Vermont > Two Centuries Weekend
Bike Tour

July 19-21, 2019 

Are you a seasoned long-distance rider looking to test your legs? Vermont is full of fantastic cycling, and one of the best ways to see it is on a challenging century bike ride of 100+ miles. The only thing better is TWO centuries in one weekend!

This new tour features a Saturday ride from the northern border of Vermont at Jay Peak to Middlebury and a Sunday ride from Middlebury through western Vermont to Manchester, VT, in the southwest corner of the state. We pick up the group in Manchester on Friday at noon and provide a fully van-supported weekend for you to take a big bite out of Vermont’s back roads.

Be one of the first to try out this fun and exhilarating route. There are gorgeous views and delicious food and drink to power you along the way. Don’t miss this Vermont Two Centuries Weekend!


Vermont Two Centuries
Bike Tour Itinerary

Enjoy exceptional rural scenery, forests, lakes, rivers and farmland while cycling from northernmost Vermont near the Canadian border … to the southwest corner of the state. Rest and refresh yourself along the way and resupply yourself at country stores, local restaurants and/or with snacks and water from our support van.

DAY ONE  | Arrival Day | Jay Peak Resort
On Friday, you meet at the Park-and-Ride in Manchester Vermont, and we shuttle you and your bike to Jay Peak Resort in the far northern reaches of the state. We provide road bikes for anyone who doesn’t bring their own, and we have a few extra road bikes along in case of major mechanical issues for any riders. Friday night you feast on a BBQ dinner slopeside on Jay Peak, with an option to take an aerial tram ride up the mountain and watch the sunset over Northern Vermont and Quebec.

DAY TWO  |  Distance: 100 miles  |  Terrain: Intermediate to Advanced | Middlebury Courtyard by Marriott
On Saturday, you begin the ride by descending from Jay Peak and head south and west around Vermont’s highest peak, Mount Mansfield. The town of Underhill is at mile 45 and provides a chance for a break. Then head on to Middlebury, Vermont, and the end of today’s century at The Otter Creek Brewery. Rest up at Middlebury’s Courtyard by Marriott, then get ready to head south again for another 100 miles on Sunday.

DAY THREE  |  Distance: 100 miles  |  Terrain: Intermediate to Advanced | Departure Day
Sunday’s century ride continues down the western side of the Green Mountains and winds through the farms and lakes of rural Vermont. Arrive in Dorset for a toast to your big accomplishment … a whole weekend of riding! We will have a van along with snacks and water for everyone, along with mechanical and SAG support.

Vermont Two Centuries Weekend Bike Tour


Make your reservation with confidence. Your tour is completely 100% refundable up to 60 days before the tour date.


July 19-21, 2019: $695
Reserve with $300 deposit

Final payment due 60 days prior to your tour (personal check, Visa, MasterCard, American Express or Discover)

Single Supplement Fee for Private Room: $250

Cancellations: If you cancel your tour reservation, your cancellation fee will be determined as follows:

  • If you cancel 60 or more days prior to the start of your tour, there is no cancellation fee.
  • If you cancel between 45 and 59 days prior to the start of your tour, you will forfeit 50% of all tour payments.
  • If you cancel between 0 and 44 days prior to the start of your tour, all tour payments will be forfeited.


The Jay Peak Resort has a wide variety of restaurants, activities and pubs. We enjoy a BBQ dinner with an option to ride a tram to the top of the mountain for views of the valley.



The Courtyard Middlebury by Marriott features a Bistro, snack bar and comfortable rooms. We’ll get a good night’s rest here and prepare for the second century ride.



What’s Included

2 nights of lodging; 2 breakfasts and 1 dinner; transfer from Manchester to Jay Peak Resort; free use of bicycle and helmet if you like; detailed maps and itineraries; experienced guides; full van support; snacks and water in the van.


We are happy to provide you with a bike to use at no charge. Our bikes come equipped with a front handlebar bag, rear carrier, water bottle, mirror and flat pedals. Pedal cages and soft gel seat covers are available on request. We are also happy to put your own clipless pedals (pedals that attach to your biking shoes) and seat on your bike if you wish. Specific details and styles of bikes available in each location are indicated under each photograph below. The make of bikes provided varies by location.

A collection of photos from a variety of our Vermont tours.