Presented by The Vermont Challenge LLC


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Our Roads Are Calling
We are excited to announce our all-new plan for the 2022 edition of the Vermont Challenge with two new, intimate tours.
The Shires: August 19-21
Northeast Kingdom, Averill Lake: September 10-12 (separate registration)

The Shires

The Shires tour is located in the southwest corner and in the Green Mountains of Vermont and is similar to our traditional Vermont Challenge. This tour will take place over 3 days, but it's now a relaxed tour allowing riders to enjoy our corner of Vermont at a casual pace. The tour includes all lunches and dinners. Limited to 35 riders.

Profiles of the Tours

In the Reimagining of the Vermont Challenge, it was perhaps the word "challenge" where we decided to focus our attention. Rather than conveying the notion of competitive cycling with insurmountable climbs and no opportunity for considering the beautiful surroundings of Vermont, we decided to apply the brakes (no pun intended) and create a Tour that specifically meets the needs of those wishing to see and enjoy Vermont – all from the saddle of their bikes. A strong social element was important to add to the new, 2022 reimagined Tours and so emphasis on a much smaller, intimate group was decided upon.

Setting Expectations

Each days' rides will be led by seasoned ride leaders who will shepherd you through the hills and valleys of Vermont. These rides are planned to be casual scenic tours where the actual "challenge" will be determining which country store is the most quaint or which vista is the most beautiful. It's important to know that these two tours will be ridden at a much slower pace than in the past in order to accommodate our riders expecting a true biking tour.

The Shires Tour
3-day tour August 19-21 – $599
Includes all lunches and dinners
Excludes lodging*

3 consecutive days of riding
Limit total registrations to 35 riders
Route lengths/pace – two lengths to choose from: Mid 30's and mid 50's lengths daily, broken into two average paces
Each ride will receive a water bottle & a specialized exclusive gender specific tech top
We will offer all lunches and dinners (locations to be announced)
Tours offer support/refueling vehicle
Will provide a list of all services on all routes. These files should be uploaded to your phone
We'll stop at key locations like Country Stores etc.

Learn More
Please visit:

Online Registration Deadline: Saturday, Aug 6, 2022 at 5:00 PM ET

Total Event Registration Limit: 35

Select Your Category

Individual Entry
Category Start Time Field Limit Fee
Sold Out Shires Tour 8/18-21 $599 Aug 21
35 $599
  • Top rated 3-day tour of the Green Mountain state. The Shires
    4-day tour August 19-21 – $599
    Includes all lunches and dinners
    Excludes lodging*

Location & Contact

Location address:
340 Rec Park RD, Manchester, VT  05255
Event Phone Number:
(203) 668-0194
Event Website
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