VT Shorts & Sweet Tour

3 Day Adventure




  • Street Biking
  • Wellness


  • Intermediate
  • Expert









  • 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 one of the oldest cheese-making operations in the US
  • Brewery visit
  • 2 knowledgeable guides
  • Van support
  • 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
  • Dedicated service throughout your worry-free tour

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

Lodging Options

Standard Room at Various Hotels and Inns

Max Occupancy: 2 Guests

Private 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.


Meals Included
Private Rooms



Meet 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

Departure Instructions

Meet at the inn in Woodstock at 1:30 pm on day one (address above). The trip is completed at approximately 12:00 pm on day three at the same place.

Booking Information

7 days prior to the adventure


Full payment is due at time of booking.


A booking may be cancelled within 30 days of the reservation with no penalty. See more details below.
A change to a different tour in the same calendar year will be allowed up to 60 days before the original tour departure date if space permits. There is no charge for this. Changes within 60 days of the original tour departure date are subject to cancellation fees as outlined below. Changes/transfers do not apply to custom tours.
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.)
If a tour is postponed by GFA due to COVID-19, all payments made will be applied as a credit for travel by 12/31/23 less any applicable third-party fees and a $150 per person administrative fee.


Travel and medical insurance are not included in this package. We strongly recommend that you purchase insurance to cover personal injury, cancellation, or interruption for your experience. You will need to separately purchase any trip interruption insurance through an outside provider. This must be done shortly after making your reservation (some require insurance to be purchased within 15-20 days of initial trip deposit).
We also recommend that you carry insurance to cover the risk of injury while you are at your destination. If you are injured, you will be charged the ambulance expenses associated with your evacuation as well as any expenses related to your medical care. Medical and evacuation insurance will help to cover these costs.

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