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Vermont Challenge:

Our roads are calling.

Learn More About the New Vermont Challenge

Our all new ride-led tour format offers consistent rollout times of 8:30 with two ride leaders for each of 3 routes. Each leader is well versed in route details for snack/drink stops, places of interest and picture taking. You will not only enjoy your tours, you'll also receive many special perks like two vouchers for dinners at three pre-determined restaurants, jersey, tee shirt, water bottle, a goodie bag, shopping and dining discounts and much more – all compliments of the Vermont Challenge.

Tour Info

What’s Included For 2020

Vermont Challenge Cycling Kit
All riders will receive a
2020 jersey. Register before 6/15.

Vermont Challenge T-shirt
Not the typical cotton T-tech. Moisture
wicking fabric.

Vermont Challenge Water Bottle
performance bottle.

Vermont Challenge Lunch
Farm to Table lunches each day after the ride.

Vermont Challenge Dinner
Vouchers for 2 dinners at 3 pre-determined restaurants.

Vermont Challenge Goodie Bag
The best fully stocked draw string goodie bag.

Vermont Challenge Shopping
Dining and shopping discounts in Manchester
and Stratton.

Vermont Challenge Tech Support
Tech support
at each start.


As part of the planning of the Tours of the Vermont Challenge, budget concerns were factor into our new format for pricing. Unlike other tour packages, where participants lodge together, The Vermont Challenge lets its rider choose for themselves where they wish to lodge so they can control their own budgets. So there are no lodging fees added into our tour package price. Manchester and Stratton offer numerous lodging choices depending on your needs and desires.

Exclusive Vermont Challenge Lodging Partners

Palmer House Logo
Manchester: Palmer House
5383 Main St, Manchester Center, VT 05255   802-362-3600
Our exclusive Lodging partner in Manchester is the Palmer House. Palmer House is centrally located with access to all Vermont Challenge starting points via bike or a short car ride. To make reservations: click here.

Stratton Logo
Stratton Mountain Resort: Black Bear Lodge
Black Bear Lodge offers reasonable rates and allows riders to walk to our start on Saturday. You'll need a car to access Thursday, Friday and Sunday's rides down valley. Reservation link will be up shortly.


Day 1 of the Vermont Challenge.


The Vermont Challenge mission is to provide the ultimate riding experience while striking a balance between the touring rider and the more serious cyclist. Offering a variety of scenic destinations that provide an authentic Vermont experience is our number one goal.

460 Stratton Gate Rd
PO Box 203, Jamaica VT 05343

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