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The Solstice Ride

June 18 – 20, 2021

An epic adventure consisting of a three-day ride from Westport, CT to Montreal QB with support during the ride as well as organized return transportation, making this an obtainable summer goal!



Completing this ride takes SAG support, a team effort and superb individual fitness. Crossing four states and an international border while traversing diverse terrain with unpredictable weather will challenge you at every pedal stroke. Each of the three days offer unique challenges, terrain and scenery. Read a recap of the 2019 event here

Overall the ride was outstanding! Well organized, fantastic route and a great group of people. It proved to be a real challenge with a great sense of accomplishment. You definitely helped me move my boundaries 😊



  • 130+ miles / day with a half-way rest stop each day
  • Day 1: Westport, CT to Williamstown, MA – 135 Miles 8300’ of Elevation
  • Day 2: Williamstown, MA to Middlebury, VT – 137 Miles 9500’ of Elevation
  • Day 3: Middlebury, VT to Montreal, QB – 144 Miles 5200’ of Elevation
  • Backcountry roads, a small sections of gravel and moderate climbing
  • SAG support for the entirety of the trip
  • SAG transports overnight bag to each hotel
  • A major boost of endurance well in advance of intense summer riding/racing
  • Expierence an incredible cycling adventure


The trip was freakin fantastic. I keep reflecting back on the trip. I loved everything about it.

Alex Carrio

The Solstice Ride was one of those experiences that you know is going to be great on so many levels. Getting pushed physically, spending quality time with a new group of men and women cut from the same cloth, and riding the road less travelled was just what I needed. Sherpa knows how to design and execute exceptional experiences. Get one

Adam Pemberton

I really appreciate all the planning, motivational emails, in-ride guidance, and teamwork that went into making this journey happen. I feel lucky to have been part of this excellent group, and everything from the challenging route selection, the nightly accommodations, food stops, and transportation logistics were spot on.

Pete Kim

Great experience that will last forever! ☝️ A tough one but a must do.

Paula Valderrama

Great trip, enjoyed and suffered at the same time.

Jack Mullen

Convinced you can do this?


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