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The Vermont Challenge



August 16-19, 2012
The Vermont Challenge is a four, three, or one-day, non-competitive bike tour of Vermont!
Register now!

The Grand Challenge
The Grand Challenge begins at Stratton Mountain Resort on the evening of Wednesday, August 15th. The Grand Tour then continues to Manchester, Okemo Mountain Resort and The Town of Killington before returning to Stratton Mountain Resort on Sunday, August 19th. This route offers some of the best cycling roads you'll find in the U.S. In addition, you have the option of completing an amazing century on Saturday August 18th that crosses the Middlebury Gap, one of Vermont's six Legendary Gaps across the Green Mountains before finishing that day on the access road at The Town of Killington!

The Weekend Challenge
Short on time? Then choose the Weekend Challenge that begins Thursday evening, August 16th in Manchester and finishes back at Stratton Mountain Resort on Sunday, August 19th. This route, like the Grand Tour, provides you with the option of completing an amazing century that crosses the Middlebury Gap, one of Vermont's six Legendary Gaps across the Green Mountains. We offer bus transportation back to Manchester on Sunday since you started there, or you have the option to ride down the ridge for a fast downhill finish!

The One-Day Legendary Gap Century & Half Century
Can't take a day off from work, but want to really challenge yourself? Then come ride the one-day Legendary Gap Century/Half Century which begins and ends at Okemo Mountain Resort on Saturday August 18th and crosses the legendary Brandon Gap before returning to Okemo Mountain Resort's Jackson Gore lodge for lunch and a party. If you enjoy the Challenge of the Grand Fondo's or the Harpoon B2B you'll love the Gap Century Challenge! Or, ask about the half-century option.

Killington Lodging Partners:

All lodging partners will provide secure bike storage, a Sunday morning breakfast, and assistance with transportation throughout town.  Book at one of the partner properties below and your luggage will be delivered to the hotel before your arrival! 

Grey Bonnet Inn: Nestled on 25 wooded acres, the Grey Bonnet Inn awaits you with all the pleasures of a superb country inn.  Enjoy 41 charming rooms, common areas, pool, sauna, whirlpool and more, plus year round recreation.  Rates for Vermont Challenge participants start at just $88.92 per night with tax, and include a hot breakfast and secure bike storage in the lobby.

(802) 775-2573 or

Snowed Inn:  Rooms for Vermont Challenge Participants start at $89 per night, and include secure bike storage. Included in the price is an expanded continental breakfast - homebaked items, make your own Belgian waffle station with toppings, yogurt, granola, cereal, bagels, English muffins, and hardboiled eggs. 

(800) 311-5406 or

Or, book your lodging for all stops on the Challenge!

The Vermont Challenge has partnered with Resort Accommodations to offer services to plan your lodging for every night of the tour. Rather than booking town by town, Resort accomodations will create a package for you that includes your lodging - and that way, you can be sure your daily transition will go smoothly from one property to the next no matter which town you're in.

Resort Accommodations can book your lodging at one of more than ten properties in town, ranging from low-key and laid-back to upscale and personalized. Visit their website to learn more about booking your trip with Resort Accomodations - or keep it simple, and book with one of our preferred lodging partners above!