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This two day tour includes truly one epic day of cycling. Experience the beauty and grandeur of cycling over (M)Middlebury, (L)Lincoln (steepest 1 mile in America),(AP) Appalachian, (Rx)Roxbury, (R)Rochester and (B)Brandon gaps. The first day encompasses a 25-30 mile warm-up toward Shoreham. The second day is the main event, and covers 135 miles, 12,000 feet of climbing and 8-9 hours in the saddle.  We can modify this tour to include any even numbers of gaps, 4 gap(LAMB) or 2 gap (MAP or MB), the choice is yours depending on your fitness level or the time of year.

Dinner options include inn-style dining at one of many fine establishments throughout the region.


Day One: Welcome to the Gaps

After checking in at our accomadations we head out for a 25-30 mile warm up ride toward Shoreham and loop back to Lake Dunmore thru West Salisbury and back to Middlebury.

The theme for today is all about relaxation and preparation for tomorrow’s ride. Proper nutrition, hydration and rest is imperative as we will burn 4,500-5,000 calories throughout the day in the saddle; don’t forget your chamois butter/cream! You will require 2 large water bottles per hour and lots of food. Stock up on your bars, gels, and any other supplements you might need!

Meals: Light Lunch / Dinner, Big and Hearty
Accomplished: 21 miles / 34 km

Day Two: The main event;  6 gaps

After consuming a hearty breakfast with plenty of carbohydrates to fuel our bodies we head out to conquer the epic 6-gaps. The key to a successful ride is to “pace it”. We start by climbing the West side of Middlebury gap. Turn left onto Route 100 and tackle the infamous Lincoln gap next. The last 1 mile is nasty, some reports are between 18-24% of consistent grade. “Pace It.” After this, the worst is over, and it’s on to the towns of Lincoln and Rocky Dale via Route 116 to South Starksboro and then up to Appalachian gap via route 17. “You are halfway there.” A nice descent to Waitsfield and Warren and it’s up Roxbury gap on Route 12A. “This gap is quite tough at the summit; don’t underestimate it.” After a fairly long (10-12 mile) flat, low trafficked road it is time for the fifth hill,Rochester gap, don’t push this one, “Pace it”, you will need all the energy you can muster for the last and easiest gap, Brandon gap on Route 73, which rewards you with a spectacular descent into the village of Forest Dale and then on into Lake Dunmore, where the ride ends.

Congratulations, you’ve completed the epic 6 Gap ride, with the steepest 1 mile in America. After a shower and an opportunity to lie down and rest your weary legs, it’s off to celebrate your achievement at a local steakhouse where you can enjoy all the refreshing Vermont farm fresh chocolate milk you can drink and the best post ride burger ever.

Meals: Breakfast/ Lunch/ Dinner
Destinations: Middlebury, Ripton, Hancock, Warren, Lincoln, Rocky Dale, Waitsfield, Roxbury, Randolph, Bethel,  Rochester and Brandon
Accomplished: 135 miles 6 gap  / 85 miles 4 gap/ 58 miles 2 gap


  • Satisfaction of completing one of the toughest 1 day rides anywhere
  • Superb pre and post ride dinners at American Flatbread and Shoreham Inn pub or Fire and Ice restaurants
  • Lasting friendships with like minded cyclists
  • Memories that will last a lifetime

What’s Included

  • FTA schwag bag including , water bottles, pint beer glass, newly designed FTA t-shirt,
  • Top of the line carbon road bike or aluminum hybrid bicycle at no additional fee
  • All breakfasts, all lunches,2 gourmet dinners, Après Velo cocktails, and nutritious snacks
  • 2 nights lodging with all meals and on ride beverages and snacks