Eat like a sea captain

The Square Rigger’s classic coastal cuisine.


We sat around a circular mahogany table by the window in the corner of the back room. There are two main dining spaces inside the Square Rigger Restaurant in Edgartown. The first is in the front by the entrance and bar; the second wraps around back. There’s an old fireplace set against a back wall; it’s adorned with original, nautical, authentic aesthetic. Lights are dim, and soft conversation fills the space. The takeout window may be closed, but the Square Rigger Restaurant offers a year-round bite of summertime.

I’ve heard from longtime locals that the Square Rigger was once “the spot.” It’s where friends would gather and drink, and stay until well after midnight. Nowadays, it closes around 9, but people are still gathering and still drinking; there’s just a lot more eating going on.

I opened up the menu and saw seafood, steaks, filets, pastas, and more seafood. It’s a fish-filled menu, but that makes a lot of sense. The Square Rigger is a circa 1800s sea captain’s house, and its menu might as well reflect that.

Before committing to any dinner items, we looked at the drink menu. There was an extensive list of martinis and cocktails, some with names I’d never heard before. Being a creature of habit, and hoping for an extra kick of energy on this Friday night after a long week, I ordered an Espresso Martini. My friend went with the Moscow Mule, and my boyfriend went for a Sierra Nevada.

After our drinks came out, our server brought over a golden-brown whole loaf of lightly toasted bread. Bread before meals has turned into a rare occurrence for me when I go out to dinner, so this was noted and especially appreciated.

I started off with a cup of Clam Chowder ($7). It was served in a mini glazed bowl with a dusting of paprika on top, then I loaded it up with pepper. It’s filled with bits of fresh clam, potatoes, onions, and celery. No cup of clam chowder is complete without the crunch of oyster crackers, so I poured a pack of those in.

All of Square Rigger’s entrées come with a side salad, which is another rarity among my recent restaurant experiences. You can choose from a long list of dressing options — we went balsamic vinaigrette and Parmesan peppercorn.

Square Rigger’s timing and service was spot-on. Shortly after we finished bread, apps, and salads, our entrées came out. We ordered Fish and Chips, a Lobster Roll, and Sea Scallops. The Fish and Chips were lightly fried fillets of a white, flaky, light, native fish. It was served with a heaping pile of salty golden french fries, cut thin and crispy, with a side of coleslaw.

The Lobster Roll was served with large chunks of local lobster meat and drizzled with herbed lemon butter. It was served hot and salty with a side of french fries. The Scallops were carmelized with butter, lemon, and paprika. They tasted simple, light in texture, and were cooked fresh. The vegetable of the day was a warm butternut squash — served sweet and buttery, and didn’t distract.

We forwent dessert in the name of being extremely full. Square Rigger dishes average around $25, but they come with plenty of food — more than usual, if you ask me. They’ll be open through Jan. 1, Thursday through Saturday, from 5 to 9 pm. Dodge the cold, drop in while you can, and eat like a sea captain.


The Square Rigger Restaurant is located at 225 Edgartown–Vineyard Haven Road in Edgartown, right in the Triangle. For more information, call 508-627-9968, or visit the website,