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The Vermont Challenge offers bicyclist's a truly unique ride experience 

The 2014 edition of the Vermont Challenge begins on 8/14, just one month from today at Stratton Mountain.  Join us for a challenging tour you won't soon forget!

The success of any ride begins with your energy and enthusiasm and the friendly-ness of our volunteers.  That combination is what makes the Vermont Challenge Vermont's premier bicycling tour!

Join us for the 3rd edition of the Vermont Challenge that offers great routes, amazing scenery, friendly volunteers, awesome lunches and dinners and a great Jersey that's included in your registration fee.  Register today and you're guaranteed a Jersey, while supplies last

3 different challenging tours so pick the one that fits your schedule, but we strongly urge you to consider riding all 4 days as that's our signature event at 275 miles or 220 miles in total.

  • Grand Tour - 220 or up to 275 miles
    • Complete 4-day tour $449 
    • Voted by last year's riders as the best experience and value
    • Includes one Day Gran Fondo Saturday
  • Weekend Tour -150 up to 225 miles
    • 3 day $339
    • Long weekend option
    • Includes one Day Gran Fondo Saturday
  • One Day Gran Fondo Challenge - 101, 73, 63, 23 miles
    • $189
    • Includes one Day Gran Fondo Saturday
    • Shorter route options of 63 and 73 miles
  • All registrations include 6% VT sales taxes
  • Excludes BikeReg registration fees
  • Lodging not included but reservations can be made at:

What's included in your registration fee:

  • Vermont Challenge Tech T-shirt
  • Vermont Challenge Jersey - one of the finest soft tech fabrics available
  • VTC Water Bottle
  • Fully stocked Goodie Bag: "The Vermont Challenge Goodie bag blows away all other rides I've ridden by far" - 2012 rider
  • All Meals associated with the tour you selected (Please see the About the Ride section for all meal details)
  • Fully-supported rest stops
  • Sag Support
  • Bike tech support each morning
  • Bus transportation with key venues
  • Nightly entertainment - great bands
  • Bus transportation back to Manchester for Weekend Tour riders
  • $25 of your registration fee is a tax-deductible contribution to the Stratton Foundation's Vermont Challenge Community fund that supports the towns we ride through. 

We listened to all your great suggestions and we've improved the Vermont Challenge 1-day ride and we'd love to have you join us again this year

 Improvements all included in your registration fee:

  1. Professionally timed Sprint & KOM segments on the long routes - medals awarded across 6 age categories by gender
  2. Pasta, chicken, salad, etc., dinner on Friday night at the Lookout Restaurant 
  3. Full finish lunch at Lookout
  4. Additional rest stop in Whiting, total of 4 fully supported rest stops every 25-30 miles
  5. More protein breakfasts at all participating hotels beginning at 6 am
  6. Larger arrows - 3 arrows before turns beginning 300 ft before turn on downhills and one confirming arrow
  7. Trailing sag support
  8. Jersey, Tech T-shirt, water bottle & matching socks included in your registration fee if you register before 8/1
  9. $25 of your registration fee goes to the Stratton Foundation in support of our 4 community groups that feed Vermonters in need

Please join us for 3rd edition of the Vermont Challenge.  If you have more time, then why not ride all 3 or 4 days?  It's a great experience and you'll meet other passionate riders just like you!


All volunteers receive a T-shirt and water bottle and participate in the group meals on the day they are working. If you volunteer for 2 days, you may choose to ride on the 3rd day at no expense. If you volunteer for 3 days you can ride 1 day at no expense and you'll also receive a jersey with our compliments.

 Please go to, to register as a volunteer.


Giving back to Vermont's Communities through the Stratton Foundation

$25 of your registration fee will be a donation to the Stratton Foundation to help support the communities we'll be riding through. This will be a tax deductible contribution. Last year we contributed $6,000 to four community groups that help feed those in need within the communities we ride through:


Black River Good Neighbors - serving families in Ludlow, Cavendish, Proctorsville, Plymouth, and Mountain Holly. 


Jamaica/Wardsboro Community Food Pantry serves families with young children, the elderly and those who by illness or circumstance find themselves in crisis.


BROC Community Action & Rutland Methodist Church 'Feed the Freezer' - providing nutritious homemade frozen casseroles and meals to low-income individuals & families throughout Rutland County. 


Meals on Wheels - Community meals serve approximately 200 individuals daily in the Bennington Senior Center and Manchester Town Hall. 

The Vermont Challenge offers bicyclist's a truly unique ride experience