An Afternoon in Boston

For our afternoon in Boston, we will start off in a little-known alley in the Financial District, Winthrop Lane. When walking through this small pedestrian alley between Arch and Otis streets, make sure to look down. Embedded in the brickwork are bronze encrusted bricks which showcase Boston’s history as well as its present. There are about 100 of these such bricks which commemorate historical events such as the Boston Tea Party, stuff that is purely Boston such as the Boston Marathon, and funny Boston-isms such as a Muppet-esque angry driver. 

It’s a quick diversion but one that I was curious about since I am quite familiar with the city. It’s fun to spot all of the bricks and also to look like a weirdo, taking pictures of curiosities that most passersby simply use as a pedestrian path.

Castle Island

Our next destination for our afternoon in Boston is Castle Island in South Boston. Any local will undoubtedly know that Castle Island is not actually an island, but presumably, most outsiders would venture to guess that Castle Island would require a boat of some sort (or maybe a long bridge) to set foot on. Massachusetts does this to outsiders, for instance dropping route signs in the middle of an intersection to let the driver guess as to whether they are still on the correct road. 

In actuality, Castle Island is a 22-acre state park best known as the location for Fort Independence. It’s also the location of the snackbar mainstay, Sullivan’s. Even though Sullivan’s has been grilling up grub on Castle Island since 1951, this does not compare with the longevity of the fort. The current stone structure was built in 1851, but this location has been fortified since 1634, making it the oldest such place in America that has been in continuous use as a fort. Although the fort is not used for defense today, it has become a tourist attraction in its own right. The fort never actually saw military action, but it did inspire a former soldier. Edgar Allan Poe was stationed at the fort and was inspired by a legend about a lieutenant, Robert F. Massie, who was killed in a duel after an argument. The legend relates that Massie’s friends coaxed the killer, Gustavus Drane, into a state of inebriation and then suffocated him by walling him up into a vault in the fort, thus inspiring the Poe classic The Cask of the Amontillado. 

Castle Island is a popular recreation area for Boston residents and visitors alike. There is a beach for swimming, a playground, many routes for walking, and parkland for picnicking. The most popular route is the walkway around the perimeter of the fort. (My kids were more enamored with the playground than the fort, ironically.)

Sullivan’s

The best (and only) place to eat at Castle Island is Sullivan’s. Sullivan’s is somewhere between a takeout stand and a restaurant. Customers line up inside the brick facade to order their meals. There is no waitstaff or tables inside. Instead, it is grab and go. In addition to your car, there are plenty of other seating options. Just outside of Sullivan’s is a collection of picnic tables plus an ample amount of seating on benches, beachside, or on the grass. 

The food in Sullivan’s is not fancy but it sure is good. The adage they swear by is “quality food at reasonable prices.” This slogan is as relevant today as it was sixty years ago. Sullivan’s is most famous for its hot dogs. What makes their pork and beef steamed dogs so delicious beats me, but I swear they are truly fantastic. These snap when bitten into. I typically opt for a slew of toppings such as mustard, relish, and onions; sometimes I’ll make it a chili dog. The hot dog itself though, even plain, is so good. 

People also flock to Sullivan’s for its seafood selection. The variety of fried seafood includes clams–both whole bellies and strips, shrimp, and fish. Their lobster roll is a sight to behold. For dessert, it’s ice cream. Another Sullivan’s favorite is the raspberry lime rickey. This is a classic New England summertime-sipper. It’s simply seltzer, raspberry syrup, and lime. Truly refreshing. We opted for a double cheeseburger, a few hot dogs, and a lobster roll for our afternoon in Boston lunch. 

An Afternoon in Boston

Finding bricks emblazoned with Boston tidbits, running amuck at Castle Island, and eating a few hot dogs along the way sounds like a perfect way to spend an Afternoon in Boston!

For more afternoon adventures, check out Newton, New Jersey, and Stamford.