By bicycle from Boston to Jamaica Plain

Ready for a city-to-suburb adventure? This ride starts right in the heart of Boston, a city steeped in Revolutionary War history and famous for its bustling streets and historic neighborhoods. You’ll cruise out of downtown, following mostly smooth asphalt paths—over 70% of your ride is on dedicated cycleways and quiet roads, making this a friendly route for all skill levels.

As you roll southwest, soak in glimpses of Boston’s iconic brownstones and maybe even swing past the Greenway. There’s a gentle mix of ups and downs, but nothing too strenuous—your total ascent is around 58 meters before dropping into leafy Jamaica Plain. Once there, you’ll find yourself in one of Boston’s loveliest, most diverse neighborhoods, home to the scenic Arnold Arboretum and the vibrant vibes of Centre Street.

All told, this nearly 10 km ride takes you from city buzz to tree-lined tranquility—perfect for a leisurely evening spin or a weekend jaunt!