Quick ride by bicycle from Brookline to Jamaica Plain

This is a super friendly ride from charming Brookline down to the heart of Jamaica Plain—perfect for a casual day out or a sunny commute. The route rolls over about 4 kilometers, mostly on smooth asphalt and well-maintained cycleways, so you can expect a comfortable, low-stress experience with not much traffic to worry about.

You'll leave behind Brookline's tree-lined streets and unique mix of historic homes and modern coffee shops, riding mostly on designated bike paths or quiet backstreets. Along the way, keep an eye out for leafy parks and some nice neighborhood views. The terrain is gentle, with only a mellow 28-meter ascent—barely enough to warm up your legs!

Your ride wraps up in Jamaica Plain, famous for its lively vibe, local eateries, and the nearby Arnold Arboretum—a great place for a stroll or a post-ride snack. With 90% of the journey on paved surfaces, this is an easy, enjoyable route for any cyclist looking to connect two of Boston’s coolest neighborhoods.