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Vermont Challenge Tours:

Our roads are calling.

Vermont’s Top Rated 4-Day Tour

August 12-15, 2021
The Final Year!
Yes, it's true. This is our final year of presenting The Tours of the Vermont Challenge. This is your last chance to get in on the fun and excitement. The Tour will offer, for one last time, experienced leader-lead scenic rides at a fraction of package tours. Our 2021 tour is limited to 100 riders, so 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.

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Vermont Challenge for 2021

After last year's limited field, we are excited to open up the Tour to 100 riders thhis year – our final year. We hope you are as excited as we are to get out to ride and have fun after the lock downs of last year!
We revised our starting locations last year, which was a huge success, so those locations will stay the same. We'll again offer routes through some of the most picturesque roads found anywhere. We will continue our approach of breaking down the field into rider led groups.
The Vermont Challenge is not a race, it's a friendly social tour that offers a competitive edge and challenge. If you're a cyclist that rides frequently and enjoys new challenges, riding new terrain and meeting other like-minded riders, then the Vermont Challenge is a MUST ride for you. Come join us and celebrate 2021: The year of re-opening!

Overall Logistics
  • 4 consecutive days of riding
  • Limit total registrations to 100 riders
  • Will offer a water bottle, tech T and a jersey & shorts/bibs. You MUST register by 6/18 to secure a kit. No exceptions.
  • Each rider's check-in kit/bag will be pre-stuffed for distribution.
  • We will offer 4 lunches and 2 group dinners (locations to be announced)

Daily Logistics
  • We'll break up into 3 lengths of rides per day that we'll break down into 2 -3 average pace levels per length
  • Each of our 3 daily routes will have its own support/refueling vehicle.
  • Will provide a list of all services on all routes. These files should be uploaded to your phone.
  • Will have a designated stop on each route

Cycling through Manchester Center, Vermont Challenge.

Vermont Challenge Sponsors

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What the Press is Saying
Take some time to read what they are saying. Just click on the magazine covers or links below.

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.

Our roads are calling.

Three beautiful routes each day over four days of riding.

The Tours of the Vermont Challenge are offering three routes each day. And each day's routes are different than the last. There will be two groups for each route all led by seasoned ride leaders providing you with information about the area and stopping along the way for snacks at local markets and country stores. Be sure to explore the website to see what's new for 2021.

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What Cyclists Are Saying
Here's what riders have said about the Vermont Challenge:

"Just a well-run event, great volunteers, well stocked rest stops, real food at the end, nice countryside, and good ride support. Nice job – the effort you put into it shows."    – HAVERFORD, CT
"The routes were gorgeous, covering some of the most beautiful territory of the great state of Vermont. The food stops were fully stocked with smiling and friendly volunteers who encouraged and cheered us on. The volunteers were moved from one location to the next so we often got to see the same faces multiple times, which was fun! The meals, cookouts, etc. were also impeccably planned. It was obvious how much upfront work goes into the event – as well as during and after. It seemed like they had four times the volunteers they actually did!"    – STAMFORD, CT
"This was the best tour I have ever ridden. Food, routes, people. The volunteers were great"    – FOXBORO, MA
"The CHALLENGE was the best part! I had butterflies in my stomach until I got to the top of Brandon Pass, worrying I'd bonk – but WHAT a feeling of accomplishment! There was impeccable logistical organization and a terrific choice of roads. It was really an outstanding event from start to finish. Kudos to all who organized and volunteered!"    – COBOURG, ON, CANADA
"The Vermont Challenge has one overwhelming advantage: It offers a beautiful countryside on quiet roads."    – HARTSDALE, NY
"A GREAT event! A good time was had by all... Looking forward to next year. KUDOS to everyone who worked hard to make this such an enjoyable event!"    – NEW BRITAIN, CT
"Thanks so much for the VT Challenge – truly an awesome event for an important cause. I must say this was one of the BEST organized and professionally produced events I have ever been involved with. I have been cycling at a high level for a long time and you hit it out of the park to say the least. I very much look forward to next year's VT Challenge and I will be sure to pull in additional riders."    – TINTON FALLS, NJ

Sharing a Meal the Vermont Challenge.

4 Days of Awesome Group-Led Rides

The Vermont Challenge is offering four days of riding through the picturesque countryside of Vermont. The following is the listing of rides for The Vermont Challenge from August 12–15, 2021.

Day 1, Thursday -starts out of Dana Thompson Park, 340 Recreation Park Rd, Manchester Center, VT.
Day 2, Friday - will start from the Mettawee Community School, 5788 VT-153, West Pawlet, VT.

