Vermont > Four Gaps Weekend Tour – NEW!

3-DAY / 2-NIGHT BIKE TOUR – $795
October 4-6, 2019

This new tour gives you the chance to test your legs on the challenging passes over several gorgeous Vermont ridges. You may have heard of (or dreamed of completing) the famous Four Gaps “LAMB” ride. This tour cycles the Green Mountain passes of Lincoln (L), Appalachian (A), Middlebury (M) and Brandon (B).

You stay at a comfortable, historic 1827 inn that features a hearty breakfast each morning. Our van carries snacks, water and picnic supplies to fuel your climbs. And our leaders are there to cheer you on — or provide basic repairs, if needed.

Feel a sense of accomplishment as you tackle each hill and enjoy the exhilaration of descending down the other side. Then high five your group members when you arrive at the inn. As a reward, dig into sumptuous meals that you’ve truly earned.

Four Gaps Weekend Itinerary


Enjoy three epic days of riding Vermont’s high gaps, centered around the historic Middlebury Inn.

DAY ONE | Distance: 15 miles  |  Terrain: Easier 
Settle into your room at the inn on Friday, meet your leaders, and get your bike set up and ready for an initial checkout ride. Then head out along the base of the mountains to Bristol, along the same route where we begin on Saturday. This gives you familiarity with the roads and bikes as we prepare for the next two days of longer riding.

DAY TWO  |  Distance: 60 miles  |  Terrain: Advanced  
Spend Saturday on the two northern gaps — Appalachian and Lincoln. Climb Lincoln first, but from the slightly easier west side. Rollers and a gradual climb give way to a final mile of 10-15% grade. Descend from Lincoln to the east, and head north and then back over the mountains through Appalachian Gap. The final two miles are again the steepest, but more in the 8–10% range. Enjoy the final descent and valley ride back to Middlebury — along with the dinner celebration for completing the hardest day of the trip!

DAY THREE | Distance: 54 miles |  Terrain: Advanced
Sunday brings another epic day of gap climbing — to Middlebury Gap. The longest sustained climb of the weekend is a good warm up for the day, with gradients mostly in the 5–8% range. After one more descent to the east, head up to Brandon Gap, the final climb of the weekend. We save the shorter climb to the end, and you can congratulate yourself as you descend into the valley and ride back to the Middlebury Inn.

Four Gaps Weekend


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


October 4-6, 2019: $795
Reserve with $200 deposit

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

Single Supplement Fee for Private Room: $200 

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.


With relaxing comfort in the heart of the Champlain Valley, the Middlebury Inn welcomes you with restored rooms and Victorian accents. This hotel has been providing lodging since 1827 and is considered one of the five oldest hotels in the U.S.


What’s Included

2 nights lodging, 2 breakfasts, 2 dinners, 2 lunches, experienced leaders, van support, use of bicycle and helmet.


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.