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About the Challenge

The Vermont Challenge is comprised of four glorious days of riding with riders from across the U.S. and Canada. Come ride through the picturesque countryside, covered bridges, river valleys and historic villages of south and central Vermont. The Vermont Challenge is scheduled for August 16–19, 2018.

Challenge Options

We reconfigured the Vermont Challenge routes creating a 2-day "Valley" & 2-day "Mountain" Challenge. Two amazing experiences for you to choose from or challenge yourself and ride all 4-days for the best experience at a fraction of packaged tour prices. We also offer a 3-day package so you can ride from Thursday through Saturday or Friday to Sunday and create a combination of valley and mountain rides that fit your schedule.

Route Overview by Day

Valley Stages - Thompson Park Manchester:
Mountain Stages - Stratton Mountain Resort:

Pricing and What's Included


The Package

All riders receive the following for riding the tour.


The Pricing

We donate $30.00 of your registration fee to our Beneficiaries through the Stratton Foundation. You will receive a letter thanking you and acknowledging your contribution. You are most welcome to make an additional contribution.

The 4-day Grand Challenge – August 16-19


Voted by last year's riders as the best experience and value. Includes the one-day Gran Fondo on Saturday, August 19 and kick-off meet and greet dinner at the Manchester Country Club.


The 3-day Challenge – any 3-days from August 16-19 (can be non-consecutive)


Includes the one-day Gran Fondo Saturday, August 18.


The 2-day Challenge – any 2-days from August 16-19 Choose either 2 Valley or 2 Mountain stages


Vermont Challenge Fondo (Saturday, August 18: The Gran, Medio, Gran Piccolo or Piccolo) or choose another day of your choice to ride


Please note: Ride registration excludes 6% Vermont sales tax and Bike Reg service fees, which will be added to your total at time of check out.

Vermont Challenge Highlights and Family Activities

Daily highlights for Riders and their families:

Wednesday, August 15
  • Kick-off dinner for riders and their families ($25 for each family member) at the Taconic Hotel, a Kympton resort
Thursday, August 16
  • Farm to table lunch for riders and their families at Dana Thompson Park ($16 for each family member)
  • Manchester Farmer Market and Crafts, Manchester, VT
Friday, August 17
  • Farm to table lunch for riders and their families at Dana Thompson Park ($16 for each family member)
  • Group dinner at Stratton Mountain Resort ($25 for each family member)
Saturday, August 19
  • BBQ lunch for riders ($16 for each family member)
  • Bike Festival and music, featuring "Don't Leave"
  • Evening Concert "Pink Floyd music and laser light show" (Extra charge – tickets available on Stratton's web site)
Sunday, August 20
  • Finale Lunch at Stratton Mountain Resort ($25 for each family member)
Other family activities available in the area:
  • Canoeing and tubing down the Battenkill River
  • Hiking trails at Stratton, Hildene and the West river trail
  • Family adventure park at Bromley Mountain Resort
  • Community Pool for swimming at Dana Thompson Park
  • Vermont Country Store in Weston
  • Shopping at the outlets in Manchester, VT
  • Fly fishing along the banks of the Battenkill River
  • Golf courses at: Stratton, Equinox in Manchester and many more
  • Drive up Equinox Mountain at 4000 ft the highest point in the Taconic Range


An event of this size and scope is a success due to its volunteers. 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'll receive a 2018 VT Challenge jersey. If you volunteer for 3 days you can ride 1 day at no expense and you'll also receive a jersey with our compliments. If you are considering volunteering, please click on the button below and select a day or days you wish to volunteer and choose a spot.


The Vermont Challenge would not be possible without great partners. If you are considering becoming a sponsor, please go to the Sponsorships page.


The Vermont Challenge is pleased to announce that with the generous contributions made by those who participated in past Vermont Challenges, we've made equal donations to the following organizations:

We're donating part of your registration fee again this year!
We thank all those riders that made donations and collected funds from friends and family during past tours. This year we will once again be taking a portion of each rider's registration fee and donating putting it toward the Vermont Challenge Community fund, administered by the Stratton Foundation. Riders will be also be able to continue to make addition donations. All donations are 100% tax deductible as allowed by the IRS. As the Vermont Challenge grows in stature we'll continue to increase the amount funds donated to support the communities that host our ride

Donating & Fundraising

The Vermont Challenge takes a portion of your registration fee and donates those funds to the community groups listed above through the Stratton Foundation. Fundraising or donating is not required, but we ask you to consider being generous in making a donation to give back to the great people of Vermont that could really use our help.

To help you make this easy for you, we've teamed up with My Charity of Choice. My Charity of Choice is an innovative social fundraising site that provides a crowd funding engine that allows you to raise money for the Stratton Foundation which is our charity or a charity of your choice. We hope you'll choose to support our groups, but you can chose to support those that are important to you.

To donate to the Stratton Foundation to support the Vermont Challenge community groups, just click on the button here.


To create your own campaign donating through the Vermont Challenge to a charity of your choice, just click on the button here.