Bike Tour Vermont’s Famed Woodstock, Quechee and Beyond
tour-item-template-default,single,single-tour-item,postid-3568,mkd-core-1.1.1,mkdf-social-login-1.1,mkdf-tours-1.3,voyage child theme-child-ver-1.0,voyage-ver-1.3,mkdf-smooth-scroll,mkdf-smooth-page-transitions,mkdf-ajax,mkdf-grid-1300,mkdf-blog-installed,mkdf-header-standard,mkdf-no-behavior,mkdf-default-mobile-header,mkdf-sticky-up-mobile-header,mkdf-dropdown-default,mkdf-light-header,mkdf-medium-title-text,wpb-js-composer js-comp-ver-5.0.1,vc_responsive

Beguiling Woodstock, VT & Beyond Bike Tour

Beguiling Woodstock, VT & Beyond Bike Tour

per person


Woodstock VT Bike Tour

Beguiling Woodstock and Beyond
Woodstock is one of Vermont’s most beautiful towns. Settled in 1768, the town has been meticulously preserved and retains its historical and architectural integrity.  The town green is bordered by handsome Georgian, Federal and Greek Revival houses. Past residents, Laurance and Mary French Rockefeller, enhanced the town’s charm by burying power lines throughout the village and by donating their mansion and property to create Vermont’s only national park.

A Perfect Vermont Vacation
What exists today is a town both true to its past yet alive with contemporary cultural and outdoor opportunities. Upscale boutiques, fine art galleries and excellent eateries line idyllic streets. And the picturesque valleys and verdant hills surrounding Woodstock make it the ideal base from which to explore the stunning countryside. Join us!

woodstock vt photography bike tourSpecial Photography Tours
The October 2-5 and 9-12 fall foliage departures will have an added perk. An expert photographer will guide the tour and provide tips and suggestions for creatively capturing the light and the tapestries of Vermont’s magnificent landscapes while bathed in radiant fall color. In the evenings, there will be opportunities to continue the learning by sharing photos and hearing how the experts create their remarkable compositions.



Tour Highlights:

  • Discover the remarkable beauty of Woodstock, Vermont
  • Cycle some of the most beautiful terrain in Vermont
  • View the Quechee Gorge, Vermont’s deepest gorge
  • Watch master glassblowers create masterpieces at renowned Simon Pearce
  • Visit Calvin Coolidge State Park and the Coolidge Homestead
  • Visit Plymouth Cheese Factory, started by Calvin Coolidge’s father
  • Stop at Long Trail Brewery, a brewer of award-winning craft beer
  • Enjoy dinners at Woodstock’s top restaurants
  • Hike to a hilltop with panoramic views
  • Departure
    Woodstock, Vermont
  • Departure Time
    Early Afternoon
  • Return Time
    Early Afternoon
  • Include
    Hiking Tour
    Bike Tour
  • Not Included
    Active Vacation

Day 1

vermont-bike-tour_000Meet at the inn in Woodstock in the early afternoon for a welcome lunch. Then, pedal through a quiet hamlet anchored by a charming country store and one of the oldest ski areas in the country. Ride alongside gurgling streams and fields where cows or horses are pastured. A sparkling lake is the reward at the end of an invigorating climb. Watch the kids splashing in the clear water or later in the season, the mirror reflection of the red and gold trees: either way, it’s a picture perfect setting. Coast down the hill back to Woodstock and relax at the inn before dinner at one of Woodstock’s top restaurants.

Biking Mileage:  21 

Day 2

vermont-vacation-5rBike one of the most scenic cycling routes around, passing farmsteads with classic red barns and tranquil ponds. Watch for farmers cutting and baling hay and listen for the cries of hawks circling overhead. Continue to Quechee for a picnic lunch among a stand of old pines. Walk the pine-needle path to the Quechee Gorge and, if you dare, look down to the river as it cuts its way through the gorge 165 feet below. Visit Simon Pearce Glassworks and watch master glassblowers create striking glassware sold in fine shops worldwide. Follow the river back to Woodstock passing three covered bridges along the way. Enjoy dinner on your own with excellent options to choose from.

