Registration Opens January 5th, 2027. 9am (EST)
Intro: First and foremost, please read our Cancellation Policy. Also, this is technically a "digital download" purchase as my website either needs physical inventory, or its a digital download (a tour is neither). Feel free to ignore download link that will be sent.
Tour Description: Our 2027 New England 5-State Tour (formally know as our "Berkshires Tour") is a 8 day, 7 night self-supported bike camping trip with a Rest Day built in to Day 4. Starting at Copake Falls Campground and ending at the Wassaic (NY) Train Station, the route is a clockwise loop that covers 5 states (NY, MA, VT, NH, CT).
The name "Berkshires Tour" (this tour's inaugural name in 2026) was bit misleading....hence the new name for 2027.
Ride across five New England states on one unforgettable self-supported bike camping adventure. Our 2027 New England 5-State Tour travels through New York, Massachusetts, Vermont, New Hampshire and Connecticut, linking quiet backroads, beautiful mountain landscapes, small New England towns and some of our favorite campsites into an epic week on two wheels.
Over seven days of riding—with a well-earned rest day in Jamaica, Vermont—you’ll experience everything from the Berkshires and southern Vermont to a quick spin through New Hampshire before working your way south through Massachusetts and Connecticut and finishing at the Wassaic train station. It’s a big, rewarding journey designed for riders who want more than just a bike ride: a week of traveling entirely by bike, camping each night, swimming along the way, and sharing the kind of adventure you’ll still be talking about long after you get home.
We ran this tour for the first time in 2026, and it was hard. For 2027, we have split the hardest day into 2, and added a rest day to bring this trip in line with our other longer adventures in terms of challenge level, and reduced elevation on a few key days.
Tour Rating: In-Progress
Years Run: 2026
Group Size: 24
GPS Maps: Berkshires Tour Maps
Interactive Map: Berkshires Tour Interactive Map
Ride Sheet: 2027 Berkshires Tour Example Ride Sheet
2027 Itinerary:
Day 0: Saturday, June 19. This is a travel day, if required.
Day 1: Sunday, June 20 Copake Falls, NY to Pittsfield, MA (40 miles)
Day 2: Monday, June 21. Pittsfield, MA to Wilmington, VT (51 miles)
Day 3: Tuesday, June 22. Wilmington, VT to Jamaica, VT (26 miles)
Day 4: Wednesday, June 23. Rest Day, Jamaica, VT
Day 5: Thursday, June 24. Jamaica, VT to Brattleboro, VT (and a little NH)(40 miles)
Day 6: Friday, June 25. Brattleboro, VT to Goshen, MA (52 miles)
Day 7: Saturday, June 26. Goshen, MA to Riverton, CT (63 miles)
Day 8: Sunday, June 27. Riverton, CT to Wassaic, NY (44 miles)
See Ride Tables (with elevation and mileage)
Logistics: The interesting thing about the logistics on this Tour is that its the only 718 Tour that starts in a campground. The idea is that one would travel on Day 0 (Sat, June 19), camp with the group overnight at Copake Falls, and be ready to go on Day 1 (Sun, June 20). In 2026, our Day 1 was the ride from the train station to Copake Falls, which I felt was an inefficient use of a day.
On Day 0, people will either take the Metro-North train up to Wassaic and then ride the 23 mile rail trail ride to the campsite at Copake Falls, or drive. If you are looking to drive/carpool, you can leave your car in the long-term parking lot at the Wassaic Train Station, and then do the 23 mile ride up to the campsite at Copake Falls. Or, you can just do your thing at meet us on Day 1 however you'd like.
If you are registering for this trip, you are highly encouraged make your travel plans soon thereafter and not wait until a week before the tour.
Links: