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  • Saint-Hermenegilde, Quebec
  • Vermont Farm
  • Saint-Hermenegilde, Quebec
  • Vermont Farm

Our Roads Are Calling

We are in the process of planning for 2024 season, which will includes two very different, small group tours.

Manchester, VT Manchester, VT

The Shires

The Shires tour takes place in the southwest corner of Vermont in the Green Mountains and is like our traditional Vermont Challenges done in the past. This Shires tour will take place over 3 days led by experienced ride leaders allowing riders to enjoy our corner of Vermont. The tour includes all lunches and dinners. Limited to a TBA amount of riders.
Averill Lake Averill Lake

Northeast Kingdom

Introduced in 2022, this new tour is in northeastern Vermont, which sits on the Canadian border and just west of the New Hampshire state line. The lodging (shared rooms and bath) for this tour is a large home right on Averill Lake in the most beautiful part of rural Vermont. You'll enjoy an all-inclusive 3 days of relaxed touring, which includes all meals. Enjoy afternoons right on the lake for swimming, kayaking, exploring or simply kicking back with a good book. Rides will take us in and out of Canada, so a Passport (passeports requis) is a MUST. Limited to 20 riders.
Vermont Valley View

Profiles of the Tours

Vermont License Plate
The Tours of the Vermont Challenge in 2024 offer ride leader lead routes unlike the one's on our route-arrowed, leaderless tours. These tours are designed to specifically meets the needs of those wishing to see and enjoy Vermont – all from the saddle of their bikes.

Setting Expectations

Quebec License Plate
Each days' rides will be led by seasoned ride leaders who will lead you through the hills and valleys of Vermont on the Shires Tour and Vermont, New Hampshire and Québec for the Northeast Kingdom Tour. These routes are designed for riders who ride a fairly regular basis and have ridden 30 or more miles on multiple days.
Vermont Farm
The Shires Tour
Tour details to be announced

Shires Tour Pricing
Tour pricing to be announced

The Past Tour Jersey
2023 Vermont Challenge Jersey
The jersey for 2023 was an all new design that features elements of both The Shires and the Northeast Kingdom Tours.
The front side design elements, with it's pine trees, rolling hills and valleys, and covered bridge, all represents the Shires Tour held in July and where all rides are ridden in the Green Mountains Region of Vermont.
The back side features evergreens, moose and rolling hills that are typical elements associated with the Northeast Kingdom of Vermont and the Great North Woods of New Hampshire. More specifically it includes the motto Je me souviens (I remember) and a fleur-de-lis pattern to represent Québec, Canada where a number of our rides are ridden.
To see a large image of the jersey, click here or on the image itself.
Note: This jersey is no longer available for purchase.
Lake Averill
The Northeast Kingdom Tour
Tour details to be announced

Je me souviens - I remember

Northeast Kingdom Cyclists Northeast Kingdom Cyclists
Je me souviens is the motto of Québec Province. There are days where we will be riding in and out of Québec or starting and finishing our rides in Québec. Although Canada, in some places is only mere meters/feet from the Vermont border, where neighbors actually live in another country, just remember you will actually be in another country so make sure your passport is up-to-date.

Northeast Kingdom Tour Pricing
Tour pricing to be announced

What the Press is Saying
Take some time to read what the press has said about the Vermont Challenge.

Stratton MagazineAdventure Cyclists Magazine

Vermont SKI+RIDE, Vermont's Mountain Sports & Life named the Vermont Challenge one of its "8 Rides of Your Life." Read about it here:

VT SKI+RIDE Headline
The way up and the way down are not, just not, one and the same.
That's all I can think as I push/pull/cajole the wheels into one more rotation, then another. I stand, putting my full weight on the pedals. Think positive, I coach myself. I'm grateful .. grunt.. for the cool green tunnel of hardwoods shading the road. Grateful ..groan..for the packet of maple syrup from the last aid station, liquid energy. I'm grateful for the six guys who let me draft for the last 10 miles. Grateful for the swimming hole ahead that's going to be deliciously cool.
Then, the trees open up. There is light. The road crests at the gap. Below, a toy landscape of farms with red barns spreads out. Patches of green fields are dotted with miniature black and white cows. A white spire rises through trees in the distance. I pause to take a swig of water, shift into my largest gear and then let go, screaming down the other side, taking the S turns like a ski racer on a GS course.
By far the best way to see Vermont, I'm convinced, is on a century ride or organized group ride. In the past few years, a host of new rides have sprung up with events such as the Vermont Challenge, Farm to Fork Fondo, and the Vermont Gran Fondo, making the national Top 10 lists. Others, like the Tour De Kingdom, are lesser-known gems that will show you roads you never knew existed.
Yes, you pay an entry fee but you get a sag wagon, in case you have a mechanical issue. And then there are the aid stations. Since this is Vermont, instead of GU and Budweiser, there might be PB&J sandwiches on slabs of homemade bread (Vermont Challenge) or woodfired pizza with farm-fresh toppings (Farm to Fork Fondo). After parties? In Vermont, you don't bring the beer to the party, you take the party to the beer. Three rides start and finish at Harpoon Brewery, Long Trail Brewery and Woodchuck Hard Cider this year.
There is an organized ride somewhere in the state nearly every week, here is one of our favorite loops, in August.
VT SKI+RIDE Headline
Heading out from Stratton on Day 3 of the Vermont Challenge. Photo by Hubert Schriebl

The Vermont Challenge: Stratton to Okemo and back, Aug. 17-20
If you took the best aspects of a multi-day guided bike tour (sag wagons, lunch stops, dinners sharing stories of the day over a craft brew) and combined it with four days of the semi-competitive (read: bragging rights only) fun of a century ride, you'd get the Vermont Challenge.
Stratton skier John Sohikian dreamed up the Vermont Challenge as way to showcase some of the best riding routes in southern Vemont. The four-day event heads along the valley between Manchester to Dorset, before climbing into the mountains around Stratton and sending riders on a 107-mile fondo toward Okemo.
Of course, you don't have to do all four days of rides. You can sign up for shorter routes each day (starting at 23 miles). You can stop where you want (last year's favorite rest stop was at Wilcox Dairy, which makes a killer salted caramel ice cream). You can join in the group kickoff dinners at the Taconic Hotel in Manchester or eat on your own. You can do just the Valley Days (Day 1-2) or just the Mountain Days (Day 3-4). In 2016, the fifth running of the Challenge the ride raised $9,200 for local charities and $10,000 the year before.
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460 Stratton Gate Rd
PO Box 203, Jamaica VT 05343
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