Down-home, classic southern food is what pulls locals through Tupelo's doors, and the rustic charm and hospitality are what keep them at the table—downing andouille-and-okra-flecked gumbo and plates of fried oysters. Oh, and those folks wandering in after 9 p.m. looking for crispy grits and locally produced brews? Ain't no thang; this is one joint where that kind of behavior is encouraged. 1193 Cambridge St., Cambridge, MA 2139, tupelo02139.com.
With a brewery, distillery, and winery all surrounding one chill courtyard, this is the perfect place to while away a few afternoon hours on the Grey Lady. Sip a Summer of Lager, slurp oysters (if you're lucky enough to catch the occasional raw bar), and play cornhole, all set to live tunes played by local musicians. Bonus: It's located off the new Hummock Pond Road bike path, so you can safely coast there and back to town. 5 Bartlett Farm Rd., Nantucket, MA ciscobrewers.com.
Bellying up to the bar has never felt so sophisticated as it does at Chez Henri, a classic Cambridge bistro. The bar fare—like that offered in the dining room—strikes a balance between French and Cuban cuisines: grilled homemade chorizo, duck tamales, oysters with Muscat mignonette, guava barbecue fritters, and artisanal cheeses. Wash down the global grub with something from the equally worldly wine list, which offers selections ranging from Alsace to Argentina. We like it here so much that we'll even forgive them for serving Derek Jeter when he stopped in for a bite last spring. One Shepard St., Cambridge, MA 2138, chezhenri.com.
We're tempted to call what Redd's does "home cooking," but given that this version of comfort food would require an apprenticeship at a southern barbecue joint, the ability to break down an entire pig, and a smoker in the backyard, we're not exactly talking about our home. Redd's nails everything, from the house-made pickle plate (try the pickled cabernet grapes) and apple mignonette-topped raw oysters to the just-about melt-in-your-mouth pulled-pork sandwich. If this is how you cook at home, we're coming over for dinner. 4257 Washington St., Roslindale, MA 2131, reddsinrozzie.com.
Within weeks of its spring opening, this spot from Ten Tables maven Krista Kranyak won the hearts of J.P. residents with Parmesan-truffle fries, Baileys-spiked vanilla milkshakes, and (what else?) grass-fed burgers topped with everything from harissa aioli to fried oysters. There are lots of other great options, too, like fried-shrimp po' boys, turkey clubs, and kraut-topped hot dogs. Little surprise, then, that the small space is packed nightly with stroller-toting families eating elbow-to-elbow with too-cool hipsters. 605 Centre St., Jamaica Plain, MA 2130, grassfedjp.com.
Red wine with meat, white wine with fish—whoa, not so fast! Wine director Sandy Block has compiled 40 pages (because 41 would just be silly) of bottles selected in blind tastings for menu compatibility, resulting in the ideal muscadet for those oysters and the right sangiovese for that spicy cioppino. Some three dozen vintages are available by the glass, and there are five tasting flights (three priced under $10) that change from one visit to the next. The inventory at last year's ace, Troquet, is still worthy, but at the end of the day the options and value are at Legal. 26 Park Plaza, Boston, MA 2116, legalseafoods.com.
The low-key town of Duxbury is better known for bivalves than brioche, but that doesn't keep this café's Paris-born bakers (the same artistes behind Café Vanille in Boston and Chestnut Hill) from turning out the most decadent pastries on the South Shore. Flaky napoleons, rich éclairs, petite financiers, elegant pear tarts, all types of crusty loaves, and other French classics beckon from the shelves, but it's the enormous croissants—especially apricot and chocolate—and the chewy-moist coconut macaroons (a.k.a. congolais) that really convince pastry lovers that the world's their oyster. 459 Washington St., Duxbury, MA 2332, frenchmemories.com.
