By bicycle from Boston to Brookline

Set out from the heart of Boston and roll your way to the charming town of Brookline on a relaxed 10.5 km ride. Leaving behind Boston’s historic streets—think old brick buildings and iconic parks—you’ll cruise along mostly dedicated cycleways and some quiet roads, making for a largely stress-free spin. The route is mostly smooth asphalt, with a few short sections where the surface changes but nothing your tires can’t handle.

You'll pass through bits of leafy neighborhoods and local hotspots, gradually moving from Boston’s lively downtown vibe to Brookline’s calmer, tree-lined streets. Brookline itself is known for its village feel and vibrant food scene—so plan a café stop if you’ve got time! Total climbs are mild, with a gentle ascent and slightly more downhill, topping out at just over 41 meters above sea level. Perfect for a casual roll, a weekend outing, or a scenic commute between two of Greater Boston’s most characterful spots.