Presented by The Vermont Challenge LLC.


Online Registration is closed

Registration is open for the 9th annual Vermont Challenge, New England's premier multi-day tour

The Tours of the Vermont Challenge are experienced leader lead scenic rides at a fraction of package tours. Our 2020 tour is limited to 100 riders, so our spots fill up fast. You'll experience four glorious days of riding through some of the most picturesque countryside, covered bridges, river valleys and historic villages in the world.

What makes the Vermont Challenge so special?

It's first and foremost Vermont itself

Everything from our scenic roads to our friendly people. Our rolling hills, dairy farms and quiet country roads are calling you to join us. Our philosophy has always been to focus on scenic Vermont and its local flavor.

Then it's our format

We limit the field, so you get to know your fellow riders who come from all over the U.S. and Canada. We then add talented ride leaders to help guide you each day. We limit groups to roughly 15 riders per leader. This gives us a better opportunity to concentrate our efforts on the riders touring experience.

Changes to our format from last year

Last year was our first under the new format, so we're making changes to improve on last year's tour: More stationary rest stops and more support vehicles on each of the daily routes. Each ride leader will focus on YOU and ensure you have the best possible experience riding with us!

Routes Revisited

As we have over the last 8 years, we'll again tinker with our routes to add a twist for all of you who have joined us before.

Destination Points

We are selecting special local businesses where we stop and sample food or tour a location. This is the advantage of taking riders out in groups. Cyclists can meet and ride with the same people and get to know one another through riding, eating and touring.


We'll be once again offering four sumptuous farm-to-table lunches at the end of each day's tour. We will also be offering a kick-off dinner on Wednesday evening after check-in, as well as on Friday. On Thursday and Saturday you are free to explore the area for dining venues.

Learn More
Please visit:

Online Registration Deadline: Thursday, Aug 13, 2020 at 5:00 PM ET

Select Your Category

Individual Entry
Category Field Limit Fee
closed 4-day Grand Tour 8/15-18 $549 $549
  • Top rated 4-day tour of the Green Mountain state. The Vermont Challenge is limited to 100 riders

Location & Contact

Location address:
Village Lodge Road, Stratton Mountain, VT  05340
Event Phone Number:
(203) 668-0194
Event Website
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