Biking Mileage: 37 with an option for additional mileage

Day 3

woodstock-vt-bike-tour-10Pedal a route of remarkable diversity encompassing manicured horse farms, stately brick mansions, handsome stone houses, remote wilderness areas and a state historic site. Visit the Calvin Coolidge State Park and Coolidge Homestead and see exactly where Coolidge was sworn in by his father in 1923 as the 30th US president. Sample the artisan cheese at the Plymouth Cheese Factory, one of the country’s oldest cheese-making operations. Coast down the hill to Long Trail Brewery to sample some of the award-winning beers at this Vermont craft brewer. Enjoy dinner together at a popular Woodstock restaurant offering exceptional creations by a talented chef. Biking Mileage: 36 or 44

Day 4

woodstock-vt-1rAfter breakfast, take an optional short hike with an outsized reward. The panoramic views from the hilltop encompass local farmland and distant ridges all the way to Killington. Spend the latter part of the morning in town perusing the shops you’ve missed or just enjoying the sights. Enjoy your last tastes of Vermont at a farewell gathering.

506-on-the-river-inn506 On the River Inn, Woodstock, VT - 3 Nights (May 26, July 23 & August 7 Departures)This fine inn set on the banks of the Ottaquechee River was recommended by Conde Nast Traveler as "The place to visit." Balconied rooms overlook the expansive lawn and the river. Inn amenities include a restaurant, bistro, country kitchen, library, game room, gift shop, and an indoor pool with sauna.

woodstock-inn-2Woodstock Inn & Resort, Woodstock, VT - 3 Nights (October 2 & 9 Departures)The Woodstock Inn epitomizes New England country elegance. A Conde Nast Traveler Gold Club member, the stately inn and beautiful grounds are ideally located adjacent to the town green, in the heart of Woodstock village. Beautiful sitting spaces and fine dining rooms are enhanced by excellent service. Luxurious rooms feature furnishings handmade by talented local artisans. Additional resort amenities include a tavern, game room, pool, spa, gift shop and afternoon tea & cookies. In addition, GFA guests may use the Athletic Club (indoor pool, hot tub, sauna, steam room, racquet sports, etc.) and participate in classes.  

2018 tours booked by December 31, 2017 will receive the 2017 price (shown)

2017/2018 Dates

October 2-5 | October 9-12 | May 25-28 | July 1-4 | July 23-26 | August 6-9 | October 1-4 | October 8-11

2017 Prices

May, July and August Departures: $1,495, October Departures: $1,895. Per person, based on double occupancy. Single Supplement: $550 ($650 October Departures)

Trip Length

4 days, 3 nights


Woodstock, VT

Daily Mileage

21-37 with longer options if desired

Cycling Level

Moderate. Moderate-Challenging with longer distance options.


Paved and dirt roads. Some long and short hills each day along with flatter stretches.

Bikes: You may bring your own bike or use one of ours. GFA bikes are high quality, lightweight, available with either drop or straight handlebars and are equipped with computer, mirror, waterbottle, handlebar bag, map case and seat pack with essentials. Special Photography Tours: The October 2-5 and 9-12 fall foliage departures will have an added perk. An expert photographer will guide the tour and provide tips and suggestions for creatively capturing the light and the tapestries of Vermont’s magnificent landscapes while bathed in radiant fall color. In the evenings, there will be opportunities to continue the learning by sharing photos and hearing how the experts create their remarkable compositions. What’s Included:
  • 3 nights accommodations in a fine Woodstock inn
  • 4 days of bicycling and walking
  • Bicycle and helmet rental
  • 3 breakfasts
  • 2 dinners
  • 2 lunches
  • Admission to Calvin Coolidge Homestead
  • Visit to one of the oldest cheese-making operations in the US
  • Brewery visit
  • 2 guides
  • Van support
  • Daily cold drinks and snacks
  • Maps and cue sheets for each day's ride
  • Tax and gratuities at inn and restaurants
  • Featherweight, high visibility, reflective vest
  • Waterbottle
  • Dedicated service throughout your worry-free tour
  • The October 2-5 & 9-12 tours include instruction as desired from an expert photographer
Note: This bike tour runs concurrently with the four-day Vermont walking tours making it an ideal choice for couples, friends or family traveling together who have different interests. One or more people in the group may do the biking tour while others may select the walking tour. Both tour groups will stay in the same lodging and eat together. Some portions of the tour days overlap and both groups do the beautiful walk on the last day all together. Frequent Adventurers, GFA alumni, may deduct 5% from the tour price. Please contact us for youth and group rates. Custom dates and duration are available for groups of six or more.

Be The First To Know About New Tours

Be the first to get latest updates and information about new tours straight to your email inbox.