How cycling in Brookline could look like.
How cycling in South Boston could look like.

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

38 min
Duration
11 km
Distance
72 m
Ascent
72 m
Descent
17.4 km/h
Avg. speed
32 m
Max. altitude

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!

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From our community

The best bike routes from Brookline to South Boston

578 Huntington Ave, Boston to 141 Dorchester Ave, Boston
City bike
0

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
0

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
Recovered Route
Road bike
Harrison Ferguson
0

Recovered Route

Cycling route in Brookline, Massachusetts, United States of America

62 km
Distance
582 m
Ascent
640 m
Descent
0

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
bar crawl
City bikePaved
0

bar crawl

Cycling route in Brookline, Massachusetts, United States of America

vfvfvfvffvf
10.8 km
Distance
57 m
Ascent
87 m
Descent
0

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
0

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
0

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
0

7 Speare Pl, Boston to 389 W Broadway, Boston

Cycling route in Brookline, Massachusetts, United States of America

4.8 km
Distance
20 m
Ascent
13 m
Descent
0

23 Forsyth St, Boston to 389 W Broadway, Boston

Cycling route in Brookline, Massachusetts, United States of America

4.7 km
Distance
20 m
Ascent
13 m
Descent
0

912 Beacon St, Boston to 524 Massachusetts Ave, Boston

Cycling route in Brookline, Massachusetts, United States of America

3.2 km
Distance
20 m
Ascent
21 m
Descent
0

amanda

Cycling route in Brookline, Massachusetts, United States of America

8.8 km
Distance
93 m
Ascent
95 m
Descent

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