2026 marks the 39th Anniversary of the Great River Ride. Over the years the GRR has been recognized by the League of American Bicyclists (LAB) and Bicycling Magazine as one of the top century rides in America. A variety of routes are offered to match the skill levels of all participants. Event proceeds will benefit the programs of the Friends of the Columbia Greenway Rail Trail (FOCGRT), a 501 3c nonprofit organization.
Staffed refreshment stops along the ride as well as a post-ride buffet with live entertainment from 2:00 PM to 5:30 PM.
You will encounter knee-popping hills, breathtaking views, awesome descents, and gorgeous fall foliage as you tour the hilltowns of the Eastern Berkshires. Add in miles of stone walls, waterfalls, plenty of New England white churches, loads of colonial homes, historic keystone arches, a wild and scenic river, and did I mention hills. But thats not all, we've got rest stops staffed with friendly cyclists and snacks, including our famous "Baked Potato" stop.
The Westfield River, the Great River in the river ride, is a federally designated Wild and Scenic River. The GRR wanders the course of this scenic river to give you a unique cycling experience. For 2026 we're using most of the original route, thanks to Mass Highways repaving projects. The Century will actually total 108 miles with bailout options and we've got the original 25 mile downhill run (mostly) to the finish.
The GRR Gravel Route is a mix of pavement, gravel, dirt and seasonal roads that we’ve enjoyed fall riding on for over 50 years. The 72 mile route is 40% unpaved.. The route will take you through the remote Knightville Basin and Chesterfield Gorge with stunning vistas along the East Branch of the Westfield River. You’ll pass through the Knightville Meadows, the Rainbow Pool, the Little Gorge and the Chesterfield Gorge on your ride. Most climbs are paved but Thayer Rd. is a moderately difficult climb of 1.4 miles on dirt ranging from 10% to 7%. A long descent to River Rd. follows a seasonal road with some steep downgrades. At River Rd. you will have a choice of the final gravel climb up Maynard Rd. or the bailout paved climb up East River Hill to the Spud stop at the Chester Hill Church. Gravel/Dirt sections will not be monitored by SAG vehicles and Cell Phone coverage is limited. Be prepared to handle mechanical problems,and flats. Several miles of the route follows a gated road closed to motor vehicles. We recommend teaming up with other riders on these sections. Tire widths of 38mm or wider are recommended. Fallen leaves will hide loose and bony surfaces, so caution on descents is advised.
Our Winery Ride uses the Columbia Greenway Rail Trail and New Haven/Northampton Canal Trail for a flat 28 mile ride with a stop at the Brignole Vineyard for snacks (wine will be available for purchase).
Our 42 mile road route includes one moderate climb up the Granville Gorge with a mid ride rest stop at the Brignole Vineyard. At the vineyard you will have the choice of returning on the road (rolling terrain) or using the rail trail (flat).
Family Friendly - Free entry for children 15 & under riding with a registered adult.