Welcome back to Food Crawls, a series in which Eater Boston staffers guide you (virtually) on various food (and booze) crawls in the Boston area.
When we go out, we often find ourselves wanting to try more than one restaurant or bar at a time — a drink and a snack here, another drink and perhaps a dessert there — and want to share our favorite multi-stop combinations with you. These crawls are meant to be relatively walkable, and the amount of food and drink is meant to correspond roughly to a couple of average appetites (so bring a friend), although your mileage may vary. Email us if there’s a particular theme, specific dish or drink, or neighborhood you’d like to see covered in a future installment.
Rockport sits at the tip on Cape Ann, and because it’s situated on the commuter rail, it makes for a perfect day trip for restless Bostonians looking to get out of the city to take in some extremely quaint New England.
Compulsory to any Rockport sojourn is a stroll up Bearskin Neck. The picturesque street is lined with boutiques and art galleries and eateries, and it ends in a jetty stretching out into Sandy Bay. Peer out at the cold void of the harsh Atlantic, and then make your way back toward Main Street.
Buy an abstract painting or some beach town kitsch, and then gorge on lobster rolls and ice cream (and several other treats).
Here’s where to go and what to eat on one food-filled jaunt through Rockport.
A Lobster Roll at Roy Moore’s Fish Shack
21 Dock Sq., Rockport
Roy Moore’s Fish Shack is never not busy. The Rockport institution does the standard New England fried seafood very well and also mixes it up with dishes like the fisherman’s reuben (sounds awful, but cheese on fish works in the case of fried haddock). The play here is the very simple lobster roll, however.
Bouillabaisse at Blue Lobster Grille
15 Dock Sq., Rockport
Yes, there’s bouillabaisse on Cape Ann. And it’s good. Blue Lobster Grille’s version is served with linguine, and it is decidedly more southern Italian than southern French, but that’s fine: It’s hard to care about authenticity when staring at a giant bowl filled with shrimp, scallops, haddock, calamari, lobster, and mussels.
A Dog at Top Dog
2 Doyle Cove Rd., Rockport
The hot dogs at Top Dog have names like Man’s Best Friend and German Shepherd. Top Dog can be forgiven for this because the hot dogs — yes, even the Italian Greyhound — are tempting. Try one topped simply with sauerkraut.
Something a Bit More Fancy at Feather & Wedge
5 Main St., Rockport
Feather & Wedge’s menu changes daily and finds influence from across the globe. A recent menu included cod served with tabouleh, harissa, and mizuna greens; pho served with braised pork; and Thai green curry. The walls are lined with images of Cape Ann granite quarry workers from the middle 19th century through the early 20th century. (The restaurant takes its name from a tool and process used to split pieces of granite). A full meal isn’t requisite — have a drink, slurp some oysters, and keep the food crawl going.
Austrian Sweets at Helmut’s Strudel
69 Bearskin Neck, Rockport
This Austrian pastry shop is in one of the most adorable buildings on Cape Ann. Its appearance is somewhere between slightly miniaturized Cape Cod-style home and converted boathouse, and its weathered cedar shingles are endemic to coastal New England. It’s fine to eat at Helmut’s during any weather, but it feels most appropriate to eat an apple strudel on a day that’s a bit cold and dank.
Ice Cream at the Ice Cream Store, Robins Nest, or Sundays
14 Bearskin Neck, 1 Main St., or 3 Bearskin Neck, Rockport, respectively
The Ice Cream Store has a Back Harbor view and is, like Helmut’s, adorable, and it serves American-style ice cream, while Robins Nest is the spot for gelato. It is possible to get a massive sundae at Sundays. It is also possible to get the right amount of ice cream, which is one scoop perched atop a sugar cone. Try the mint chocolate chip.
As far as these three ice cream shops go, where you go will be determined by your mood.