Vermont > Woodstock Road Weekend Bike Tour


 August 9-11, 2019 

Woodstock, Vermont, is known as one of the most scenic small towns in the U.S., and here you can experience all the charm of the region and stay in a chic bed and breakfast, too. Join us for gorgeous rides and delicious local treats in one of our favorite areas.

This tour packs so much scenery and so many fun routes into one weekend! You have options to visit beautiful farms, including one featured in several TV spots. Spin through a National Historic Park, past lovely rivers and over a famous gorge. Your efforts earn you some delicious food and drink. Taste craft beers and the famous Vermont maple, apple and dairy products. And maybe bring home some souvenirs or antiques.

Each night, your hosts welcome you to a cozy room full of special decorating touches. Plus, you are treated to a fabulous homemade breakfast you’ll love. Gather your friends and make a weekend to remember.

Woodstock Road Weekend


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

DAY ONE  |  Distance: 12 to 20 miles |  Terrain: Easier to Intermediate |  Hotel: The Woodstocker B&B
Settle into your room at the trendy Woodstocker B&B. Each room is unique, has a king bed and is decorated with a special theme. Then get ready to meet your group for a short shakeout ride. Cycle through the Marsh-Billings-Rockefeller National Historical Park and along Barnard Brook, enjoying wide shoulders and farm country as we cross the Appalachian Trail. There’s an option for more climbing with a bonus stop at Silver Lake to have a snack at the restored 187-year-old Barnard General Store. Then return to Woodstock for our welcome dinner.

DAY TWO  |  Distance: 25 or 38 miles  |  Terrain: Easier to Intermediate |  Hotel: The Woodstocker B&B
Cycle through South Woodstock’s lovely horse country, around dramatic Mount Ascutney and on to Harpoon Brewery in Windsor. Along the way, stop by famously scenic Jenne Farm. Have lunch and a beer tasting at the Harpoon Brewery. The day ends with an optional ride back to Woodstock, crossing through the stunning Taftsville wooden covered bridge.

DAY THREE | Distance: 10, 20 or 30 miles |  Terrain: Easier or Intermediate
Take the iconic “covered bridges ride,” with an optional route to Pomfret and the beautiful farm roads down to the White River and on to Quechee. Or enjoy an easier ride along the Ottaquechee River to Quechee Gorge State Park. Then return along the river and enjoy a final celebratory lunch in Woodstock.

Woodstock Road Weekend


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

reserveAugust 9-11, 2019: $995
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: $300

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 this relaxing and romantic bed and breakfast in the heart of the historic village of Woodstock, Vermont. Each chic room is specially decorated with a unique theme, and each features the luxury of a king-sized bed and other amenities.


What’s Included

2 nights of lodging; 2 breakfasts and 2 dinners; free use of bicycle and helmet; detailed maps and itineraries; experienced guides; full van support; cycling at your own pace along routes that we have carefully selected and continually improve.


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.