

Route template
Brookline to Boston
Kick off your ride in leafy Brookline, known for its beautiful residential streets, historic homes, and cozy village vibe (did you know JFK was born here?). You’ll enjoy mostly smooth sailing—the majority of your 13-kilometer journey into Boston is on well-paved cycleways and quiet roads, perfect for a relaxed pace. As you head east, you’ll gently climb some small hills before cruising down toward the city, with the skyline growing ever closer.
Much of the route is on pleasant, designated bike paths, sending you past classic brownstones, riverside parks, and maybe the occasional café worth a stop. The closer you get to downtown Boston, the buzz grows—expect a bit more traffic but also the exciting energy of entering one of America’s historic urban centers, packed with museums, markets, and harbor views. You’ll roll into Boston feeling the pulse of the city and ready to explore, all fueled by a smooth ride from Brookline!
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The best bike routes from Brookline to Boston
Bike route to work
Cycling route in Brookline, Massachusetts, United States
- 6.1 km
- Distance
- 58 m
- Ascent
- 104 m
- Descent
Ruggles to Volpe
Cycling route in Brookline, Massachusetts, United States
- 5.1 km
- Distance
- 55 m
- Ascent
- 51 m
- Descent
vandy to barbershop deluxe
Cycling route in Brookline, Massachusetts, United States
- 3.7 km
- Distance
- 38 m
- Ascent
- 30 m
- Descent
ride through Boston
Cycling route in Brookline, Massachusetts, United States
- 11.5 km
- Distance
- 0 m
- Ascent
- 0 m
- Descent
Esplanade
Cycling route in Brookline, Massachusetts, United States
- 5.9 km
- Distance
- 30 m
- Ascent
- 67 m
- Descent
home -> coolidge corner
Cycling route in Brookline, Massachusetts, United States
- 4 km
- Distance
- 30 m
- Ascent
- 41 m
- Descent
Commuter Rail Ruggles
Cycling route in Brookline, Massachusetts, United States
- 4.5 km
- Distance
- 53 m
- Ascent
- 53 m
- Descent
bike shop
Cycling route in Brookline, Massachusetts, United States
- 4.7 km
- Distance
- 31 m
- Ascent
- 35 m
- Descent
Angel's route home
Cycling route in Brookline, Massachusetts, United States
- 6.6 km
- Distance
- 65 m
- Ascent
- 62 m
- Descent
Wellington Terr, Brookline to State St, Boston
Cycling route in Brookline, Massachusetts, United States
- 9.2 km
- Distance
- 25 m
- Ascent
- 32 m
- Descent
Recovered Route
Cycling route in Brookline, Massachusetts, United States
- 4.5 km
- Distance
- 21 m
- Ascent
- 45 m
- Descent
549 Huntington Ave, Boston to Columbus Park, Boston
Cycling route in Brookline, Massachusetts, United States
- 6 km
- Distance
- 38 m
- Ascent
- 48 m
- Descent
Discover more routes
- Esplanade
- Distance
- 5.9 km
- Ascent
- 30 m
- Descent
- 67 m
- Location
- Brookline, Massachusetts, United States
- home -> coolidge corner
- Distance
- 4 km
- Ascent
- 30 m
- Descent
- 41 m
- Location
- Brookline, Massachusetts, United States
- Commuter Rail Ruggles
- Distance
- 4.5 km
- Ascent
- 53 m
- Descent
- 53 m
- Location
- Brookline, Massachusetts, United States
- bike shop
- Distance
- 4.7 km
- Ascent
- 31 m
- Descent
- 35 m
- Location
- Brookline, Massachusetts, United States
- Angel's route home
- Distance
- 6.6 km
- Ascent
- 65 m
- Descent
- 62 m
- Location
- Brookline, Massachusetts, United States
- Wellington Terr, Brookline to State St, Boston
- Distance
- 9.2 km
- Ascent
- 25 m
- Descent
- 32 m
- Location
- Brookline, Massachusetts, United States
- Recovered Route
- Distance
- 4.5 km
- Ascent
- 21 m
- Descent
- 45 m
- Location
- Brookline, Massachusetts, United States
- 549 Huntington Ave, Boston to Columbus Park, Boston
- Distance
- 6 km
- Ascent
- 38 m
- Descent
- 48 m
- Location
- Brookline, Massachusetts, United States
Routes from Brookline
Quick ride by bicycle from
Brookline to South Boston
Quick ride by bicycle from
Brookline to Cambridge
Routes to Boston
Cycling day trip from
Needham to Boston
Quick ride by bicycle from
Cambridge to Boston
Quick ride by bicycle from
South Boston to Boston