Earnest Drinks
WHAT IT LOOKS LIKE: A steak and cheese. WHAT IT REALLY IS: Shaved and seasoned maitake and hon-shimeji mushrooms that are sautéed with peppers and onions, piled into a sub roll, and positively doused with gooey pimiento cheese. WHY TO GET IT: Besides the cheese sauce? Because it pairs perfectly with a boozy frappe made with scoops from the café’s sibling ice creamery, Gracie’s. 399 Binney St., Cambridge, MA 02142, orderearnest.com.
Brassica Kitchen + Café
Courtesy photo In its playful, never-ending quest to give the people what they want, Brassica has worn a dizzying number of hats this year: breakfast nook, provisions kiosk, empanaderia, fish taverna. Along the way, we worried fantastic menu fixtures like Brassica’s hot, made-fresh-daily doughnuts might get overshadowed. Judging by how quickly they sell out, our fears were misplaced. 3710 Washington St., Jamaica Plain, MA 02130, brassicakitchen.com.
Topsfield Drive-In
The Topsfield Drive-In at dusk. Courtesy photo Drive-in theaters, like any piece of real estate, are all about location, location, location. And there’s nothing like making new memories at this landmark fairground, a wide rural expanse that — when cars line up under golden sunsets and starry skies — looks straight out of the movies. Family-friendly films like Peter Rabbit 2 and blockbuster eye candy such as F9: The Fast Saga, meanwhile, are perfect for watching from an open hatchback. 207 Boston St., Topsfield, MA 01983, topsfielddrivein.com.
Tasting Counter
Ambitious. Playful. Revelatory. Sound like a theater review? Well, indulging in one of chef Peter Ungár’s nine-course tasting menus is a lot like sitting down for a critically acclaimed performance. And it truly is an immersive one, as ticket-holding diners get to watch the chef and his team cook and plate each intricate dish—seaweed-cured kampachi with shiitake custard, tender pork shoulder in a pool of fermented red chili curry—in the small open kitchen. Applause, please. 14 Tyler St., Somerville, MA 02143, tastingcounter.com.
Rectify Barbershop & Beauty Alcove
After amassing a loyal following at Love and Mercy salon in Boston, Dayna Gamba and her wife, Shalyn, a brow expert, have struck out on their own with this Mansfield beauty and barbering haven. Opened just last year, Rectify has fast become a go-to shop for those looking for a sharp cut and color or life-changing brow upgrades. rectifybba.com.
New Deal Fish Market
For almost a century, this family-run market has been culling ultra-fresh catch from its generations-deep relationships with suppliers at Boston Fish Pier. It shows in the shop’s unrivaled variety of rosy salmon fillets, fresh-caught sea bass, still-live sea urchin, and lusciously fatty fish collars. Unsure how to cook that head-on ocean perch? Let New Deal’s seasoned pros show you. 622 Cambridge St., Cambridge, MA newdealfishmarket.com.
Shred
Boston's fitness studios offer just about every workout under the sun. But to take SurfSet—a boot-camp-style class held on mock surfboards that simulates the feeling of being on water—you have to visit this three-year-old spot in Quincy. Once you finish blasting your core on the boards, head back to solid land for Shred's Spinning, reformer Pilates, and mat Pilates classes. 453 Washington St., Quincy, MA 2169, shredbody.com.
Dani Wagener, DW Beauty
Ever wonder how celebrities achieve that flawless red-carpet glow? It's all about the airbrush—makeup, that is. Boston beauty expert Dani Wagener, who's worked with Jenny McCarthy and Emily Deschanel, specializes in this technique. Armed with false eyelashes and the perfect lip color, she'll arrive at your prep site and promptly get about the business of making you look like a star. 326 A St., Boston, MA 02210, daniwagenerbeauty.com.
New Deal Fish Market
You can't get any fresher than this Cambridge spot: On any given day, you'll spot employees hauling out huge whole fish and breaking them down as you look on. Vast and unrivaled elsewhere in the area, the seafood selection includes whole branzino, Spanish octopus, and fresh anchovies—not to mention everything you need to make your own maki and sashimi. 622 Cambridge St., Cambridge, MA 02141, newdealfishmarket.com.
Bondir
With a fragrant wood-burning fireplace, country-chic décor, and refreshingly casual vibes, dining at this Area 4 gem feels like sharing an intimate home-cooked meal—only with much, much better food. Chef Jason Bond's elegant six-course tasting menus—think roast duck with tare, and milk custard with green tea and honeycomb—give you plenty of time to linger with your beloved, especially when you splurge on wine pairings. 279A Broadway, Cambridge, MA 02139, bondircambridge.com.
Alan Bilzerian
You're buzzed in the front door like it's a speakeasy, quickly greeted hello, and then given merciful room to roam. From Petrol-leather zip boots by Carol Christian Poell to handcrafted Italian cap-toe sneakers, Alan Bilzerian has your inner foot fetishist in mind when he curates his selection of stylish hoof art. 34 Newbury St., Boston, MA 02116, alanbilzerian.com.
The New School of Music
In one room, you might find tots trying to vocally or physically interpret instrumental sounds as part of the school's popular Dalcroze Eurhythmics program; in another, grade schoolers might be exploring the cultural roots of playground songs. Once they're hooked, sign them up for group or private lessons on instruments ranging from the piano to the didgeridoo. 25 Lowell St., Cambridge, MA 02138, newschoolofmusic.org.
Pini Swissa
Pini Swissa identified our hair dilemma immediately—lose the bulk around the crown that grows in bushy after a week, he advised. This is the man who styles Tom Brady, after all, so he should know. A close fade on the side nicely transitioned into a fuller top that looks great when styled with a bit of product, or parted and slicked for formal occasions. No one mistook us for Mr. Ba¼ndchen afterward, but we did receive a few long glances while strolling down Newbury Street. 18 Newbury St., Boston, MA 02116, piniswissa.com.
Nine Streets
Browse a fashion-forward selection of clothing, accessories, and home goods at Newburyport boutique Nine Streets. / Jim Brueckner, styling by Taylor Greeley New York transplant and former magazine editor Esther de Hollander curates an on-trend, off-the-beaten-path selection of clothing and accessories with just the right amount of wearable New England charm: classically but not cloyingly pretty, comfortable but not careless. Look for cult favorites such as Ace & Jig, Ilana Kohn, and Loup Charmant, plus interesting jewelry from upstarts like Meyelo, made by and benefiting Kenyan artisans. 40 Pleasant St., Newburyport, MA 01950, ninestreetsny.com.
The Red Wagon
When it’s time to outfit your progeny with knitted lobster sweaters and Holly Hastie dresses, look no further than the Red Wagon, Beacon Hill’s epicenter of pint-size prep. Thoughtful touches, like appearances by professional child-silhouette artists to immortalize those precious purchases, make the experience fun for parents and kids alike.