Routes

Riders can choose to ride 8 miles, 25 miles, or 50 miles on some of the best roads and off-street paths in Eastern Mass.  All of the routes head west-southwest from Jamaica Plain with 'cutoffs' for the different route options. Just like last year, all rider bibs will have a QR code for each route, which can be scanned via smartphone to quickly pull up a link to any route.

Whil we don't have the final routes for 2027 quite yet, you can see last year's routes on Ride With GPS. We don't anticipate making many changes from these routes, giving you a good idea of what to expect for 2027. View the 2026 route collection here.

 

8 Mile

Emerald Necklace

The Emerald Necklace route is perfect for the whole family, taking advantage of cycling paths wherever possible in Franklin Park, along the Southwest Corridor Park, and near Jamaica Pond.

The rest stop in Franklin Park is located halfway through the route with easy access to a playground. 

View the 2026 10 Mile Emerald Necklace route.

25 Mile

To the West(on) Reaches

This hilly route is perfect for cyclists who don’t want to spend all day riding but still want to get a great workout in.

This route takes riders through Roslindale, West Roxbury, Newton, and Needham and will include a scenic, riverside rest stop where riders can fuel up before riding back to the after party in Jamaica Plain.

View the 2026 25 Mile route here.

50 Mile

A Trip to the Farm

After splitting off from the 25 Mile route outside of the city, the 50 Mile route shines as riders pass through beautiful landscapes in Lincoln, Concord, and Wayland.

This route utilizes well-maintained, quiet roads as it weaves past conservation land, picturesque farms, and historic homes.

Fuel up at two scenic rest stops: one alongside the Charles River in Wellesley, the other at a beautiful farm in Lincoln.

View the 2026 50 mile route here.