Before you board the ferry in Oak Bluffs, make time for one more taste of island living at its greasy, salty, satisfying best: a cardboard box full of Giordano's fried clams. Housed in a no-frills walk-up stand (there are a couple of picnic tables outside) just across from the Flying Horses carousel, Giordano's fries the clams in a light batter until they're crisp and serves them with fresh tartar sauce and lemon wedges. You could order a side of crunchy, boardwalk-style fries, but leave room instead to sample the superlative fried oysters or a lobster roll. 107-109 Circuit Ave., Oak Bluffs, MA giosmv.com/.
The recent shuttering of seafood landmark Island Creek Oyster Bar has made us even more protective of chef Jeremy Sewall’s legendary lobster roll, which lives on (thank heavens!) at his Row 34. There we find heaping portions of sweet and tender meat, caught by Sewall’s cousin, a Maine lobsterman. It’s served tossed in warm butter and sprinkled with sea salt, or mixed with cool mayo, cr&_egrave;me fra&_icirc;che, and pickles for “Ethel’s Lobster Roll,” named for Sewall’s grandmother — a family recipe for lasting success if there ever was one. Multiple locations, row34.com.
This Fort Point spot from the Island Creek Oyster Bar team is as much a serious beer bar as it is a seafood mecca. Maybe that’s why cult-followed breweries seem to celebrate special occasions here—think only-at-Row drafts from Bissell Brothers, Dieu du Ciel, and Upland Brewing. Beer director Suzanne Hays has saved deep cuts, such as cellared bottles from the dearly departed Pretty Things Beer & Ale Project, for past Sunday specials, but any day, it’s the best place for a rotating selection of fresh hops and food-friendly sours. 383 Congress St., Boston, MA 02210, row34.com.
With a stunning Carrara-marble bar along one wall and exposed wood beams and brick all around, this sleek Newburyport spot from the team behind nearby Ceia manages to be both a local hangout and a destination. Chef Justin Shoults's extravagant menu focuses on both land and sea—delicate sea-scallop ceviche with caviar, lime, and grapefruit; prime cuts of beef (the 16-ounce rib-eye is only for the brave…and hungry); and caviar service. Then again, if all you want to do is sit at the bar with a pint, a few pristine oysters, and a steaming bowl of pork-belly-studded clam chowder, that's just fine, too. 25 State St., Newburyport, MA 01950, brineoyster.com.
It could be the regular eruptions of the volcano in the Lava Lounge. Or the Sunday morning brunch, complete with a make-your-own-bloody mary bar. It could be the open kitchen jumping with live fire and young chefs wrangling large pieces of meat and fish. Maybe it's the pulled-pork sandwich with crunchy coleslaw and baked beans. But most likely, it's owner Chris Schlesinger's serious approach to having fun that makes the East Coast Grill a restaurant we're happy to head to—even if only to down a dozen briny, local oysters at the raw bar. 1271 Cambridge St., Cambridge, MA eastcoastgrill.net/.
Neither plain nor pretentious, this enchanting and candlelit treasure is a lesson in presenting good food with muted sophistication. Dishes including grilled salmon with tomato-tarragon butter or black-pepper pappardelle with chicken confit, fennel, and spinach, are as warm and agreeable as the earth-tone décor, while the bar menu shines with reasonably priced treats like frog legs with baby broccoli and oyster poboys. The room is cozy enough that finding a table on weekends can be competitive, but locals know the strawberry rhubarb croustada is worth lingering over. Besides, with such a lively bar, the wait is half the fun. 219 Elm St., Somerville, MA .
American Seasons co-owner Orla Murphy LaScola greets patrons with a charming Irish brogue as she seats them on the cool, inviting porch or in the warm, rustic dining room. Wherever they sit, they're in for a treat: Chef-owner Michael LaScola's creations—which include such delights as fried oyster and rare beef salad with mustard greens and orange, and blackberry-anise bomb—are seasonally inspired and beautifully executed. Dine here during a weekend getaway, and you'll soon find yourself studying ferry schedules just to plot your next feast. 80 Centre St., Nantucket Island, MA 2554, americanseasons.com.