Why Ride The Vermont Challenge?
The Vermont Challenge is the only bicycle Challenge that tours Southern and Central Vermont over 3 or 4 days and draws upon the creative energy of local businesses and people of Vermont, key ski resorts, restaurants and farms in each local community that we visit. We offer cyclists the chance to complete a century over one of Vermont's legendary "Gaps" across the spine of the Green Mountains with stunning vistas in each direction. The Vermont Challenge will become a major bicycling event in the United States and YOU can be part of this special event in its first year and be the proud owner of our commemorative first year jersey!
Day One: August 16th
Long Route - 52 miles
2,087 ft of climbing
Stratton Mountain Resort to Manchester
Short Route - 38 miles
1,801 ft of climbing
Stratton Mountain Resort to Manchester
Day Two: August 17th
Long Route - 64 miles
2,828 ft of climbing
Manchester to Okemo Mountain Resort
Short Route - 53 miles
2,156 ft of climbing
Manchester to Okemo Mountain Resort
Day Three: August 18th
The Gap Century for the 4-day & 3-day Tours
4,964 ft of climbing
Okemo Mountain Resort to The Town of Killington
Short Route - 48 miles
2,156 ft of climbing
Okemo Mountain Resort to The Town of Killington
One-Day Legendary Century - 100 Miles
5,089 ft of climbing
Okemo Mountain Resort to Okemo Mountain Resort
One-Day Half Century - 55 Miles
1,795 ft of climbing
Okemo Mountain Resort to Okemo Mountain Resort
Day Four: August 19th
Long Route - 60 miles
2,306 ft of climbing
The Town of Killington to Stratton Mountain Resort
Day Four: August 19th
Short Route - 46 miles
1,899 ft of climbing
The Town of Killington to Magic Mountain
Please note:
All climbing feet are approximate and based
on the capabilities of various mapping software.
Tour Arrivals
Grand Tour Arrival Day: Wednesday August 15th - Stratton Mountain Resort
Join us at the Kick-off Party at Stratton Mountain Resort after registering! The kick-off party is included for those who have signed up for the 4-day package! There will be a sponsor expo at the Stratton Base area, along with local bands playing and bike tune-ups. The dinner at Stratton Mountain Resort will be offered by the Farm to Table farming communities and local restaurants.

Weekend Tour Arrival Day: Thursday August 16th - Manchester
Those of you that plan to ride The Weekend Tour should plan to arrive Thursday afternoon to register and get situated at your hotel. There will be a sponsor expo at a central location in Manchester for you to enjoy.

One-Day Legendary "Gap" Century/Half-Century Arrival: Saturday August 18th - Okemo Mountain Resort, Jackson Gore
Those of you that plan to ride the one-day century/half-century should plan to arrive Saturday morning by 7am to register and prepare for your ride. There will be a sponsor expo at Jackson-Gore before and after the ride.
Meal Options
Rest Stops
Rest stops will be offering food and nourishment at roughly 20 - 25 mile intervals on all routes.

Lunch
Lunch is included daily in all packages at the following locations.
     Thursday August 16th: Manchester
     Friday August 17th: Okemo Mountain Resort
     Saturday August 18th: The Town of Killington
     Sunday August 19th: Stratton Mountain Resort
1-day Legendary Gap Century/Half-Century riders will have lunch at Okemo Mountain Resort

Dinner
The 4-day Grand Tour package includes a kick-off dinner at Stratton Mountain Resort on August 15th, and dinner at Okemo Mountain Resort on August 17th. Dinner is not included on August 16th or 17th in Manchester and The Town of Killington; riders are on their own to select from a variety of local restaurants! The 3-day Grand Weekend package includes dinner at Okemo Mountain Resort on August 17th.