Quick ride by bicycle from Brookline to South Boston

Get ready for a fun ride! This cycling route starts in Brookline—a leafy suburb known for its historic neighborhoods and cozy cafes—and heads straight east to South Boston, a lively waterfront district famous for its Irish roots, harbor views, and packed summer beaches. You’ll cruise for about 11 kilometers, most of it on smooth paved surfaces, with over 70% of your ride on designated cycleways. Expect a gentle, rolling ride with minimal climbs (just over 70 meters of ascent), making it perfect for beginners or a chill spin after work.

Along the way, you’ll zip through some of Boston’s quieter neighborhoods, avoiding most busy streets. The scenery shifts from lovely residential vibes in Brookline to the urban energy of Southie, ending near the water. Don’t forget to grab a coffee when you get to South Boston—or better yet, reward yourself with a walk along Castle Island. Have a great ride!