The Dog Bar/65 Main
Folks who come to this beloved local watering hole enjoy its outdoor patio and live music on weekends, and get an added bonus: They can walk into the adjoining restaurant, 65 Main, and pair the town's best burger with, say, a pint from Cape Ann Brewing Company. 65 Main St., Gloucester, MA dogbarcapeann.com.
Gus & Ruby
Rodeo & Co. Photography Why flip through book upon book of invitations when you can have something that’s completely, uniquely you? That’s exactly what you’ll get when you commission Samantha Finigan and Whitney Swaffield, of Gus & Ruby, to create custom paper goods for your party. The New Hampshire&ndashbased duo, who launched a long-awaited brick-and-mortar on Beacon Hill last October, demonstrate a particular flair for the unexpected. Exhibit A: their recent Bridgerton-inspired invitation suite, which paired Victorian silhouettes with modern script and gold foil. 99 Charles St., Boston, MA 02114, gusandruby.com.
Matt Murphy's
Some might scoff that Matt Murphy's perennially wins this award because, well, there aren't exactly Irish restaurants on every corner of this largely Irish town. That probably just means they haven't tasted the sausage, beans, and mashed potatoes with a hint of anise. Or sipped a perfect pint of Guinness while devouring fish and chips wrapped in the morning paper and accompanied by chunky, homemade ketchup. This Brookline Village hideaway is still an unadorned pub experience: good people (Jason Waddleton is one of the friendliest waiters in the Boston area), live seisiuns, or sessions of traditional Irish music, and food that's proud to call itself—dare we call it—Irish cuisine. 14 Harvard St., Brookline Village, MA mattmurphyspub.com.
Hangar B Eatery
A top-notch brunch spot—on a tarmac? It's long been a reality in Cape Cod, where chef Brian Erskine turns out fluffy lemon-ricotta pancakes and hearty red-flannel hash from a kitchen at the Chatham Municipal Airport. Summer weekends find the place jam-packed, but you can pass the wait time on the second-floor deck watching the biplanes coming and going. 240 George Ryder Rd., Chatham, MA 2633, hangarbcapecod.com.
Leather World
Leather World A local stalwart for more than 40 years, Leather World helps us handle our hauls, supplying a polycarbonate spinner to withstand the perils of the TSA, a leather duffel perfect for that weekend jaunt down to the Cape, and a trim briefcase for the daily commute to and from the office. Plus, all of its locations offer one line of embossing at no additional cost. 30 Brattle St., Cambridge, MA shopleatherworld.com.
Jim Horgan
Front Street's bar (260 Berkeley St., Boston) is a quiet, secure haven, protected by Horgan. A five-year veteran of the bartending wars of Boston and Cape Cod, Horgan knows his regulars and what they drink, and he protects their privacy. "This isn't a pickup bar," Horgan says. "People come here to relax. Single women come in by themselves and trust me to see they're left alone. People know that no one will bother them here." Front Street, 260 Berkely St., Boston, MA .
Orleans Inn
As the only waterfront restaurant in town, the Orleans Inn has reason to brag. But humble's the default setting at this 132-year-old spot above Town Cove, which has gone through many an incarnation (boarding house, supply store) to reach its current status as the top place to gaze and graze on the Cape, with a dining room serving up local seafood with stirring vistas. 3 Old Country Rd., Orleans, MA 2653, orleansinn.com.
Coonamessett Inn
With its glossy, red shingles and gabled roofs, the Coonamessett Inn is the epitome of old Cape Cod, a perfect setting for high-style weddings and anniversaries alike. But you needn't wait for a special occasion: Sunday brunch features an array of delicious classics, from make-your-own omelets and baked salmon with special weekly sauces like beurre blanc or citrus, melon, and mango, to oversized fruit plates and gorgeous renditions of sweet favorites like chocolate mousse and carrot cake. 311 Gifford St., Falmouth, MA 2540, capecodrestaurants.org.
The Naked Oyster
Manhattan meets Cape Cod at this trendy Hyannis bistro and raw bar. The oysters—prepared naked or topped with a hint of cocktail sauce, a splash of Absolut Peppar vodka, or sour cream and caviar—are beyond divine. The littleneck clams are tiny tastes of the sea. And the melt-in-your-mouth beef carpaccio appetizer and a host of tempting desserts round out a fun, fresh menu. 20 Independence Dr., Hyannis, MA nakedoyster.com.
Truro Beach
This gorgeously untarnished world of sweeping dunes and fresh Atlantic air is about as idyllic as nature gets. That may seem to be true of many Cape shorelines, but this one stands out from others for its spectacular and endless stretches of perfectly undisturbed white sand. With nary a touch of human architecture for miles, this slip of coast also provides a view of the sunrise that approaches the sublime. Rte. 6, Truro, MA .
K. Kerkorian Weddings & Events
For more than a decade, we’ve watched Kristyn Kerkorian climb the ladder of local event planning, following along as she went from helming catering sales at the Colonnade Hotel to throwing parties for the Red Sox to launching her own wedding-planning firm in 2017. But it’s not just the BU alum’s prestigious pedigree — or the fact that she successfully executed eight COVID-era celebrations — that stands out to us. We’re equally taken by her calming, down-to-earth demeanor (a godsend for anxious brides and grooms) and undeniable gift for design, evident in each meticulous tablescape, escort-card display, and floral arrangement she helps envision. kkerkorianevents.com.
The Maids
We aren't ones to cry over spilt milk, as our floors can attest; our couch has more hair on it than our cat. Without a speck of judgment, the Maids clean up our act month after month, dusting baseboards, degriming showers, and all but eliminating any traces of pet (except for, of course, the pet itself). They're quick, well priced, and unobtrusive: Aside from the preternatural sparkle and neatly triangled toilet paper, you'd never know they'd been there. maids.com.
Appleton Bakery
It's hard to decide what's best about this cozy South End bakery, where the owners have thought of every amenity for busy city dwellers. Is it the a.m. treats? The lunch? The cute tables that overlook Appleton Street? The gourmet take-out options? The catering? When push comes to shove, we choose the scandalousy delicious breakfast goodies: scones to cry over, fruit-studded muffins, old-fashioned sour cream coffee cake, and granola that could put a commune out of business. We could go on, but our trainer says no. 123 Appleton Street, Boston, MA appletoncafe.com.
The Maids
Amid a flurry of cleaning services catering to on-the-go urbanites, the Jamaica Plain outpost of this national operation shows an unbeatable blend of polish and professionalism. After setting the appointment and sending an e-mail confirmation, your cleaning team will arrive armed with grime-busting equipment and a dozen sprays, as well as a rigorous 22-step plan for restoring your home's sparkle. The Maids will even pick up and drop off your keys at work—another excellent reason to fork over the $159 fee, which is lowered if you book monthly follow-ups. 179 Boylston St., Jamaica Plain, MA 2130, .
Scribe
This is just to say that the apology note you left on the fridge didn't quite cut it, and the person whose sweet, cold plums you scarfed down is profoundly annoyed. Next time, put those words of remorse—or thanks, or affection—on something that gives them a bit more weight. At cornucopian paper shop Scribe, choose from scores of distinctive cards (Smudge Ink, B Designs) and refined stationery from the likes of Boatman Geller. If a gift is required, there are fragrant Seda France candles, Heather Moore jewelry, plus purses, pens, and more. (But sorry: no replacement plums.) 84 Washington St., Marblehead, MA 1945, .