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Best Hotel, North

Beauport Hotel Gloucester

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North Shore beaches are relaxing—the parking, not so much. Enter the oceanfront Beauport Hotel, where you can extend your usual day trip through the weekend thanks to a glam rooftop pool; the fantastic 1606 Restaurant & Bar; and Gloucester Harbor cruises aboard the hotel's sister ship. As for the rooms? Think coastal cottage, with glorious balconies overlooking the water. When you're ready to venture off-property, grab one of the hotel's bicycles for an old-fashioned ride through town, or hop in a complimentary shuttle to Good Harbor Beach (our local fave) or anyplace else within a 3-mile radius. 55 Commercial St., Gloucester, MA 01930, beauporthotel.com.

Best Athletic Oasis, North

The Energy Barre

This North Shore micro chain has a motto: You belong here. And with a vast menu of classes beyond barre for exercisers of all stripes—from “abs and ass" to “mom + baby barre"—they deliver on that message. Each class offers a precise but non-intimidating goal (enhance cardio function, restore balance), demystifying the workout process for first-timers. Even more accessible? A large library of on-demand virtual courses for members who prefer to work out at a place (and time) of their choosing. Multiple locations, MA theenergybarre.com.

Best Place to Get Pampered, North

Briar Barn Inn

Photo by Kim Crawford

You can smell the salt air from the winding driveway at this micro inn, spa, and event space, which feels like a miniature version of Maine's Hidden Pond resort. The spa—its own annex, dimly lit and scented with sandalwood—offers muscle-melting massages from skilled staffers who clearly know how to listen: One visit and our problem areas were soothed. A pool available to spa guests and Grove, a farm-fresh restaurant where you can order up post-pampering rosé flights, make this spa day feel like a mini vacation. 101 Main St., Rowley, MA 01969, briarbarninn.com.

Best Jewelry Store, North

Royal Jewelers

Old-school, showroom-style jewelers still exist, at least in Andover: This bauble boutique within kissing distance of Phillips Academy stocks the heavyweights perfect for an heirloom grad gift—Bulgari, Cartier, David Yurman—but also specializes in small-town touches like watch repair and custom design. The shop itself, meanwhile, is friendly and warm, offering sparkle without the snoot. 58 Main St., Andover, MA 01810, royaljewelers.com.

Best Restaurant, North

Qué Mas

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Alex Pineda grew up in mom Lydia Shire's restaurants. Now he's a star in his own right: Having apprenticed under Wolfgang Puck and Heston Blumenthal, he recently unveiled a breezy new Latin-American hot spot that's enlivening downtown Beverly with a bubbly bar scene (including a killer spicy margarita); light and bright shareables (ceviche; sweet corn arepas); and surprising but not entirely unexpected twists (his mom's sherry-laced lobster stew). 114 Rantoul St., Beverly, MA 01915, quemasrestaurant.com.

Best Place to Grab a Drink, North

The Hidden Door

In an area renowned for nautical pubs and seafood shanties, this moody Marblehead speakeasy lends a touch of “Clue" mystique to the landscape. Here, drinks are works of art, served in glassware with more curves than Half Moon Beach. Consider the sour-cream-and-onion martini, a marvel of sour-cream-washed vodka and celery bitters, garnished with a chip. In winter, a stone fireplace filled with flickering candles adds to the ambiance. 259 Washington St., Marblehead, MA 01945, thehiddendoormhd.com.

Best Clothing Store, North

Charleston & Coco

If you've ever admired a stylish mom on the soccer sidelines and pondered her secret, here it is. Selling hip yet practical garb that touts hometown pride (the “Port" crop Ts are basically uniforms around here) as well as national heavyweights like Joe's Jeans and Seven for All Mankind at the vast denim bar, Charleston & Coco is the ultimate local boutique. The overall aesthetic is preppy chic, bringing a splash of Nantucket to Newburyport. 72 State St., Newburyport, MA 01950, charlestonandcoco.com.

Best Family-Friendly Activity, North

The Topsfield Fair

Photo by JOSEPH PREZIOSO/AFP via Getty Images

For more than two centuries, the Topsfield Fair has been an exemplar of simple family fun: The fall carnival offers infinite homespun charm, with an apple pie contest, a goat show, and even a Junior King and Queen Pageant where tots are crowned based on their conduct and personality. Oh, and what kid doesn't like thrilling (yet sturdy and well-monitored) rides and deep-fried Oreos, Twinkies, and PB&Js? 207 Boston St., Topsfield, MA 01983, topsfieldfair.org.

