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Pizza and more at Short & Main in Gloucester
Pizza and more at Short & Main in Gloucester
Ren Fuller

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Eat and Drink Your Way Through Downtown Gloucester

Some raw bar here, a freshly brewed lager there

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.


One way to spend a spring or summer weekend away from Boston: Take a trip up Routes 128 and 133 to Cape Ann, specifically to Gloucester. The most industrial of the Cape Ann locales, Gloucester isn’t without its share of breathtaking vistas. (It is situated on the Great Marsh, after all.)

When hanging in Gloucester, one should make a point to dip a toe or two at Good Harbor and Wingaersheek beaches, and one should ride — whether by car or bicycle — down Route 127 through the adorable hamlets of Lanesville and Annisquam. However, this particular crawl is all about eating and drinking downtown.

Gloucester is full of excellent watering holes and restaurants, and this is by no means an exhaustive list but rather a suggestion of stops for a single day trip. By all means, head back to “the place to be in the summer” as much as you can — especially for St. Peter’s Fiesta, which will take place between June 26 and 30 this year.


Pizza at Short & Main

36 Main St., Gloucester

short and main
Get wood-fired pizza and more at Short & Main

Two of Short & Main’s owners met while cooking at Chez Panisse, Alice Waters’ famed Berkeley, California, restaurant, and it shows — the food is the truth (as is the wine). Start with some pizza, which is cooked in a wood-fired oven. The menu changes frequently, but if it features the Ricardo, get the Ricardo — it’s topped with tomatoes, sopresatta, scamorza, red onion, hot peppers, oregano, and pickled hot peppers.

Raw Bar and Cocktails at Minglewood Harborside

25 Rogers St., Gloucester

Minglewood in Gloucester
Minglewood in Gloucester

As the name would suggest, Minglewood Harborside is situated adjacent to the Gloucester harbor. There’s patio seating with a water view, and you should sit there while slurping back oysters and cocktails.

A Freshly Brewed Lager or Two at Cape Ann Brewing Co.

11 Rogers St., Gloucester

The Pub at Cape Ann Brewing Co.
The Pub at Cape Ann Brewing Co.

The Pub at Cape Ann Brewing Co. is situated at the foot of downtown Gloucester. Stop in for a very fresh pint (or two, or three, as long as you’re walking or have a designated driver) of Fisherman’s Brew. It’s the brewery’s best offering, and it’s criminally underrated.

As Much As You Can Handle at Passports

110 Main St., Gloucester

passports gloucester
Passports is a Gloucester classic

Passports is a Main Street mainstay. Its menu is sort of all over the map — which is apt — but in the good way. There’s Thai influence, there’s New England influence, there’s French influence, there are salads, there are sandwiches, there are vegetarian options, there are things from the land, there are things from the sea...you get the point. Best advice: Order something from the specials menu. It won’t disappoint. Nothing at Passports ever does.

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