Time - 23:45 minutes one way / no stopping
Average Speed: 12.08 mph
Skill level: Wicked easy
This bike ride begins at Castle Island, breezes along the waterfront and beaches of South Boston and finishes at the entrance to Umass in Dorchester. The sidewalks are double wide most of the way, so riding close to the water and enjoying the view is an option. On really nice weekends there might be some congestion from walkers, joggers, dogs and extended families with their brood running amuck. When I cycled this route on a mid-week afternoon the only thing I really had to battle was a blustery wind.
Several years ago this length of waterfront did not have a continuous track from end to end. It’s now part of the extended Harborwalk, which has a cleared path around Columbia Point’s housing and the Umass Campus. Once you get past the beaches and some of the craziness that is Southie, it’s quite a peaceful ride - with some tucked away green spaces and unique views of the city skyline. This really is the only decent shoreline bike ride in Boston proper - the Waterfront area along downtown and Fan Pier is just not suited for biking.
Give yourself about an hour and a half for the complete ride if you plan on taking some photos, bringing the kids or exploring a little. Sometimes I like to stroll parts of the coastline during low tide to see what kind of crazy crap comes drifting ashore. There’s a peaceful little oasis right behind the JFK Library with some picnic tables, lush grass and lots of shade trees. The area past the Umass entrance can be explored, where the Harborwalk officially ends, over to the Savin Hill / Malibu Beach area, but the route breaks up and traffic along Morrissey Blvd can be a pain in the ass.
The shady oasis behind the JFK Library
As you finish up your trip back on Castle Island, don’t forget to reward yourself at Sullivan’s. This take-out bayside shanty servers burgers, dogs and food from the sea, and is a place of pilgrimage for the locals. I guess there’s something special about chowing down on a lobster roll while gazing out at that dead crustacean’s recent home. You can’t beat the prices though – I bought a hot dog and fries for $3.80. There aren't any glamorous attractions along this waterfront though; no boardwalk with games, rides or fried dough…thankfully. If you’d like something a little more upscale than Sullivan’s, or maybe an adult beverage, try Local 149 at the corner of E. 6th and P St. They’ve got a great beer list, and you know a pub is serious about their charcuterie when they plop a giant meat slicer right on the bar (this is the post Whitey Bulger era of Southie - no doubt). And feel free to enjoy the beautiful beaches of Boston, I wouldn’t necessarily swim here...but there are plenty of people who dive right in!