Best of Vermont Bike Tour | Great Freedom Adventures
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Best of Vermont Bike Tour

Best of Vermont Bike Tour

per person

Best of Vermont Bike Tour


The Essence of Yankee Life and Land
We’ve been biking all over Vermont for 35 years but we keep coming back to central Vermont. The scenery is varied and spectacular and the towns around which the tour is based are among the loveliest in all of Vermont.  The best of central Vermont has been distilled into one fabulous trip – the best biking routes, restaurants with the best chefs, lovely inns, a hike with unsurpassed views, and visits to the most interesting sights. Give us six days and we’ll give you the best of central Vermont and a bit of New Hampshire too. Come experience a New England bike trip that captures the essence of Yankee life and land.

Vermont Bicycling

Idyllic Vermont Bicycling
Great Freedom Adventures’ six-day Vermont bike tour meanders alongside idyllic dairy farms, past classic red barns on quiet country roads. Bike past sparkling lakes and rivers with plunging waterfalls. Feel like a kid again by jumping into a crystal clear swimming hole.  Cross historic covered bridges and discover a dramatic 163’ gorge.

bethonbikeresizedFascinating Vermont Sites
On this New England bike trip, wind through picturesque Vermont towns where white steepled churches surround the town green. And, explore a bit of New Hampshire along the way. Hanover, home of Dartmouth College, is bustling with youthful energy and blessed with New England charm. The many fine shops and cafes wait to tempt you. See master artisans at work at the renowned Simon Pearce glassblowing shop and sample the artisanal cheese at the Plymouth Cheese Factory, founded by President Calvin Coolidge’s father.  Tour the Calvin Coolidge State Historic Site, where Coolidge was sworn in as President by his father in 1923.  The homestead is exactly as it was on the night he was sworn in and in fact, the entire village of Plymouth Notch is largely unchanged since the early 20th century.

Vermont’s Only National Park
Visit Vermont’s Marsh-Billings-Rockefeller National Historic Park and tour the farm and mansion grounds. The farm is the boyhood home of George Perkins Marsh one of America’s first environmentalists.

20-foot-hole-resizedWoodstock – “The Prettiest Small Town in America”
Woodstock is bound to be a highlight on this Vermont bike tour.  Because there is so much to experience in this very special place, the trip has been designed to afford opportunities to become immersed in Woodstock’s many charms.  Explore the unique shops and exquisite galleries lining the flower-filled streets. View historic homes, and hike peaceful trails leading to stunning views.  Take a nighttime stroll along lantern-lined streets to one of the lovely bridges.  Listen to the water gurgle underneath while overhead the sky sparkles with more stars than you may ever have seen before.

Daily Exercise – Nightly Rewards
Bike carefully crafted routes that showcase the best of Vermont’s gorgeous countryside and experience this beauty with all five senses. Reward each day’s efforts by relaxing at the pool, sipping a drink on the veranda and dining on exceptional meals fresh from Vermont farms. Come experience the Best of Vermont Bike Tour for an unforgettable Vermont vacation!

Tour Highlights:

  • Stay in beautiful inns offering fine amenities
  • Dine on meals prepared by some of the region’s best chefs
  • Bicycle the most beautiful roads in central Vermont
  • View dramatic Quechee Gorge
  • Visit a working 1,000 acre hilltop farm and dine at the stunning post and beam restaurant on gourmet food fresh from the farm
  • Visit Billings Farm and Museum
  • Explore the Marsh –Billings-Rockefeller National Historic Park
  • Enjoy a private beer tasting of some of Vermont’s best craft beers
  • Hike to panoramic hilltop views
  • View cheesemaking at the oldest cheese factory in the US
  • Visit Calvin Coolidge State Historic Site
  • Watch master glassblowing artisans at work at renowned Simon Pearce
  • Visit a brewery and sample the brews
  • Bike over covered bridges, past idyllic farms and cascading waterfalls
  • Stroll through lush gardens designed by renowned landscape architects
  • Sample the treats at charming country stores
  • Shop in fine stores, galleries and antique shops

    Day 1

    vermont-bike-trip_000Meet in Woodstock at the 506 On the River Inn for a welcome lunch and bike fitting. Bike north on pastoral roads to an idyllic place set amidst horse farms and surrounded by the Green Mountains. The picture perfect Three Stallion Inn and Resort epitomizes gracious Vermont country living. In season, take a dip in the pool or hike some of the many lovely trails. Later, sip a drink on the veranda overlooking the golf course and watch the sun set behind the mountains. Enjoy a locally-sourced, farm-to-table dinner prepared by highly respected chefs. Biking Mileage: 16

