Sullivan's is the kind of place your grandfather might have taken your grandmother when they were dating — a place for cheap eats, a romantic stroll, and necking in the parking lot. Open since 1951, the Southie mainstay — offering hamburgers for less than $2 and some of the only crinkle-cut fries in Boston — is nestled in the corner of Castle Island, an old fortress turned mob haunt turned family park.
Sullivan's is charming in that peculiar Boston way that is somehow really unwelcoming while still making you feel right at home. On a nice day, the infamous line wraps all the way around the parking lot; tight-lipped townie cashiers brusquely take your order. Intimidating, maybe, but this no-frills system is efficient — you'll get your food in 10 minutes. During my visit, I was lucky enough to nab a picnic table (there's no inside seating).
Since their patties are pretty thin, Sullivan's only cooks them well-done, but my burger — with lettuce, tomato, mayo, and ketchup — still packed plenty of flavor. It's not gourmet, but for $1.90, I wasn't looking for anything fancy.
A large side of French fries ($1.95/small; $3.25/large) is pricier than anything else on the lunch menu, but totally worth it. Hot and delicious, these fries serve as a reminder of a better time, when crinkle-cut fries weren't so rare. The large is just enough to split between two people — or sate the cravings of a crinkle-cut junkie.
Sullivan's also has one of the best-priced lobster rolls around — for $9.95, you get a toasted hot-dog bun overflowing with quality lobster meat, lightly dressed in mayonnaise. Sullivan's doesn't screw around with celery or lettuce or distracting spices; they skip straight to the good stuff, letting the natural seafood flavor shine through.
After your meal, take a stroll around the island, play soccer in the grass, or lie on the beach — the greenery of the park against the harbor view proves that city-dwellers don't have to roam far for a quick escape from urban bustle. But anyone planning to make the trek on a rainy day, take heed: Sullivan's will close "if there are more seagulls than cars in the parking lot."
Sullivan's, located at 2080 Day Boulevard in South Boston, is open from the last weekend in February to the last weekend in November, seven days a week, 8:30 am–sunset, unless the weather is bad. Call 617.268.5685 or visit sullivanscastleisland.com.