Skip to Content
Vermont Challenge Logo
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 but here are our two Sponsor Hotels:

Vermont Challenge Sponsor Motels/Hotels:

Stratton Logo
Black Bear Lodge and other properties at Stratton Mountain
Black Bear Lodge offers reasonable rates and a full mountain experience with an active base village with shops and restaurants. You'll have to drive down to Manchester for 3 starts, but be right there for Saturday's start. Website: click here. Call 800-787-2886 for reservations and say you want the Vermont Challenge rates.

Taconic Logo
Taconic Hotel, Manchester
Website: click here. Guests may also call our central reservations line at 877-699-3331 and say they are with the Vermont Challenge Room Block or by giving this code: J52

Palmer House Logo
Palmer House Resort, Manchester
Centrally located within Manchester Center and a 5 minute walk into the bustling town with many restaurants and shops. Palmer House Resort offers indoor/outdoor pools, fitness center, tennis courts, 9-hole golf course, shuffleboard, and more! You'll be right there for our starts on Thursday, Friday and Sunday. Website: For reservations: 802-362-3600 and mention the Vermont Challenge, or click here to book online.


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

Copyright © 2020 The Vermont Challenge LLC. All rights reserved.