Vermont Bike Tours

Experience the Best Cycling in the Country on Our Vermont Bike Tours

Great Freedom Adventures is proud to offer unique Vermont bike tours with flexible schedules. Absorb spectacular mountain vistas in any season and discover hidden treasures like local swimming holes and secluded fields of wildflowers. Guests experience pastoral farmland with classic red barns, covered bridges, bustling towns, sleepy hamlets, panoramic mountain vistas, trickling streams, thundering waterfalls, maple sugar shacks, and much more. Wildlife abounds throughout, and guests may see moose, fox, deer, turkeys, and even eagles. In the fall, the radiant multi-colored fall canopies are awe-inspiring, while the thick greenery provides much needed shade and respite from the heat in the summer months.

  • 3 Day Adventure
  • May 5th – 7th – $1,695 (SOLD OUT)
  • June 4th – 6th – $1,695 (SOLD OUT)
  • July 21th – 23th – $1,695 (SOLD OUT)
  • August 18th – 20th – $1,695 (SOLD OUT)
  • October 2nd – 4th – $1,795 (SOLD OUT)
  • October 27th – 29th – $1,795 (SOLD OUT)
A group posing in front of lake during Vermont bike tours

Unforgettable memories guaranteed on our Vermont bike tours

Great Freedom Adventures has been running tours throughout New England and Vermont for several years. Our Vermont bike tours are unique due to our flexibility with our schedule. We like to call these tours ‘short and sweet’ – 3 day tours that explore all of the highlights of Vermont on bike. This tour still includes the best to offer on a bike tour – excellent lodging, unique cuisine, and scenic cycling. Our guides work hard to make sure your trip is seamless and memorable in the Green Mountain state. As our tours tend to fill, you’ll have the opportunity to meet travelers from all over the country, forming strong bonds and memories that last. A Vermont bike tour should be high on your list. Feel free to speak with one of our travel consultants to learn more about the tour, as well as other tours we offer. We look forward to speaking with you.


  • Fine accommodations in beautiful Woodstock, VT
  • Bicycle and helmet rental
  • 2 breakfasts
  • Admission to the Calvin Coolidge Homestead and Historic Site
  • Visit one of the oldest cheese-making operations in the US
  • Brewery visit
  • 2 knowledgeable guides
  • Van support
  • Daily maps and cue sheets
  • 2 dinners
  • 1 lunch
  • 2 breakfasts
  • Daily snacks and cold drinks
  • Tax and gratuities for meals and side excursions
  • Featherweight, high-visibility, reflective mesh vest
  • Waterbottle
  • Dedicated service throughout your worry-free tour


Inclusions and Amenities

All Inclusions and amenities are subject to change, should we change our stay or dinner options, comparable options will be provided. 

Packing List

  • 2 pairs of bike shorts so you can alternate every day
  • 1 pair of quick dry pants for cycling
  • 2-3 pairs of biking socks + 1 pair of waterproof socks
  • Bike shoes
  • 2 quick dry cycling jerseys + one long-sleeved jersey if the weather is colder
  • Arm warmers, leg warmers
  • Rain gear, including a helmet cover, shoe covers, pants, and jacket
  • Cycling gloves
  • Sunglasses
  • Bandana

Rider Level



Meals Included
Private Rooms

Lodging Options

Standard Room at Various Hotels and Inns

Max Occupancy: 2 Guests

Single supliment available

Throughout the tour, guests will stay in a selection of upscale Inns and Hotels along the way. As many are Historic Inns, rooms may vary in design, aesthetics, and layout. We’ve provided some sample images to give you a sense of what your accommodations may look like. Please note in the room selection process; we ask that you choose between a shared or double occupancy room and a private room for individual guests.



Meet in Woodstock. 


The trip is completed approximately 12:00 pm on day three in Woodstock.


Day 1:

In the early afternoon, meet in Woodstock and enjoy lunch while your guides fit your bike. Start your Vermont adventure pedaling to a picturesque hamlet with a quintessential country store, passing one of America’s oldest ski resorts. 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 coasting downhill for miles on the way back to Woodstock. Spend the afternoon relaxing in the pool at the inn. After, savor a delicious dinner of seasonal, local foods.

Biking Mileage: 22

Day 2:

After breakfast, embark on a ride through the countryside, passing equestrian estates and sleepy hamlets. Watch for mink, otter, beaver lodges, and moose habitats while pedaling through a 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. Sample the artisan cheese at the Plymouth Cheese Factory, started by Coolidge’s father. Down the road, we’ll stop at a microbrewery to sample some award-winning craft beer. For dinner, we will dine on expertly prepared and beautifully presented dishes.

Biking Mileage: 36 or  44


Day 3:

Today, the diverse beauty of Vermont continues to unfold. Bicycle along country roads with green or multi-colored leaves arching overhead; pedal through covered bridges and stop at classic country stores. Watch for roadside maple stands or “sugarbushes” with strung sap lines awaiting sugaring season. Trek to charming Quechee with its covered bridge, polo fields, powerful waterfall, and the renowned Simon Pearce Glassworks. Return to the inn to say goodbye to one another and the captivating sights, scents, and tastes of this charming part of Vermont.

Biking Mileage: 24

Booking Information


7 days prior to the adventure departure.


A deposit is due upon booking – $750 per person for five to eight day tours and $500 per person for three to four day tours. Payments may be made by check or credit card. Our receipt of the deposit, registration form, and signed Release form will secure your reservation.

An invoice for the balance will be emailed and final payment is due no later than 30 days (exceptions made for last minute booking) before the tour departure date. Payment may be made by check or online with a credit card. If final payment is not received by the due date, Great Freedom Adventures reserves the right to cancel the reservation.


All cancellations must be submitted in writing; refunds will be based on the day we receive written notice. Please purchase trip cancellation/travel insurance because exceptions to our cancellation policy cannot be made for any reason, including personal emergencies, illness or injury, canceled or delayed flights or ground travel to the tour departure point, or weather. Refunds will not be made for a participant arriving late or departing early from a tour, or for a participant not using accommodations, meals, or other services offered as part of a tour.

Cancellation Fees Are as Follows (Per Person):

Cancel 30 days or less from booking date – No charge (Does not apply to custom or private tours or to US tours booked within 60 days of departure or overseas tours booked within 90 days of departure.)
91 or more days before trip – $150
61-90 days before trip – $750 or $500 (loss of deposit)
31-60 days before trip – 50% of trip price
30 or less days before trip – 100% of trip price (20% of your payment may be applied to another of our tours departing within one year of original tour start date.)


Travel insurance is available from a number of insurers or their representatives, such as CSA Travel Protection or Travel Guard. You may compare prices and policies at Insure My Trip. We do not sell insurance or recommend any particular insurer or policy, but we highly recommend that you obtain travel insurance.