    Day 2

    vermont-bike-trips-2Today, pedal along the crest of ridgelines with Green Mountain vistas, discover sleepy New England hamlets, view productive dairy farms and see a floating bridge. Swim in the lake if you like, then continue cycling through this enchanting Vermont landscape.  Back at the inn, swim, walk the trails, or simply relax. Before dinner, enjoy a private beer tasting of some of Vermont's best craft beers. Biking Mileage: 32, 41 or 46

    Day 3

    vermont-tourThe sensory indulgence continues today with breathtaking long-range views and classic covered bridges, the smell of freshly cut hay or newly fallen leaves and the feel of the wind while coasting downhill.  Enjoy lunch at an old country store which doubles as the town’s news center. Arrive in Woodstock and if you wish, take some time to explore this lovely town. Relax at the luxurious 506 On the River Inn overlooking the Ottaquechee River.  Take a dip in the indoor pool, have a drink in the bistro or curl up with a book in the library or in one of many other inviting and beautifully decorated spaces. Dinner is on your own and your guides will be happy to recommend options. Biking Mileage: 36 or 54

    Day 4

    vermont-bike-trips-8Bike the loveliest roads in the hills and valleys around Woodstock. Pedal to the natural wonder of Quechee Gorge and look down to the Ottaquechee River 165' below as it flows through the narrow gorge. Visit Simon Pearce glassblowing workshop and store to watch master artisans create fine glassware sold in shops around the world. Riders choosing the long option will continue into Hanover, NH, a handsome town filled with upscale shops, excellent cafes and Dartmouth College students. For a sweet treat, head back to VT to the King Arthur Flour School and Store, an award-winning artisan bakery. Follow the river back to Woodstock, passing three covered bridges along the way. Enjoy dinner at a top Woodstock restaurant. Biking Mileage: 39 or 57

    Day 5

    vermont-bike-trip-2Pedal an area of manicured horse farms and handsome brick mansions. Travel through moose and beaver habitat, passing tranquil bogs, shaded streams and trout filled lakes. Visit the Calvin Coolidge State Park and Coolidge Homestead, a place largely unchanged from Coolidge's boyhood days.  Tour the homestead and the village of Plymouth Notch, listed on the National Register of Historic Places. Sample the artisan cheese at the Plymouth Cheese Factory, one of the country's oldest cheesemaking operations. Then, head down the road to wash down the cheese at the Long Trail Brewery. Dinner on the last night provides a unique experience. Visit a 1,000-acre working hilltop farm and dine in the post and beam restaurant offering long-range views of the valley below. The expert chef uses fresh, organic foods raised or grown right there on the farm. Bon Appetite! Biking Mileage: 34 or 42

    Day 6

    vermontbiketour4cyclistsAfter breakfast, visit the Billings Farm and Marsh-Billings-Rockefeller National Historic Park and mansion. Hike carriage roads and scenic trails to a hilltop with panoramic views of Woodstock, the meandering Ottaquechee River and a patchwork of green or golden fields. The beauty will surely take your breath away. Walk down, through the covered bridge, and back to town to complete a remarkable six day journey discovering some of the very best that Vermont has to offer.     Please Contact Us for detailed itinerary and arrival and departure information.


    506-on-the-river-inn506 On the River Inn, Woodstock, VT - 3 NightsThis fine new inn, recommended by Conde Nast Traveler as “the place to visit” in 2015, is set on the banks of the Ottaquechee River with balconied rooms overlooking the water. Inn amenities include a bistro, restaurant, country kitchen, library, game room, gift shop, and an indoor pool with sauna.
    woodstock-inn-2Woodstock Inn & Resort: 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 Dates

    Coming soon

    2018 Prices

    Coming soon

    Trip Length

    6 days, 5 nights


    Woodstock, VT

    Cycling Level

    Moderate (Moderate to Challenging with longer mileage options)

    Daily Mileage

    26-42 (Longer options: 26-55)


    Some short and long hills every day along with flat stretches. Occasional sections of dirt road.

    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. What's Included:
    • 6 days of bicycling and hiking
    • Free bicycle and helmet rental
    • 5 nights lodging
    • 5 breakfasts
    • 4 dinners
    • 1 lunch
    • Admission to
      • Billings Farm and Museum
      • Marsh-Billings-Rockefeller National Historic Site
      • Calvin Coolidge State Park and Coolidge Homestead
    • Brewery visit
    • Cheese factory visit
    • Wine cocktail Woodstock nights
    • Working farm visits
    • 2 dedicated guides
    • Van support
    • Luggage transport
    • Daily maps and cue sheets
    • Daily snacks and cold drinks
    • Tax and gratuities for meals and side excursions
    • Featherweight, high visibility, reflective mesh vest
    • Waterbottle
    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.

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