This route travels from North Canaan, CT to October Mountain State Forest in Massachusetts. Expect a spectacular gravel ride in the Berkshires region that includes all of the dirt from F2G2 (Fall Foliage Gravel Grinder) and a lot more. It should make for a beautiful day of riding, regardless of the season! Strava estimates about 9500ft of climbing, which is a better estimate than RWGPS's estimate of 8400 ft. Expect ~65% dirt roads by distance, but probably 75% dirt by riding time. Overall, a gorgeous route with a mix of deep woods, open vistas, smooth dirt, rough dirt, and a bit of double-track and jeep-road adventure mixed in. Expect a fun day of exploration!
CAUTION: The descent on Brace Road is very treacherous. It starts off looking somewhat rough, but not too bad, but quickly becomes washed out and destroyed. Take it slow!
REFUELING: Mile 37 in Lee, MA. Make sure to fully refuel! There aren't many businesses along the route between mile 37 and mile 84 (Sheffield, MA). That's 47 miles and 4000ft of climbing. Bring lots of food and water.
BAILOUT: At mile 75, it is possible to return directly to the start for an 85-mile day instead of the full 100. Useful if anybody runs out of steam in the latter half of the ride.
Bailout Route: ridewithgps.com/routes/48256363
THIS ROUTE IS BEST DURING TIMES OF DRY WEATHER: The weather had been dry before our ride here, but even so, a few of the "roads" (really trails) were just barely beyond mud in terms of texture. Others were obviously places that would turn into stream beds after any significant rain event.