Quick ride by bicycle from South Boston to Boston

Kick off your ride in lively South Boston—known as “Southie” by locals—where you’ll pass classic triple-decker homes and maybe catch glimpses of the waterfront. This approximately 6 km route takes you north into downtown Boston, mixing up modern cycleways and quieter neighborhood roads for both safety and scenery.

You’ll climb a bit (keep an eye out for some short but steep sections!) but it’s balanced with some fun descents as you roll closer to Boston’s heart. The route is mostly paved and has some great stretches dedicated to bikes, which makes for a pretty smooth journey.

Cruising into the city center, you’ll find yourself minutes from iconic spots like Boston Common and Faneuil Hall—perfect for stopping to stretch or grab a coffee. It’s a great mix of residential charm and city hustle, ideal for commuters or anyone wanting a fun urban ride with plenty to look at along the way.