Tupelo
The reserved atmosphere may be more Cambridge than New Orleans, but Tupelo's southern flavors are right on. Owners Mike Walker and Renee McLeod serve authentic comfort-food classics like creamy pimiento cheese (the caviar of the South), hearty gumbo, and crunchy fried crawfish tails. The crown jewel? Alligator prepped the way God intended: coated in buttermilk batter, hot sauce, and Cajun spices, and piled on a bed of creamy cheddar grits. 1193 Cambridge St., Cambridge, MA 02139, tupelo02139.com.
Community Ice Skating @Kendall
For those who find the idea of muscling their way into a frozen mosh pit deeply unappealing, think of Kendall Square's rink as an antidote to the madness of the Frog Pond: a place where you can find low-key winter thrills, with plenty of Zamboni action to ensure smooth glide time. Warm up with an après-skate cuppa at Voltage, or a more-adult beverage at Firebrand Saints. 300 Athenaeum St., Cambridge, MA 02142, skatekendall.com.
The Big Quiz Thing at Oberon
Bar trivia is a tricky business, but the Big Quiz Thing has the formula down. The free monthly event at Oberon offers kitschy graphics, quirky categories, and appropriately mind-lubricating beverages. Hence, it's the closest analogue to a game show on Boston's nightlife circuit, right down to the final round, where high-performing teams square off in a sudden-death buzzer challenge. 2 Arrow St., Cambridge, MA 02138, bigquizthing.com.
Alton Lane
With a mounted deer head and a sleek bar stocked with craft beer and liquor, Alton Lane’s showroom has all the trappings of a man cave—if said man cave also proffered bespoke suiting with thousands of fabric and design options. Be sure to take a spin in the 3-D body scanner; it captures more than 100 measurements in 30 seconds to ensure the perfect fit. 91 Newbury St., Boston, MA altonlane.com.
Lash L’Amour
So long, lackluster lashes and sparse brows: Lash L’Amour’s specialists have easy fixes for bigger, better volume. For over-tweezed arches, a set of eyebrow extensions restores original glory. For next-level flirting, a volume extension treatment, which isolates individual hairs and allows up to 500 ultrafine extensions per eye, will have you batting those lashes in no time. 129 Newbury St., Boston, 617-247-1871; 55 Langley Rd., Newton, 617-916-1209. 129 Newbury St., Boston, 02116, lashlamour.com.
Union Street Inn
Co-owner Ken Withrow spent 20 years working for famed hotelier Ian Schrager, and the in-town inn he runs with his wife, Deborah, puts that pedigree on full display, from staffers trained to remember your name and wine preference to guest rooms featuring Frette bedding and free, strong WiFi. It’s also the only island B & B to offer made-to-order breakfasts, though individual tables mean you needn’t get chummy with fellow guests. 7 Union St., Nantucket, MA 02554, unioninn.com.
Boston Calling
Okay, so maybe this isn’t a surprising choice. But when a three-year-old music festival is already bringing the likes of Sia and Janelle Monáe to our fair town, we must tip our hats. The band choices are solid, and there’s actually enough space for food, fans, and giant Jenga. With a big move to Allston planned for next year, we can’t wait to see what Boston Calling will bring to the city next. bostoncalling.com.
H.O.P.E. Inc.
Forget tepid evenings of meek verse and golf-clap applause. H.O.P.E. Inc.’s poetry is a full-contact sport. Every month at Dudley Café, the group’s performers work the room, spitting raw rhymes. The audience explodes in applause at particularly pleasing verbal gymnastics—sometimes even chanting along—between bites of soulful cuisine dished out by global street-food pop-up Chop Bar. 15 Warren St., Roxbury, MA 02119, dudleycafe.com.
Vizio Optic
At this Brookline Village eyeglass emporium, you’ll be greeted by the brands you know and love (Chanel, Ray-Ban), and delighted by new-to-you lines (funky German-made specs by Wissing; colorful pairs from Woow with motivational sayings on the temple tips). Staffers are helpful, steering you toward the well-fitting frames you simply can’t leave without. 11 Harvard St., Brookline, MA 2445, viziooptic.com.
Follain
This pretty, well-appointed South End apothecary caters to your beauty needs, but with a conscience. Owner Tara Foley selects only the healthiest and most environmentally friendly products, including locally made goods from Shamanuti, Farmaesthetics, and Amber Blue, to line her shelves (an in-store hand-and-body-soap bar for refills cuts down on plastic bottle waste, too). Foley’s even committed to your well-being on vacation: Her Nantucket outpost opened this past May. 53 Dartmouth St., Boston; and 9A S. Beach St., Nantucket, shopfollain.com.
The Proprietors
Local ingredients get the global treatment at Michael and Orla LaScola’s newest venture. To wit: addictive "Pork-Umms," which star shaved Berkshire pork, scallions, and sesame barbecue sauce on a kimchi biscuit, and the silky clad verde soup, made with parsnips and topped with marinated octopus, cornbread croutons, and smoked paprika. The well-traveled flavors also extend to the bar, where adventurous drinks are mixed with pico, shōchū, tamarind, quinoa vodka, and—believe it or not—killer bee pollen. 9 India St., Nantucket, MA 2554, proprietorsnantucket.com.
Fog Island Café
There’s no wine list or fancy raw bar at this laid-back local institution—just bottomless cups of joe from Nantucket Island Coffee Roasters and heaping platters of granola-and-banana pancakes to cure whatever ails you. Still hankering for a little hair of the dog? The BYOB eatery can serve up a virgin bloody mary ($5) for your mixing pleasure. 7 S. Water St., Nantucket, MA 2554, fogisland.com.
Mr. Sid
With an on-site bar and hair salon, this been-around-forever store is the sharp-dressed man’s antidote to crowded malls and big-box suit stores. Whether you’re the kind of guy who skews custom or the type who prefers a quick and painless shopping trip, the experienced sales consultants and tailors here will make sure you leave with sophisticated threads that fit to perfection. 1211 Centre St., Newton, MA 2459, mrsid.com.
Vows
We can't think of a bigger nightmare than lining up with thousands of grabby, frantic bargain dress hunters à la Filene's Running of the Brides. Fortunately, Vows is packed with designer gowns from the likes of Monique Lhuillier, Reem Acra, and Pronovias at steep discounts. And with a recently added accessories selection that includes bags, jewelry, and shoes, getting the head-to-toe look for less is a thoroughly civilized endeavor. 130 Galen St., Watertown, MA 2472, bridepower.com.
The Altered Bride
Looking for iridescent ivory gloves? They're here. Need a pearl-encrusted purse to match? Bingo. Women of all ages and income brackets find themselves completely taken with the personal, knowledgeable service of this elegant Back Bay bridal boutique and ecstatic over the trimmings for sale—custom-made veils and tasteful tiaras, delicate satin shoes, and lace and mink garters. 376 Boylston St., Boston, MA .