Quick ride by bicycle from Boston to South Boston

Ready for a city spin? This route lets you soak in both the buzz of downtown Boston and the laid-back vibes of South Boston—just under 5 km, so it’s a perfect ride whether you’re commuting or exploring.

Starting in the heart of Boston, you’ll roll through historic streets and iconic sights. Expect a mix of dedicated cycleways (almost half the route!), some quiet city roads, and just a brief dash on busier stretches. The surface is mostly paved or asphalt, making it a pretty smooth ride.

You’ll cruise southward, catching glimpses of old brick buildings, leafy parks, and maybe even a view of the harbor as you near “Southie.” South Boston is known for its waterfront, Irish heritage, and trendy cafes—plenty of spots to pause and grab a coffee at the end.

There’s a gentle climb early on, but you’ll end with a nice downhill stretch. It’s an easy, scenic route perfect for a weekday ride or a weekend jaunt to explore two of the city’s best neighborhoods!