Four rides to choose from

We encourage bicyclists of all ages and abilities to ride with us!

Choose your ride 

Each year we have riders as young as 2 and as old as the hills (as old as the 75 year-old hills that is). We'll be a mix of training racers in spandex for speed, around-town commuters in everyday clothes, teams of friends, serious fitness riders, new cyclists, kids in trailers, on bike seats, and on trail-a-bikes. Ride at your own pace! Our following mechanics and vehicles won't let you get lost or left alone out on the route.

All rides

  • Require pre-registration
  • Start and end in the big field in front of the Stony Brook T stop (Orange Line) at Boylston and Amory Streets, Jamaica Plain MA 02130
  • Are supported by ride marshals at the head and tail of the ride as well as following vehicles with tools and first aid. 

The 15 mile ride

A great ride for cyclists of all abilities, including families with children! We ride south through JP on the Pierre Lallement Bike Path; pass by the Arnold Arboretum and make a moderate climb on Bellevue Hill into the woods of the Stony Brook Reservation. There is one rest stop at Kelly Field Playground in Hyde Park.  We continue riding through Hyde Park into Mattapan, then head into Franklin Park going back to the starting point in the Southwest Corridor Park, where you'll roll into the Green Roots Festival!  Some urban safe-riding skills will be necessary.

The 25 mile ride

For a more challenging ride, the 25 mile ride follows the path of the 15 mile ride into the Stony Brook Reservation then veers off to climb into the Blue Hills going through Milton & Canton. There is one rest stop at Houghton's Pond in the Blue Hills Reservation. The ride continues through East Milton overlooking the Neponset River Reservation, going through Dorchester Lower Mills into Mattapan & Franklin Park. The ride ends back at the starting point, in the Southwest Corridor Park, where you'll roll into the Green Roots Festival!  Urban riding skills necessary.

The 40 mile ride 

We've designed this ride to be as scenic as possible. It heads straight out west to the Farm Pond area in Dover and Sherborn. Experienced roadies from all over Boston know this area as one of the best places to find smooth roads and beautiful views. At the midpoint of the route you'll have the pleasure of visiting the Peace Abbey for a quick snack and water refill. Along the way you'll ride by sweeping fields, babbling creeks, and shady groves. The route will take you back to the Green Roots Festival in Jamaica Plain via the same path as the longer 65 mile ride.

The 65 Mile Ride

Perfect for the avid cyclist, this gorgeous ride goes west from Jamaica Plain through Newton and Weston, and then north to the first rest stop at a farm run by The Food Project in beautiful Lincoln. turning South through Wayland and Natick, the second rest stop is at the Peace Abbey in Sherborn. The final stretch runs through Dover, Needham, and Brookline, rolling right back to the starting point in Jamaica Plain and into the Green Roots Festival.