

Quick ride by bicycle from Brookline to South Boston
Customize your own route based on our template or discover how our community prefers to cycle from Brookline to South Boston.
Route template
Brookline to South Boston
Hey there, cycling enthusiast! If you're looking for a laid-back ride, why not pedal from Brookline to South Boston? This 11-kilometer route is mostly on cycleways and quiet roads, making it a smooth journey on mostly asphalt and concrete surfaces.
You'll kick off in Brookline, a charming suburb known for its diverse architecture and vibrant town center. Be sure to take in the leafy streets and maybe grab a coffee at one of the local cafes before you set off.
Your ride will be a gentle roll, with about 72 meters of ascent and descent, peaking at just over 32 meters above sea level. The route is mostly flat, ensuring a leisurely ride that lets you focus more on the scenery than on thigh-busting climbs.
As you pedal closer to South Boston, say hello to the harbor views. Southie, as the locals call it, is famous for its strong Irish heritage and stunning waterfront. After this picturesque ride, you can treat yourself to some fresh seafood or take a stroll along the historic Castle Island.
Grab your helmet, hop on that bike, and enjoy the ride from the leafy suburbs to the breezy waterfront!
Community
Top users in this region
From our community
The best bike routes from Brookline to South Boston
578 Huntington Ave, Boston to 141 Dorchester Ave, Boston
Cycling route in Brookline, Massachusetts, United States of America
- 4.7 km
- Distance
- 56 m
- Ascent
- 51 m
- Descent
Recovered Route
Cycling route in Brookline, Massachusetts, United States of America
- 62 km
- Distance
- 582 m
- Ascent
- 640 m
- Descent
369 Huntington Ave, Boston to 380 W Broadway, Boston
Cycling route in Brookline, Massachusetts, United States of America
- 4.7 km
- Distance
- 53 m
- Ascent
- 44 m
- Descent
23 Forsyth St, Boston to 382 W Broadway, Boston
Cycling route in Brookline, Massachusetts, United States of America
- 4.8 km
- Distance
- 38 m
- Ascent
- 44 m
- Descent
210 Riverway, Boston to 72 E Concord St, Boston
Cycling route in Brookline, Massachusetts, United States of America
- 3.9 km
- Distance
- 8 m
- Ascent
- 11 m
- Descent
204 Hemenway St, Boston to 382 W Broadway, Boston
Cycling route in Brookline, Massachusetts, United States of America
- 4.7 km
- Distance
- 45 m
- Ascent
- 57 m
- Descent
369 Huntington Ave, Boston to 389 W Broadway, Boston
Cycling route in Brookline, Massachusetts, United States of America
- 4.9 km
- Distance
- 23 m
- Ascent
- 14 m
- Descent
bar crawl
Cycling route in Brookline, Massachusetts, United States of America
- 10.8 km
- Distance
- 57 m
- Ascent
- 87 m
- Descent
11–29 Forsyth St, Boston to 382 W Broadway, Boston
Cycling route in Brookline, Massachusetts, United States of America
- 4.8 km
- Distance
- 36 m
- Ascent
- 37 m
- Descent
32 Wensley St, Boston to 481–499 Athens St, Boston
Cycling route in Brookline, Massachusetts, United States of America
- 7.1 km
- Distance
- 53 m
- Ascent
- 64 m
- Descent
175 Hemenway St, Boston to 389 W Broadway, Boston
Cycling route in Brookline, Massachusetts, United States of America
- 4.7 km
- Distance
- 37 m
- Ascent
- 31 m
- Descent
541–575 Huntington Ave, Boston to 14 Allstate Rd, Boston
Cycling route in Brookline, Massachusetts, United States of America
- 7.8 km
- Distance
- 288 m
- Ascent
- 294 m
- Descent
Discover more routes
- 210 Riverway, Boston to 72 E Concord St, Boston
- Distance
- 3.9 km
- Ascent
- 8 m
- Descent
- 11 m
- Location
- Brookline, Massachusetts, United States of America
- 204 Hemenway St, Boston to 382 W Broadway, Boston
- Distance
- 4.7 km
- Ascent
- 45 m
- Descent
- 57 m
- Location
- Brookline, Massachusetts, United States of America
- 369 Huntington Ave, Boston to 389 W Broadway, Boston
- Distance
- 4.9 km
- Ascent
- 23 m
- Descent
- 14 m
- Location
- Brookline, Massachusetts, United States of America
- bar crawl
- Distance
- 10.8 km
- Ascent
- 57 m
- Descent
- 87 m
- Location
- Brookline, Massachusetts, United States of America
- 11–29 Forsyth St, Boston to 382 W Broadway, Boston
- Distance
- 4.8 km
- Ascent
- 36 m
- Descent
- 37 m
- Location
- Brookline, Massachusetts, United States of America
- 32 Wensley St, Boston to 481–499 Athens St, Boston
- Distance
- 7.1 km
- Ascent
- 53 m
- Descent
- 64 m
- Location
- Brookline, Massachusetts, United States of America
- 175 Hemenway St, Boston to 389 W Broadway, Boston
- Distance
- 4.7 km
- Ascent
- 37 m
- Descent
- 31 m
- Location
- Brookline, Massachusetts, United States of America
- 541–575 Huntington Ave, Boston to 14 Allstate Rd, Boston
- Distance
- 7.8 km
- Ascent
- 288 m
- Descent
- 294 m
- Location
- Brookline, Massachusetts, United States of America
Routes from Brookline
Quick ride by bicycle from
Brookline to Cambridge
Quick ride by bicycle from
Brookline to Boston
Routes to South Boston
Quick ride by bicycle from
Boston to South Boston