Brian Mercury, Oak + Rowan
Since earning this accolade four years ago, Mercury has somehow managed to up his game even further in his current role at Oak + Rowan. His beguiling confections are at once adventurous and familiar (see: the Twix-inspired sweet with chocolate cremeux, whey caramel, and a bright-green pool of EVOO). And Mercury’s deft touch extends far beyond the dessert menu, from his outstanding sourdough bread to the irresistible pastry cart at brunch. 321 A St., Boston, MA 02210, oakandrowan.com.
Ocean Edge Resort & Golf Club
The hardest part of a vacation is making sure everyone has a good time. At Ocean Edge, however, that’s never a problem. Looking to work up a sweat? Swing a club or paddle a kayak. Need to entertain the kiddos? Keep ’em busy with kite-making and scavenger hunts. Longing for some time all to yourself? Lounge on the private beach or check into the spa. No matter how you spend your trip, you’ll want to find time at sunset to roast s’mores ’round the beach fire. 2907 Main St., Brewster, MA 02631, oceanedge.com.
Meredith Bonner, Barneys New York
Bonner is like the fashionable friend you wish you could bring along on every shopping spree: patient; quick with a joke to enliven fitting-room tedium; and known to go great lengths to find the perfect pair of jeans. The best part? Getting whisked away to her cozy office to try on your haul in blissful privacy. Copley Place, Boston, MA barneys.com.
House of Blues
A GA ticket to House of Blues means A) you’re seeing one of your favorite acts, and B) you’re about to move. We love House of Blues for the energy on the floor, whether you’re dropping it low with Lizzo, moshing with August Burns Red, or crying as you hold an iPhone in flashlight mode aloft with Jenny Lewis. Hey, however the music moves you is cool with us. 15 Lansdowne St., Boston, MA houseofblues.com/boston.
Trina's Starlite Lounge
The H-word may be ill defined—something about young, vaguely cool people having fun in a place where you're not. Unless you happen to be at Trina's. Equal parts dive bar, cocktail lounge, diner, and comfort-food joint, it has the type of lived-in authenticity the you-know-whats can't resist. 3 Beacon St., Somerville, MA 02143, trinastarlitelounge.com.
Kitchen Kibitz
Perhaps because it aligns with our modern taste for all things fermented, preserved, and pickled, Jewish cuisine is undergoing a much-needed renaissance in these parts. Playing a big role in its revival is this recurring pop-up from proprietor Jeff Gabel, who's managed to talk culinary luminaries like Bread & Salt Hospitality's Joshua Lewin into getting creative with everything from brisket-topped latkes to hamantaschen. kitchenkibitz.com.
Courtside
Karaoke at this Cambridge dive can be a Darwinian proposition—despite Courtside's rec-room feel, every singer's out for herself on Thursdays, Fridays, and Saturdays. But that's part of the fun. Lubricated by cheap pitchers of beer and egged on by crowds that only get feistier as the night wears on, singers who take Courtside's "stage" revel in their four-ish minutes of glory, leaving the next person itching to try to win over the room with even larger antics. 291 Cambridge St., Cambridge, MA 02141, courtsidekaraoke.com.
Once Somerville
It's definitely not a bar, though there's no shortage of beers. And it's not exactly a concert hall, but it knows how to pull in national acts and put on one hell of a show. Welcome to Once Somerville, a 9,000-square-foot venue of shape-shifting entertainment. Whatever happens to be on the calendar—Monday-night tacos, heavy-metal yoga, storytelling performances from the Moth—it's sure to beat the regular routine of draining a few pints at your local watering hole. 156 Highland Ave., Somerville, MA 02143, oncesomerville.com.
F1 Boston
Tired of the humdrum pace of that 9-to-5 lifestyle? Head out to Braintree to show the world you’re really the next Danica Patrick in training. Sure, you’ll be driving a go-kart at a slower speed than the average grandmother, but once you’re clad in an actual racing jump suit, helmet on, whipping around the indoor track, you’ll swear you’re ready for the big leagues. Hairpin curves and an endless series of Days of Thunder references await. 290 Wood Rd., Braintree, MA 02184, f1boston.com.
Paradise Rock Club
No venue in town outdoes the 'Dise, where stellar acoustics and a wide-open layout ensure that music lovers get both an earful and an eyeful from just about anywhere on the floor. National indie acts like Tapes 'n Tapes and the Kooks frequently pop up on the bill, alongside buzzy local bands such as Bon Savants and Aberdeen City. The fact that bona fide legends (Blondie, Tom Petty, the Pixies) have performed here certainly doesn't hurt the vintage-cool, never pretentious, vibe. 967 Commonwealth Ave., Boston, MA thedise.com.
Bronwyn
Blutnudeln. Reibekuchen. The former translates to chewy wheat noodles laced with braised beef and, yes, pig’s blood, the latter a crisp potato pancake that’s topped with tart rhubarb chutney. With his second restaurant, the French-trained, German-American chef Tim Wiechmann has not only put his stamp on German and other Eastern European cuisines, he’s also introduced the city to an entirely new, and entirely delicious, vocabulary (not to mention some epic, face-size soft bretzels paired with horseradish mustard). 255 Washington St., Somerville, MA 2143, bronwynrestaurant.com.
Julie Erickson, Endurance Pilates and Yoga
With 20 exercise and teaching certifications, Julie Erickson certainly has the cred. But education alone doesn’t make a great trainer. Erickson’s technique is very hands-on—she’ll tell you exactly what parts you’re strengthening and why while she works with you in her Arlington studio. Erickson has also selflessly donated her time and energy to help victims of the Boston Marathon bombings regain their strength. 446 Massachusetts Ave., Arlington, MA 2474, endurancepilatesandyoga.com.
No. 9 Park
Chalk it up to the anticipation of an unforgettable meal, the warm reception proffered at the host stand, or maybe just the impact of that briskly shaken craft cocktail in your hand. Whatever the reason, there's something so magical about No. 9 that your date suddenly seems to have gotten infinitely more attractive. And just wait till you try what Barbara Lynch's kitchen has created that day, be it sturgeon with pork belly en papillote, or a chocolate cream tart with saffron and grapefruit—two spoons, of course. 9 Park St., Boston, MA 2108, no9park.com.
The Oak Room
Some hotel bars are trendy watering holes with rooms upstairs; others are mediocre places for conventiongoers to pickle themselves. The Oak Bar is another species entirely: an escape that's equal parts time machine (jazz piano; career bartenders doling out snack mix) and glorious splurge ($17 martinis delivered in an icy shaker; a Chateaubriand sandwich on brioche). 138 St James Ave., Boston, MA 2116, oaklongbarkitchen.com.
David Ives
The president of WGBH will do anything to solicit a buck for Channel 2; luckily for his audience, he's got a class act. At a Boston Pops fundraising special last spring, Ives took on Gilbert and Sullivan, singing innumerable verses of "I Am the Very Model of a Public TV President" to the tune of "Modern Major General"; it was a high point in the history of panhandling. MA