Best Place to Grab a Drink, South

Honey Baby

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The cocktails are the star of the show at this no-reservations Plymouth bar. Whether you're looking for predinner drinks or a nightcap, Honey Baby's menu delivers, from half a dozen different Old Fashioneds (of both the coffee and mezcal varieties) to martinis and refreshing sippers like the “Pretty in Pink," with rosé gin, basil, raspberry, and grapefruit soda. The bar has plenty of wine, beer, and mocktails, too—plus upscale, upbeat vibes that make us want to stay all night. 47 Court St., Plymouth, MA 02360, honeybabyplymouth.com.

Best Clothing Store, South

Assembly

It's hard not to leave with something you love from this multilocation boutique, which has been outfitting the South Shore since 2018. With looks for both men (knits from Theory, polos from Billy Reid, trousers from Paige) and women (denim from Agolde, dresses from the Great, bags from Bembien), its clothing is the epitome of quiet luxury. Need an extra hand while shopping? The boutique's private styling sessions are a must-try. Multiple locations, MA assemblyshowroom.com.

Best Jewelry Store, South

Long’s Jewelers

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When the occasion calls for something extra-sparkly, there's nothing like Long's—particularly the glittering new Braintree location, which opened in 2023 to much fanfare. Step inside the bona fide gem palace to find new, custom, and vintage jewelry, as well as a wide selection of watches. Bonus points for top-tier service—because an investment like this deserves the utmost attention. 150 Granite St., Braintree, MA 02184, longsjewelers.com.

Best Restaurant, South

Lê Madeline

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When executive chef Peter Nguyen promised “modern Vietnamese" cuisine at this 2024 revamp of the beloved Quincy noodle shop Pho Linh, he delivered. The flavor-packed menu blends Nguyen's second-generation Vietnamese upbringing with southern-inspired twists—think Viet-Cajun crawfish noodles, caramelized pork belly in fish-sauce caramel, and shrimp with creamy grits. Of course you'll come for the food, but expect to stick around for the creative cocktails and dessert (we recommend the cinnamon-chocolate lava cake). If you have room, that is. 409 Hancock St., Quincy, MA 02171, lemadeline.com.

Best Family-Friendly Activity, South

Treetop Adventures

Adventurous kids call, and TreeTop answers. Their feet are hardly on the ground at this “aerial adventure park" and ropes obstacle course in Canton as they swing on ziplines, balance on rolling logs, and maneuver across sky-high bridges (fully harnessed, of course). With 10 trails of varying difficulty, it's perfect for even the most timid kiddos and the bravest daredevils. We recommend the LED “Glow in the Park" night-climbing events for even more fun. 200 New Boston Dr., Canton, MA 02021, treetopcanton.com.

Best Hotel, South

Mirbeau Inn & Spa

No, it's not the French countryside—it's Mirbeau, where lush Monet-inspired gardens and architecture inspired by a Gallic manor house come together to create the perfect getaway. All rooms here come equipped with a fireplace, a soaking tub, and a memory-foam mattress, but the real amenities are outside the rooms—think complimentary fitness classes, a French-inspired bistro and wine bar, and outdoor poolside cabanas by the 16,500-square-foot spa. Bien joué! 35 Landmark Dr., Plymouth, MA 02360, plymouth.mirbeau.com.

Best Place to Get Pampered, South

Glow Beauty Boutique

No skin issue is too big or small for the beauty team at Glow, who will cleanse, hydrate, extract, wax, and tan you into the most primped and pampered version of yourself. Take the “Deluxe Glow" facial, which combines a peel with a deep, deep clean (cleansing, extractions, highfrequency disinfection with a glass wand) and a hydro-jelly mask that left us positively glistening in the sun on the way home. 351A Washington St., Braintree, MA 02184, glowbeautyb.com.

Best Athletic Oasis, South

Life Time

Part gym, part health and wellness destination, you could easily spend a whole day exploring all the nooks and crannies of Life Time's multistory complex in Westwood—from the two expansive training areas with every machine your heart desires to the hot tubs, saunas, café, recovery suite, and brand-new work-from-home space. Got kids? Keep 'em busy with complimentary childcare while you work out, or enjoy swimming together at the indoor and outdoor pools. 44 Harvard St., Westwood, MA 02090, lifetime.life.

Best Restaurant, West

XOXO Sushi

Photo by Joe St. Pierre

Who says you need to trek downtown for a proper celebration dinner? XOXO Sushi Bar brings the big-city energy straight to Chestnut Hill, where executive chef Kegan Stritchko (Uni, Fat Baby) serves up a serious omakase experience alongside playful creations like spicy bluefin hand rolls with aji amarillo, charred pineapple, and jicama that'll make you forget you're right outside a mall. The 16-seat stunning bar turns dinner into dinner theater, complete with sake and lychee martinis. The suburbs win again. 1154 Boylston St., Chestnut Hill, MA 02467, xoxosushi.com.

