For those of you who are new in the area, the Boston coast may seem a little confusing and even intimidating in a sense, as it is basically a huge C-shaped port with many angles and also appearing to have buildings and other development by blocking much of it. Because of this, it may seem that walking along the harbor for long stretches would be difficult if not impossible, but this is as far from reality as possible, since the city actually has a walkway called Harborwalk that basically runs from the Quincy Line to south to the Mystic River in Charlestown to the north. The path has some missing pieces here and there, while other parts of it are parallel and / or traversing busy roads, so if you like long walks, the key is to find a stretch of Harborwalk that does not break even though you have as few intersections roads possible. One section that does just that is the part between the JFK Library and the Museum / UMass in Boston at Dorchester and Castle Island at the south end of Boston, and you can get at least seven miles from this walk, almost anything that it is along the shore – while it can also be extended a few miles longer if you want a really long walk. Oh, and the middle point has a stop that will satisfy your hunger or will force you to Uber again at the start so you can take a nap (and more on this in a bit).
The JFK / UMass walk to Castle Island is actually one that brings the Appalachian Mountain Club (and I'm one of their leaders, anyway), so this is a well-established hike with a specific route. Ironically, it begins in a decidedly unattractive place: the JFK / UMass T station, which is located east of where the Southeast Expressway meets the Columbia Road, and the short walk from the subway station south along Morrissey Boulevard up adjacent Star Market may have you wondering what you hunted for. Now why, please, the route goes directly to the Star Market? Well, bathrooms, for example, since there are not many options for a few miles, plus if you need a snack, you can definitely have one here.
Whether you go to the supermarket or not, take the walkway that crosses Morrissey Boulevard and head north, keeping the subway station within sight on your left until you reach Mount Vernon Street, where you will turn a sharp right turn. Mount Vernon is not much to see, but you'll notice that things get quieter and you can feel that the ocean is not too far. A little over half a mile, you'll see that the apartment complex on the left ends and soon after the end is a path; take this and you will almost immediately be rewarded with spectacular views of the water, especially when the path meets with the Harborwalk, which goes in both directions.
Taking a right on the Harborwalk will take you to the JFK Library and Museum and to the UMass Boston, but unfortunately, the catwalk runs the busy Morrissey Boulevard for quite a while afterwards, even if you're trying to take a shorter walk, this is not bad, at least until Morrissey. Our excursion continues to the left, embracing the harbor as it winds through the Harbor Point / Columbia Point section of Dorchester with breathtaking views of the Boston Harbor Islands in one direction and the Boston Skyline in the other. This is a section of the city that is rarely explored, and the extraordinary views of the water really make it feel like a real discovery, so this is obviously a good place to take a break (or two) and immerse yourself completely.
ISYou will emerge from Harbor Point / Columbia Point to Carson Beach, a crescent-shaped strip of sand that marks the boundary between Dorchester and South Boston, and you can walk along a long walkway or jump to the edge of the water on the beach. , both are good options. Curving west then north then eastward, the Harborwalk and the beach walk merge when you start walking along Day Boulevard to Southie, and while this road may be busy, it's a walk very pleasant in part because this is the "old" "South Boston, with many well-maintained multi-family houses lining the tree-lined street and hardly any new development to find. (This part of the neighborhood is completely different from the hectic and hectic Seaport neighborhood a miles north, which is actually part of Southie although many residents would rather not consider it to be so.)
The stretch of the walk along Day Boulevard is very easy to follow as you keep the water on your right (as you have done since you left the Mount Vernon Street trail in Dorchester) and follow Day Boulevard to to the left, looking at the crossroads mostly passes through the alphabet that starts with G and eventually gets to P, with each block leading you to what appears to be farther and farther away to the sea. There are small walkways "spur" here and there on this stretch where you can lean against a wall or sit on a bench and admire the ever more breathtaking water views, and a bit later P Street and Farragut Road , you will see a shaded park on the left and a causeway to the right that goes directly to the ocean.
This causeway forms a circle with Pleasure Bay to the left and the Atlantic to the right and is called "Sugar Bowl" by locals, and is easily one of the most scenic parts of Boston – and one of the windiest, so clinging your hat if you have one. Head up the causeway and reach a pavilion-like area with a circle of benches, stopping for a view in all directions, then continue along the causeway while jogging and ending at Castle Island, a historic area that includes Fort Independence and has been used as a military fortification site since 1600.
Entering this strip of land, you can go left or right; while you can go either way, going to the right is a little more interesting, as it takes you along the perimeter of the fort and gives you views of the ocean and islands to the right and finally parts of the Skyline of Boston as it turns left around the fort. A fishing pier is located just before going left, and it is worth taking this brief detour on the right if you want to take a bench in the middle of the ocean and enjoy more views. The left turn of the catwalk takes you away from the water for a short time, and also makes a detour to Sullivan's, a legendary snack bar of choice from the locals offering the aforementioned hot dogs and burgers with fried clams , lobster rolls, chicken and fish sandwich, ice cream and more. Get something to eat if you're hungry, and then either sit in front or go up the hill to the fort if you want to get away from the crowd.
From Sullivan, keep walking counterclockwise along the Sugar Bowl, with the beginning (or the end) of Day Boulevard to your right now, and you'll soon meet the entrance to the causeway again. From here, you can simply head back along the Harborwalk, skip the Harbor Point / Columbia Point section and take Day Boulevard to the subway station, or if you want a few more miles (and more of those great views), head back towards Harbor Point / Columbia Point and then back to Mount Vernon Street. If you do the first, the whole path is between seven and eight miles; by doing this you will approach nine miles and, depending on your pace, plan to walk for about four hours.
Well, there you have it: a long walk to the beach that you can do without leaving the city, and one that is much more familiar to long-time residents and Bostonians than to newcomers. If you want to do a walk / lunch combination that takes you away from the crowd, but it's also very easy to get to, this is very hard to beat.
[The JFK/UMass T station is located on the Red Line, three stops from South Station going outbound toward Braintree/Ashmont.]