasterCard, American Express or Discover)

Single Supplement Fee for Private Room: $200 

Cancellations: If you cancel your tour reservation, your cancellation fee will be determined as follows:

  • If you cancel 60 or more days prior to the start of your tour, there is no cancellation fee.
  • If you cancel between 45 and 59 days prior to the start of your tour, you will forfeit 50% of all tour payments.
  • If you cancel between 0 and 44 days prior to the start of your tour, all tour payments will be forfeited.


Enjoy riverside accommodations and local artistic touches in this inn, which has been welcoming travelers since the 1960s. Relax on the rocking chairs on the wrap-around porch or sit by the waters of the Ottauquechee River.

What’s Included

2 nights lodging, 2 breakfasts, 2 dinners, 2 lunches, experienced leaders, van support, use of bicycle and helmet.


We are happy to provide you with a bike to use at no charge. Our bikes come equipped with a front handlebar bag, rear carrier, water bottle, mirror and flat pedals. Pedal cages and soft gel seat covers are available on request. We are also happy to put your own clipless pedals (pedals that attach to your biking shoes) and seat on your bike if you wish. Specific details and styles of bikes available in each location are indicated under each photograph below. The make of bikes provided varies by location.

A collection of photos from a variety of our Vermont tours.