3 Day Vermont Bike Trips | Biking & Walking Tours | Great Freedom Adventures
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Short & Very Sweet VT Bike Trip

Short & Very Sweet VT Bike Trip

per person


3 Day Vermont Bike Trips

Maple Sugar, Artisan Cheese and Vermont Beer
Spend three sweet days discovering maple sugar shacks and savor maple candies in country stores, artisan cheese, freshly pressed cider, locally brewed beer and delectable meals in top-notch restaurants. Burn off those calories and more while biking past red barns on classic dairy farms, dramatic gorges, sparkling rivers and pristine lakes.

Short and Very Sweet Vermont Bike Trips

Covered Bridges, Country Stores and Wildlife
Bicycle through covered bridges, along pastoral back roads to stunning Green Mountain views. Listen for the distinctive thrash of foraging moose or the cry of a soaring eagle while pedaling past bogs and wildflower-filled meadows. Meet friendly Vermonters and encounter that indomitable Yankee spirit while witnessing the most beautiful landscapes and intriguing sights in central Vermont. This carefully crafted, guided and supported bike tour draws from 34 years of Vermont bike touring experience to treat you to the sweetest morsels in a few short days for a captivating slice of New England heaven.

Tour Highlights:

  • Stay at a fine Woodstock inn offering upscale amenities and a quintessential Vermont experience
  • Savor foods fresh from the farm and prepared by talented chefs
  • Explore Woodstock, one of the “prettiest small towns in America”
  • Bike quiet roads through a pastoral landscape of dairy farms, wildlife areas, sugarbushes, country stores, river valleys, covered bridges and classic New England towns
  • View dramatic Quechee Gorge and cascading waterfalls
  • Visit Calvin Coolidge State Historic Site
  • Taste a variety of cheeses at the oldest working cheese factory in the US and discover how cheese was made then and now
  • Visit a brewery and sample the brews
  • Watch master glassblowers create exquisite glassware at renowned Simon Pearce
  • Shop in unique stores, local artist’s galleries and antique shops

Day 1

3-day-vt-bike-toursMeet in Woodstock in the early afternoon and enjoy lunch while your guides fit your bike. Embark on your Vermont adventure, pedaling to a picturesque hamlet with its country store, passing one of the oldest ski areas in the country. Relax on the shores of a sparkling lake, not far from where Sinclair Lewis once wrote and vacationed. A gradual climb out of town is rewarded by miles of easy downhill on the return to Woodstock. Relax at the inn, then stroll through the beguiling town to the restaurant and enjoy a fine dinner together. Biking Mileage: 21

Day 2

3-day-vt-bike-tripsAfter breakfast, bicycle through countryside of handsome equestrian estates, past one of the oldest horse associations in the country. Continue through sleepy hamlets and a wildlife management area of beaver lodges and moose habitat. Watch for mink and otter too while pedaling through this unique ecosystem of bogs, seeps, vernal pools and ponds. Climb to a ridgeline with sweeping views then coast downhill past crystal clear lakes and streams en route to the Calvin Coolidge Homestead. Walk in the footsteps of this former president then sample the artisan cheese at the Plymouth Cheese Factory, started by Coolidge's father. Coast down the road to a microbrewery to sample some of the award-winning craft beer. Enjoy dinner at a top-notch restaurant with expertly prepared and beautifully presented dishes. Biking Mileage: 36 or 44

Day 3

fall-foliage-bike-tours-gfa-12Today, the diverse beauty of Vermont continues to unfold. Pedal through covered bridges and stop at classic country stores. Bicycle along country roads with green or multi-colored leaves arching overhead that make you feel like you are biking through a postcard. Watch for roadside maple stands or “sugarbushes” with strung sap lines awaiting sugaring season. Pedal to charming Quechee with its covered bridge, polo fields, powerful waterfall and the renowned Simon Pearce Glassworks. Watch master glassblowers create masterpieces, then head to the Quechee Gorge to view one of Mother Nature’s masterpieces. Spin along the river passing horse farms and gracious country estates. Return to the inn to say goodbye to one another and to the captivating sights, scents and tastes of this very sweet part of Vermont. Biking Mileage: 20

506-on-the-river-inn506 On the River Inn, Woodstock, VT - 2 NightsThis 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.

Three Day Guided Bike Tour

2017 Dates

May 26-28 | July 23-25 | July 28-30 | August 4-6 | September 29-October 1 | October 6-8

2017 Prices

May - August: $995, September - October: $1,195, Per person, based on double occupancy. Single Supplement: $495

Special Charity Tour

July 28-30 is a special charity tour open to all. Raise money and take an awesome tour too!

Trip Length

3 days, 2 nights


Woodstock, Vermont

Cycling level

Moderate. Moderate-Challenging with long option.

Daily mileage

20-36 (44 with long option)


Flat along the rivers with hills outside the river valleys. 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:
  • Fine accommodations in beautiful Woodstock, VT
  • Bicycle and helmet rental
  • 2 breakfasts
  • 2 dinners
  • 2 lunches
  • Admission to the Calvin Coolidge Homestead and Historic Site
  • Visit to one of the oldest cheesemaking operations in the US
  • Brewery visit
  • 2 knowledgeable guides
  • Van support
  • Daily maps and cue sheets
  • Daily snacks and cold drinks
  • Gratuities at inn and restaurants
  • Featherweight, high-visibility, reflective mesh 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.

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