Day 3,Saturday - medium and long routes out of Stratton Mountain Resort, 5 Village Lodge Rd, Stratton Mountain, VT. Saturday short route will be out of Bondville Community Center, 1 River Road & Route 30, Winhall VT.
Day 4, Sunday - route out of Long Trail School, 1045 Kirby Hollow Rd, Dorset, VT.

All stages start and finish at their respective locations for that day.

Detailed routes will be sent to all registered riders in advance of the event.

2021 Tour Pricing

4-day Grand Tour 8/12-15 $699
4 Bike Tours (Thursday through Sunday)
2 Dinners per Rider*
4 Farm to Table Lunches* (Thursday through Sunday)
Tour Cycling Jersey & Short/Bibs
Tech T-Shirt
Water Bottle
Goodie Bag
Tech Support during Rides
*Locations to be announced

Vermont Challenge Tour Riders
DAY 1:
Bucolic is the best description for these routes that head south and west from Manchester Center. You'll to be cycling across famed covered bridges and through rural villages like Pawlet and Rupert both situated in the valleys between the Green and Taconic Mountains.
There is certainly no shortage of mountain, farm and river valley views as you ride along these beautiful Vermont roads. The groups will have a Farm to Table Lunch at Dana Thompson Park at the end of the Day 1's tours.
Short Route - 37 miles
1,669 ft. ascent
Medium Route - 49.1 miles
1,992 ft. ascent
Long Route - 69.6 miles
3,819 ft. ascent
Tour Event Number
Vermont Challenge Tour Riders
DAY 2:
Our second day of the Vermont Challenge Tours starts in various locations and heads north and features more beautiful terrain through gentle rises and sloping valley areas, where farms and fields of corn are not an unusual sight.
The picturesque town of Middletown Springs is the most northern point on the longest route and defined by the encircling mountains. You'll also enjoy a snack stop at Sissy's Bakery: a stop not to be missed! As we head back, you'll pass through beautiful farmlands.
All groups will have a Farm to Table Lunch waiting for them at Dana Thompson Park at the end of Day 2's tours. The short and medium riders with drive down to the park.
Short Route - 36.3 miles
2,280 ft. ascent
Medium Route - 54.2 miles
3,125 ft. ascent
Long Route - 67.4 miles
3,905 ft. ascent
Tour Event Number
Vermont Challenge Tour Riders
DAY 3:
Our third day Medium and Long tours start/end at Stratton Mountain's base resort at 2100 ft., the highest peak of the Southern Greens. The short tours start/end at the bottom of the mountain. We follow the river valleys to start and then cross the Green Mountains through mountain passes. These passes offer gradual sustained climbs, so you can get into your own rhythm.
We'll stop at a Farmer's Market in Londonderry offering you the opportunity to shop and have your items brought back to you at lunch. Longer routes also stop at the Vermont Country Store for a maple creamy. We finish Day 3's tours with a BBQ lunch at the green behind Stratton's base lodge.
Short Route - 32.5 miles
Depart: Bondville Community Center
Start Time: 9:00 am
2,522 ft. ascent
Medium Route - 54.8 miles
Depart: Stratton Village Square
Start Time: 8:00 am
4,400 ft. ascent
Long Route - 99.3 miles
Depart: Stratton Village Square
Start Time: 7:00 am
7,969 ft. ascent
Tour Event Number
Vermont Challenge Tour Riders
DAY 4:
For Day 4, we'll be traveling on some familiar roads but from a different perspective. The long route will travel north and then east across toward Mt Tabor before turning south heading back. Our medium route utilizes two beautiful valleys with a climb over to Danby that connect the two. The valleys offer beauty farm views surrounded by the mountains.
Our short route heads south entering the valleys from a different direction replete with farm animals and beautiful landscapes.
There will be stops at the Dorset Union Store, Sherman Market, Wayside Market and Village Peddler, depending upon which ride you're on. These are amazingly quaint country stores. Day 4's lunch will be held in Manchester at the Battenkill Bike Shop.
Short Route - 35.5 miles
1,346 ft. ascent
Medium Route - 48.2 miles
2,177 ft. ascent
Long Route - 67.6 miles
3,756 ft. ascent
Tour Event Number


Riding the Vermont Challenge.

The Vermont Challenge mission is to provide the ultimate riding experience while striking a balance between the touring rider and the more serious cyclist. Offering a variety of scenic destinations that provide an authentic Vermont experience is our number one goal.

460 Stratton Gate Rd
PO Box 203, Jamaica VT 05343

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