For those of you who are new to the area, the Boston coastline may seem a bit confusing and even intimidating in some ways, as it is basically a huge C-shaped harbor with many nooks and crannies while also appearing to have buildings and other development blocking much of it. Because of this, it might seem like walking along the harbor for long stretches would be difficult if not impossible, but this is as far from the truth as you can get, as the city actually has a walkway called the Harborwalk that basically goes from the Quincy line to the south all the way up to the Mystic River in Charlestown to the north. The path does have some pieces missing here and there, while other parts of it parallel and/or cross busy roadways, so if you like long walks, the key is to find a stretch of the Harborwalk that isn’t broken up while also having as few road crossings as possible. One section that does just that is the part between the JFK Library and Museum/UMass Boston area in Dorchester and Castle Island at the very tip of South Boston, and you can get at least seven miles out of this walk—nearly all of which is along the shore—while it can also be extended a few more miles if you want a really long walk. Oh, and the midway point has a stop that will either satisfy your hunger or force you to Uber it back to the start so you can nap (and more on this in a bit).
The JFK/UMass to Castle Island walk is actually one that the Appalachian Mountain Club leads (and I am one of their leaders, by the way), so this is an established hike with a specific route taken. Ironically, it starts at a decidedly unattractive place—the JFK/UMass T station, which is just east of where the Southeast Expressway and Columbia Road meet, and the brief walk from the subway station south along Morrissey Boulevard to the adjacent Star Market may have you wondering what you’ve gotten yourself into. Now why, pray tell, does the route go to Star Market right off the bat? Well, bathrooms, for one, since there aren’t many options for a few miles, plus if you need a snack, you can certainly get one here.
Whether you go to the grocery store or not, take the walkway that goes over Morrissey Boulevard and head back north, keeping the subway station within sight to your left until you reach Mount Vernon Street where you will take a sharp right. Mount Vernon isn’t much to look at, but you’ll notice that things quickly get quieter and you may sense that the ocean isn’t too far away. A bit more than a half mile in, you’ll see that the apartment complex to the left ends and right after the end is a pathway; take this and you’ll almost immediately be rewarded with spectacular water views, especially as the trail meets up with the Harborwalk, which goes in both directions.
Taking a right on the Harborwalk will take you to the JFK Library and Museum and UMass Boston, but unfortunately, the walkway goes along the very busy Morrissey Boulevard for quite a stretch after that, though if you’re looking to do a shorter walk, this isn’t a bad one, at least up to Morrissey. Our hike goes left, hugging the harbor as it winds its way through the Harbor Point/Columbia Point section of Dorchester with jaw-dropping views of the Boston Harbor Islands in one direction and the Boston Skyline in the other. This is a section of the city that rarely gets explored, and the extraordinary water views really make it feel like a true find, so this is obviously a good place to take a break (or two) and soak it all in.
Eventually, you’ll emerge from Harbor Point/Columbia Point at Carson Beach, a crescent-shaped strip of sand that marks the border between Dorchester and South Boston, and you can either walk along a long boardwalk or hop right down to the water’s edge on the beach, both of which are good options. Curving west then north then east, the Harborwalk and the beach walk merge back together as you start to walk along Day Boulevard in Southie, and while this road can be a bit busy, it’s a very pleasant walk in part because this is the “old” South Boston, with lots of well-maintained multifamily homes lining the tree-shaded street and almost no new development to be found. (This part of the neighborhood is completely different from the bustling and hectic Seaport District a mile to the north, which is indeed part of Southie though many residents would rather not consider that to be the case.)
The stretch of the walk along Day Boulevard is very simple to follow, as you keep the water to your right (as you’ve been doing ever since emerging from the Mount Vernon Street pathway in Dorchester a while back) and follow Day Boulevard to the left, watching the cross streets mostly go through the alphabet starting with G and eventually getting to P, with each block taking you what seems to be further and further out to sea. There are little “spur” walkways here and there on this stretch where you can lean against a wall or sit on a bench and take in the increasingly breathtaking water views, and a bit after P Street and Farragut Road, you’ll see a shaded park on the left and a causeway on the right that heads directly out to the ocean.
This causeway forms a circle with Pleasure Bay on the left and the Atlantic on the right and is called the “Sugar Bowl” by locals, and it is easily one of the most scenic parts of Boston—and one of the windiest, so hold onto your hat if you have one. Head onto the causeway and walk out to a pavilion-like area with a circle of benches, stopping for views in all directions, then continue along the causeway as it jogs left and ends up at Castle Island, an historic area that includes Fort Independence and has been used as a military fortification site since the 1600s.
Upon entering this strip of land, you can either go left or right; while you can go either way, going right is a bit more interesting, as it takes you along the perimeter of the fort and gives you views of the ocean and the islands to the right and eventually parts of the Boston Skyline again as you turn left around the fort. A fishing pier can be found just before heading left, and it’s worth taking this very short detour to the right if you want to grab a bench out in the middle of the ocean and soak up more views. The left turn of the walkway takes you away from the water for a short time, and it also makes a beeline toward Sullivan’s, a legendary snack shack favored by locals that offers the aforementioned hot dogs and burgers along with fried clams, lobster rolls, chicken and fish sandwiches, ice cream, and more. Grab some food if you’re hungry, and then either sit out front or head up the hill toward the fort if you want to get away from the crowds.
From Sullivan’s, keep walking counterclockwise along the Sugar Bowl, with the start (or end) of Day Boulevard to your right now, and soon you’ll meet up with the causeway entrance once again. From here, you can simply walk back along the Harborwalk, skipping the Harbor Point/Columbia Point section and taking Day Boulevard right back to the subway station, or if you want some extra miles (and more of those great views), head back toward Harbor Point/Columbia Point and then back to Mount Vernon Street. If you do the former, the entire route is between seven and eight miles; doing the latter will get you closer to nine miles, and depending on your pace, expect to be out walking for about four hours or so.
Well, there you have it: a long seaside walk that you can do without leaving the city, and one that’s really more known to locals and longtime Bostonians than newcomers. If you want to do a combination walk/lunch that takes you far away from the crowds while also being very easy to get to, this is one that is very tough to beat.
[The JFK/UMass T station is located on the Red Line, three stops from South Station going outbound toward Braintree/Ashmont.]