Wally’s Cafe
Photograph by Jared Kuzia From the outside, Wally’s looks like your average anonymous dive. But the drab exterior belies its storied history: This place has put live jazz acts on stage 365 days a year since 1947. Squeeze in among the regulars, order a beer, and get ready for top-notch jazz, funk, or Latin jazz salsa right up until the joint shuts down at 2 a.m. 427 Massachusetts Ave., Boston, MA 02118, wallyscafe.com.
Jack’s Abby
With its growing canned line, 175-seat restaurant serving everything from wood-fired pizzas to beer-braised mussels, and charming new Framingham facility capable of producing 100,000 barrels a year, Jack’s Abby epitomizes the modern American brewery. But at the end of the day, it’s still about the beer, and Jack Hendler continues to push the boundaries of the lager style, producing dozens of exceptional smoked, soured, and sessionable varieties. 100 Clinton St., Framingham, MA 01702, jacksabby.com.
Armando’s
Photograph by Kelsey Cronin The DiPaolo family’s metal-deck magicians continue to churn out crisp yet pliable New York–style pies, all blanketed with house-made red sauce. Grab a cold can of grape soda, bask under the plastic glow of Little League placards along the wall, and raise a greasy slice to a half century of West Cambridge history. 163 Huron Ave., Cambridge, MA 02138, .
Moonshine 152
To fry up the greatest golden bird in Boston, chef Asia Mei eschews thighs and breasts in favor of the lowly wing. Butchered in-house, dry-brined in a secret spice rub, and marinated for two days in a pool of buttermilk and herbs, the meat melts off the bone. Add in the delicate crust and side of poblano-laced ranch dressing, and you have the epitome of southern-fried goodness. 152 Dorchester Ave., South Boston, MA 02127, moonshine152.com.
River Gods
Editor's Note, July 11, 5 p.m.: River Gods has announced that they are permanently closed. It’s not the fine pour of Guinness or the cocktail list. It’s not the wooden thrones or the whimsical décor. It’s the music. Rather than crank out an iPhone playlist determined by algorithm, River Gods hosts DJs who spin soundtracks worth drinking to. 125 River St., Cambridge, MA 02139, rivergodsonline.com.
Chatham Bars Inn
Sweeping oceanfront views and luxe accommodations (did someone say spa butler and private beach?) are par for the course at this classic resort. But the Chatham Bars Inn is always a step ahead. Produce is sourced from its 8-acre farm. The spa overlooks Japanese rock gardens. Tired of boating and swimming? Pay a visit to the lush croquet court. And if you ever need to leave the resort, just borrow a house Lexus with unlimited miles. 297 Shore Rd., Chatham, MA 02633, chathambarsinn.com.
White Elephant
Leave your car on the Cape. Nantucket’s iconic harborfront resort, and its well-appointed rooms, are no more than 10 minutes from anyplace you’d want to go: Young’s for bikes, the Juice Bar for ice cream, the beach and ferry, too. And if you’re looking for the best on-island massage, you don’t even have to leave the building. 50 Easton St., Nantucket, MA 02554, whiteelephanthotel.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.
20byNine
Courtesy Photo Martha’s Vineyard is known for many things, from crispy fried clams to breathtaking beaches. But top-notch craft-cocktail bars wasn’t one of them—that is, until 20byNine came along. You can’t go wrong with a Manhattan, which comes close to the classic drink’s platonic ideal. After just one, you might be bold enough to cozy up to your bartender and ask for that day’s “smash,” a rotating off-menu creation. 16 Kennebec Ave., Oak Bluffs, MA 02557, 20bynine.com.
Havana Club
Never danced a step in your life? No problem. This Central Square club holds $12 salsa lessons every Friday and Saturday at 9 p.m., plus bachata lessons on Mondays at 8 p.m. You’ll look like a pro by the time the real party begins, with more than 300 dancers burning up the floor from 10 p.m. until 2 a.m. 288 Green St., Cambridge, MA 02139, havanaclubsalsa.com.
The Banshee
Make sure someone on your quiz team checks Twitter before the games begin: Host Mark Daly always provides a few hints for social-media-savvy smarties. His questions run the cultural gamut, from celebrities to geography, sports to current events, and even music, with an audio round worth double points. A monthly tournament offers higher-stakes prizes, while every Wednesday night offers a new chance to win generous gift cards. 934 Dorchester Ave., Dorchester, MA bansheeboston.com.
Porchfest
West African drummers, punksters, Bollywood funksters, and space rockers, all jamming out on porches, patios, and more across Somerville. This outdoor festival just might be the only time all year that you’re going to be happy to hear your neighbor play the guitar. With copies appearing in Jamaica Plain, Roslindale, Arlington, and at the Lawn on D, it’s clear the fun(k) is now infectious. somervilleartscouncil.org/porchfest.
Danger Booth
Photograph courtesy of Zac Wolf When it comes to giving your guests custom photo keepsakes, it's best to think outside the box—or, in this case, the booth. Danger's open-air, freestanding unit (complete with a touchscreen, flash, and printer) can be as civilized or as crazy as you desire, with photo-fun experts on hand to hem a themed fabric backdrop, print out a step-and-repeat, or even hook you up with a designer for one-of-a-kind scenery. Move over, Instagram. thedangerbooth.com.
AE Events
Planning a wedding is like putting together a 1,000-piece puzzle, and the six-person team at AE Events is skilled at making it all fit. Want a seven-course Tuscan feast with live jazz for 400? Done. A 50-person bonfire beach celebration? No problem! From contracts and vendor negotiations to creative extras (taco bar, anyone?), they're steadfast, organized allies. And if your budget is a ball and chain, they'll work with that, too. 546 East Broadway, South Boston, MA 02127, aeevents.com.
Forklift
Mediterranean, Asian, classic American—this Union Square caterer will happily hop from cuisine to cuisine for your wedding spread, incorporating vegan and gluten-free menus with ease. Chefs Dennis Tourse and Jamie Rogers are tight with local farmers, which translates to personalized menus featuring natively sourced ingredients whenever possible. Top requests include avocado beggars' purses and fava-bean crostini with wild mushrooms. 5 Sanborn Ct., Somerville, MA 02143, forkliftcatering.com.