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/.
Four years in, the Nautilus still has the hottest tables in town—no surprise given the trifecta of talented folks behind it. Chef Liam Mackey combines local seafood with Asian and Latin flavors in inspired small plates such as tempura oyster tacos wrapped in nori, while wine director Stephen Bowler curates a deep, Wine Spectator–lauded list that includes rare reserve vinos by the glass. And Culinary Institute of America–trained bar manager Clinton Terry draws on his background to craft mouthwatering cocktails featuring herbs, spices, and foams. Come summer, only day-of reservations are accepted—hurry, phone lines open at 1 p.m. 12 Cambridge St., Nantucket, MA 02554, nautilusnantucket.com.
While it’s hard to unwind these days, this luxe resort is making it a little easier to get some much-needed R & R. Extra pre- cautions—including contactless golf-cart pickup, grocery-delivery service, and reduced capacity at pools and at Ocean Edge’s private beach—provide peace of mind, while new private experiences such as beach yoga and oyster tours make it easy to practice social distancing while giving the kiddos an unforgettable adven- ture. So go ahead, book that luxurious mansion suite. Boozy mudslides delivered straight to your beach chair await. 2907 Main St., Brewster, MA 02631, oceanedge.com.
Raise a glass, if you will, to the ever-stunning Oak Bar. It's where sex appeal takes its post-prandial drink, where intimacy lounges in a long, cool black dress. It's where fascination sips a stiff Manhattan. There are mere mortals here, too, in everything from Levi's to tuxedos, huddled in conversation with one another, raiding the cigar-stocked humidor, slugging oysters from the raw bar, and soaking up the live jazz that oozes through the intricately detailed room. No matter who's filling it, the Oak Bar is simply one of the New World's most intoxicating Edwardian settings. 138 St. James Ave., Boston, MA fairmont.com/copley-plaza-boston/dining/oak-long-bar-kitchen/.
The dish is hot crab-and-cheese dip, and it goes a little something like this: chunks of tender, sweet blue crab tossed with heavy cream and supersharp cheddar, then wood-fired to a roof-of-mouth-scorching sizzle. After that, the menu at this guilty-pleasure oasis is your oyster. Or your goat cheese-slathered wild mushroom pizza. Or your flaky chicken potpie with a scrumptious baked side of three-cheese macaroni. The elegant setting is so picturesque you could have your wedding reception here—so long as you let out the dress first. 1217 Main St., Hingham, MA 2043, scarlettoaktavern.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.