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Our Roads Are Calling

The Shires Tours

August 15 – 18, 2024

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. We are designing all new routes to switch it up form past tours. The tour includes all lunches and dinners. Limited to a approx. 35-40 riders.

Profiles of the Tours

Vermont License Plate
The Vermont Challenge in 2024 offers routes that are led by ride leaders, unlike the one's on our route-arrowed, leaderless tours. These routes are designed to specifically meet the needs of those wishing to see and enjoy Vermont – all from the saddle of their bikes.

Setting Expectations

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. These routes are designed for riders who ride a fairly regular basis and have ridden 30 or more miles on multiple days.

The Shires Tour
  • 3 consecutive days of riding: Friday, Saturday and Sunday
  • Limit total registrations to 40 riders
  • Includes all lunches and dinners
  • Route lengths/pace – two lengths to choose from: Mid 30s and mid 50's lengths daily, broken into two average paces
  • SAG Support
  • Jersey (must register by 4/15 to get the jersey)
  • Tech Shirt
  • VTC Coffee Mug
  • Early Bird Pricing (see below)
  • Will provide a list of all services on all routes. These files should be uploaded to your phone or navigation device
  • We'll stop at key locations like Country Stores etc.

Shires Tour Pricing
3-day tour Aug 15-18 – $599 through April 15
From April 16 until tour fills – $649
Excludes lodging*
*Suggested lodging below

This Year's Tour Jersey
2024 Vermont Challenge Jersey
The jersey for 2024 was an all new design that features elements of The Shires Tours. You will have to register for the Tour by April 15th to ensure getting a jersey.
The front and back design elements, with it's pine trees, rolling hills and valleys, and covered bridge, all represents the Shires Tour to be held this August and where all rides are ridden in the Green Mountains Region of Vermont.
To see a large image of the jersey, click here or on the image itself.
Jerseys are gender specific manufacturer by Agile Sportswear (formally named Ascend Sportswear). The are two different cuts to choose from. One is Sport Cut, which falls between the tight fitting slim/race style and the looser fitting relaxed cut. Sport Cut provides a close to the body fit without compressing. The second is Relaxed Cut, which is a looser fitting more roomier fit Sizes run from XS – 4XL. When booking, please specify gender, size and cut.
This will be a custom order so please make sure you double check your fit and size.
To help you select the right size and cut, we have also included a Agile Sportswear Guide so you can double check your size. We have also included a Agile Features Chart for you can learn more about the Elevate jersey.
The Shires Lodging
As part of the planning of The Shires Tours of the Vermont Challenge, budget concerns were factor into our new format for pricing. The Vermont Challenge lets its Shire riders choose for themselves where they wish to lodge so they can control their own budgets. So there are no lodging fees added into that tour package price. The following are some suggested lodging.
Palmer House Logo
Manchester: Palmer House
5383 Main St, Manchester Center, VT 05255   802-362-3600
Our exclusive Lodging Partner in Manchester is the Palmer House Resort, Ascend Hotel Collection. The Palmer House Resort is centrally located with access to all Vermont Challenge starting points and provides breathtaking mountain views, oversized yet cozy overnight accommodations, unique year-round amenities and an exclusive rate discount with complimentary breakfast to all Vermont Challenge riders. To book with Palmer House, click here.
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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