Best Clothing Store, West

Gretta Luxe

Girls' night out? Big meeting at work? Beachy vacation? Gretta's got a look for that. Fresh off a move to a new Wellesley space last spring, the store, owned by stylist to the stars Gretta Monahan, is fully stocked for every occasion you could imagine: think statement Isabel Marant vests, tailored Marni dresses, and breezy resort wear from Lemlem filling the racks. The accessories (designer shoes, custom charm bracelets) top it all off in supreme style. 97 Central St., Wellesley, MA 02482, gretta.co.

Best Athletic Oasis, West

Bosse

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What can make a day of pickleball even better? Well, let's see: How about pickleball and wood-fired pizza? Pickleball and personal training? Pickleball and party games? The buzz was palpable when this “pickledom" opened in the Natick Mall's former Neiman Marcus space this past November, and so far, it's lived up to the hype. While the ever-popular racket sport is the star of the show across 21 courts, this is more than just a sports club; it's a destination for anyone who enjoys good food (in this case, from top chef Chris Coombs) and fun. 310 Speen St., Natick, MA 01760, bosse.net.

Best Hotel, West

Inn at Hastings Park

After a big spring celebrating the 250th anniversary of the Battles of Lexington and Concord, this Relais & Châteaux inn is now back to its regularly scheduled programming: hosting ultra-luxe stays with a dash of history. Guest rooms, spread out over three 19th-century buildings, come with high-thread-count Matouk linens, Molton Brown amenities, and thoughtful design touches (opt for the “Sam the Minuteman" package to secure an in-room fort for the littlest adventurers). But our favorite part of the inn has to be the dining program: Led by L'Espalier and American Seasons alum Alissa Tsukakoshi, Town Meeting Bistro and the gorgeous, green Culinary Garden are ideal places to sit back, relax, and soak up the past and the present 2027 Massachusetts Ave., Lexington, MA 02421, innathastingspark.com.

Best Jewelry Store, West

Date & Time

Photo by Michael Blanchard

When you're investing in a new heirloom watch or a diamond necklace, you deserve more than a miniature bottle of water. That's why this fine-jewelry mecca has its own bar, lounge, and café where customers can kick back and relax after perusing the likes of Rolex and Tudor watches and sparkling Pomellato statement pieces you'd be hard-pressed to find elsewhere. We also love the fun events the store occasionally puts on, such as May's “Cars & Coffee" with SR Auto Group—the perfect excuse for connoisseurs of the good life to connect and celebrate. 5 Concord Rd., Sudbury, MA 01776, dateandtimema.com.

Best Family-Friendly Activity, West

Roller Kingdom

Imagine the roller rinks of yore—neon lights, thumping pop music, and the vague scent of snack-stand hot dogs wafting through the air. That place still exists in Hudson, and we can't get enough: Open since 1979 and still going strong, Roller Kingdom is an old-school skating destination for modern kids, with extras like laser tag and an arcade extending the fun. We particularly appreciate the $1 admission fees on Wednesday nights ($3 skate rentals) for the throwback prices, too. 5 Highland Park Ave., Hudson, MA 01749, rollerkingdom.com.

Best Place to Get Pampered, West

Guerda Massage

Shhh…we'll let you in on a little secret. The best massage in MetroWest can be found in a tiny gray building on River Street in Wellesley. An alum of pampering palaces such as Grettacole Beauty and Bella Santé, massage therapist Guerda Paul excels at tried-and-true styles such as deep-tissue and Swedish, but we also appreciate her more-specialized offerings, from fibromyalgia and cancer-relief to pregnancy- and sport-focused massages. Add on a facial to give yourself the ultimate glow-up. 47 River St., Wellesley, MA 02481, guerdamassagetherapy.com.

Best Place to Grab a Drink, West

GlenPharmer Distillery

The drinks arrive in a glass cloche. As the server removes the top, the billowing smoke wafts around your table mysteriously. This is the part of GlenPharmer's cocktail menu dubbed “The Smoking Section," and it's fabulous. Of course, that's not the only reason to visit this Franklin “grain to glass" distillery. Mai tais, margaritas, and espresso martinis are all blended with GlenPharmer's signature spirits, as are more-creative libations such as a recent sweet-spicy “Yuzu Bonfire," made with the award-winning ghost-pepper vodka, yuzu, agave, and grapefruit soda—best enjoyed on the repurposed covered bridge for extra ambiance. 860 W. Central St., Franklin, MA 02038, glenpharmer.com.

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