Woodstock VT Bike Tour
per person
Beguiling Woodstock, VT & Beyond Bike Tour
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!
Fall Photography
Some departures have an added perk. An expert photographer, whose widely published photos have been featured on the covers of Yankee Magazine and Vermont Life, will be available for portions of the tours. He will provide techniques and suggestions for creatively capturing the light and the tapestries of Vermont’s magnificent landscapes while bathed in radiant fall color. In the evening, he will offer helpful tips for improving your photos whether using a professional camera or simply your cell phone. He’ll share insights and secrets about how the experts create their remarkable compositions – along with sharing some of his own stunning photos!
Note: This biking 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 prefer the walking. All tour guests will stay in the same lodging and eat together. Some portions of the tour days will overlap as well.
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
Tour Reviews & Testimonials
“Our Vermont trip was better than we could have expected. It was the perfect way to celebrate our birthdays! We loved the routes and the timing of the fall color was perfect. The meals were great and we especially loved the farm dinner and the afternoon brew at Long Trail. The inn was the perfect place to stay and to relax. It was great to learn more about the area from people that know and understand the local culture, environment and history – we appreciated that Great Freedom Adventures is a locally (New England) based company. The guides were knowledgeable, supportive and fun. We loved having great information provided along the way about what we were seeing. We felt free to ride at our own pace but had support when we needed it. The snacks were awesome and we always felt well taken care of. We also enjoyed the final morning – with a pretty hike in the woods including a stunning view at the top – and the pie and cider at the end. Nice touch! It is evident how much care goes into planning the perfect experience. It was an amazing trip and we had a wonderful time!”
Lynn R.
“I wanted to reach out to tell you how much we enjoyed the trip. We have been on other commercial tours and your Vermont trip was one of the very best. Both guides were super-attentive, capable and good company as well. The routes were excellent. We have been telling our bike club buddies about Great Freedom and will go with you again.”
Anne H.
“Our Woodstock tour was so special to us! We thoroughly enjoyed the collegiate group and the great care given by our tour leaders and GFA staff. Kevin’s final night photo session was a highlight. We loved the well thought out route, the chance to be cycling leaf peepers, the flexibility to walk or ride, the perfect options for the wet day, the magnificent Woodstock Inn, the gourmet lunches, the perfect combination of 2 organised dinners and a free night and the company of such interesting people. I would recommend the tour to anyone.”
Dee & Stu O.
“What a great trip! We so appreciate your attention to detail and your gracious accommodation to everyone – and to our travel challenges. We really appreciate that you worked it out for us to ride on Wednesday afternoon when we got in late because of travel delays. We will definitely recommend Great Freedom Adventures! Thank you for a great vacation!”
Brent and Lori K.
“Our bike tour in Vermont was outstanding, beyond expectations. Our tour leaders were awesome. They thought of everything. WE HAD A BLAST!”
Michael B.
“We had a wonderful trip! The scenery on our bicycle rides was gorgeous!”
Dana F.
- DepartureWoodstock, Vermont
- Departure TimeEarly Afternoon
- Return TimeEarly Afternoon
- IncludeHiking TourBike Tour
- Not IncludedActive Vacation
From Our Gallery
Day 1
Meet 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.
Day 2
Bike 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.
Day 3
Pedal 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 46Day 4
After breakfast, take a 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. Please Contact Us for detailed itinerary and arrival and departure information.Our Gallery
Woodstock Inn & Resort, Woodstock, VT - 3 Nights (Oct 11 departure)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. 
Blue Horse Inn, Woodstock, VT - 3 Nights (Oct 8 departure) Built in 1831, the riverfront Blue Horse Inn is a handsome Greek Revival mansion that contains large, luxurious, and beautifully appointed rooms. Elegant, yet relaxing common spaces provide the perfect opportunity for chatting by the fire, enjoying a glass of wine or curled up with a book. Sensational breakfasts are taken in the dining room or on the covered porch overlooking the pool, gardens, Ottaquechee River and Middle Covered Bridge. The inn is in the heart of Woodstock Village, walking distance to shops, galleries, restaurants and theater. Inn amenities include a heated outdoor pool, a library and a fire pit.
2021 Dates
October 8-11 | October 11-14
2021 Prices
$2,195, per person, based on double occupancy. Single Supplement: $750
Trip Length
4 days, 3 nights
Start/Finish
Woodstock, VT
Daily Mileage
21-37 with longer options if desired
Cycling Level
Moderate. Moderate-Challenging with longer distance options.
Terrain
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. Fall Photography: Some departures have an added perk. An expert photographer, whose widely published photos have been featured on the covers of Yankee Magazine and Vermont Life, will be available for portions of the tours. He will provide techniques and suggestions for creatively capturing the light and the tapestries of Vermont’s magnificent landscapes while bathed in radiant fall color. In the evening, he will offer helpful tips for improving your photos whether using a professional camera or simply your cell phone. He'll share insights and secrets about how the experts create their remarkable compositions - along with sharing some of his own stunning photos! 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 for meals and side excursions
- Featherweight, high visibility, reflective vest
- Waterbottle
- Dedicated service throughout your worry-free tour
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.
Please Contact Us for detailed itinerary and arrival and departure information.
