JUNE
May 31-June 2
If you go:
Philadelphia
2 hours by car
1.5 hours by Amtrak
For beer lovers, Philly is the city of brotherly suds. From May 31 through June 9, 261 beer-centric bars, breweries, and restaurants band together for the sixth annual Philly Beer Week (phillybeerweek.org). Events include a beer expo, barbecue block party, and, on June 2, Craft Beer Day on South Philly’s booming Passyunk Avenue. Drop your luggage at the new Hotel Monaco (from $319; monaco-philadelphia.com), and it’s a swift stroll to the nearby Independence Visitor Center’s Opening Tap festival. Forty-five bucks buys access to more than 30 of the region’s best beer-makers, including newcomers Round Guys and Free Will. Afterward, head to handsomely renovated restaurant Fork (306–308 Market St.; 215-625-9425), where Torrisi vet Eli Kulp turns out New American dishes like crab-apple soup and Sichuan-peppercorn-glazed duck, followed by funky, multifloor Strangelove’s (216 S. 11th St.; 215-873-0404) for lemon icebox cream pie and one of eighteen pedigreed drafts from cultish breweries like California’s Russian River.
If you stay:
Brooklyn’s edgiest dance label, L.I.E.S., closes out Red Bull Music Academy’s monthlong residency (redbullmusicacademy.com) on May 31, as part of a stacked bill at Williamsburg’s Output. On June 1, Chicken and Beer (chickenandbeer.org) takes over (Le) Poisson Rouge with b-boy battles and bottomless hops and hot wings. Also mixing meat products and music is DayLife (lowereastsideny.com), a June 2 outing that blankets three blocks of Orchard Street with AstroTurf, yoga classes, D.J. lessons, a pastrami-eating contest, and pushcart versions of LES staples like the Fat Radish and Mission Chinese.
June 7-June 9
If you go:
Falmouth, Cape Cod
4 hours by car
In the 1800s, Falmouth was the third-largest whaling port on the East Coast. Today, the resort town has a thriving local food scene—making it the perfect backdrop for the inaugural Cape Cod Food & Wine Festival (June 8; tickets from $65; Barnstable County Fairgrounds, 1220 Nathan Ellis Hwy.; capecodfoodwine.com). The event’s back-to-back four-hour tasting sessions are strictly 21-and-over, and offerings range from the simple (mini-croissants and fromage lardons from Maison Villatte) to the elaborate (toasted brioche topped with pork-liver mousse, Champagne-vanilla aspic, malted-milk crumb, tarragon gelée, and pickled baby carrots from Tastings bistro). Crash at the family-owned Baileys by the Sea (from $215; baileysbythesea.com), and you’ll awake each morning to a locally sourced multicourse breakfast served on the house’s wraparound porch. On Sunday, walk off the food coma in historic Falmouth Village, or drive to Woods Hole and gaze at the Edward Hopper–evoking Nobska lighthouse.
If you stay:
Kanye West joins a much older, rounder Axl Rose for the Governors Ball Music Festival (June 7–9; governorsballmusicfestival.com) on Randalls Island. In Manhattan proper, the musically inclined can jam on the ivories of a John Varvatos–styled piano parked outside Alice Tully Hall; it’s one of 88 decorated uprights and baby grands dotting the five boroughs as part of the Sing for Hope Pianos project (pianos.singforhope.org). And June 6 to 9, find out why Rob Delaney is one of Twitter’s first breakout comedians when he takes the stage at Carolines on Broadway (carolines.com).
June 14-June 16
If you go:
Copake Lake, New York
2 hours by car
Copake Country Club’s eighteen-hole course is renowned for its heart-stopping views of the Berkshire foothills, and this Father’s Day, dads golf for free when accompanied by a paying son or daughter ($65 for adults, cart included; $15 for kids under 14; 44 Golf Course Rd.; 518-325-4338). No membership is required for a meal at the Greens (518-325-0019), the club’s locavore restaurant, which grows herbs and veggies in a garden by the fourteenth tee. For accommodations, consider Mount Merino Manor (from $225; mountmerinomanor.com), a hilltop Victorian B&B in nearby Hudson.
If you stay:
In a rare New York detour, D.C.’s Savor: An American Craft Beer & Food Experience (June 14–15; savorcraftbeer.com) swoops into the Metropolitan Pavilion. Also June 15: Lumen (lumenfest.org), a six-hour video-and-performance-art festival at Staten Island’s Lyons public pool.
June 21-June 23
If you go:
North Adams, Massachusetts
4 hours by car; 4.5 hours by bus
Commune with fellow Wilco lovers at the three-day Solid Sound Festival (from $65; solidsoundfestival.com), a family-friendly music extravaganza curated by and featuring the band, at the Massachusetts Museum of Contemporary Art (MassMoCA). Camp within a mile of the museum’s renovated nineteenth-century mill buildings ($90 per tent plot; $120 per RV plot) so you don’t miss a second of Yo La Tengo, Neko Case, White Denim, Low, and, of course, Wilco, who for the first (and probably last) time will play an all-request set on Friday. Also on deck: stand-up sets by John Hodgman and Reggie Watts and farm-to-table Berkshire eats at two new charity food events—local hors d’oeuvre and spirits ($90) and a midnight sit-down dinner with band members in the museum ($275).
If you stay:
On June 22, the Quiet Clubbing Pub Crawl (quietevents.com) puts a flash-mob spin on barhopping by pumping D.J. mixes into the wireless headsets of 100 hedonistic beatheads. The next day, the line between experimental art and music blurs as John Zorn premieres two warped vocal works alongside James Turrell’s rotunda-flooding light sculptures at the Guggenheim. And running all weekend is a kid-friendly immersive theater piece The Reptile Under the Flowers at St. Ann’s Warehouse (stannswarehouse.org). Think Sleep No More, only with puppets.
June 28-June 30
If you go:
Beach Haven, New Jersey
2 hours by car
Real-life drama unfolded at Long Beach Island’s 450-seat Surflight Theatre/Broadway on the Beach (201 Engleside Ave., Beach Haven; 609-492-9477) last October when Sandy water reached as far as row H. Four months later, the 63-year-old theater returned swinging with a full lineup of performances. George M!, running June 19 through July 7, features Drew B. James as wisecracking song-and-dance legend George M. Cohan, performing showstoppers like “Give My Regards to Broadway” and “Yankee Doodle Dandy.” Book tickets in advance ($45), along with a room at The Gables (from $250; gableslbi.com), an elegant Victorian inn that has made a comeback after the double whammy of a fire followed by Sandy flooding. For a pre-curtain dinner, lock in a table at beloved BYOB Mediterranean spot Carmen’s (122 North Bay Ave.; 609-848-9650).
If you stay
Bring a Scrabble board to the Museum of Mathematics (momath.org) on June 28 for one-on-one lessons with three-time national champ Joe Edley. Or catch a whole other kind of genius on display the following day, as BAM welcomes The Hitchcock 9 (6/29–7/3; bam.org), the British Film Institute’s touring festival of the director’s newly restored silent films. Saturday screenings include The Ring and Blackmail, both with live musical accompaniment. That Sunday, Pridefest (nycpride.org) marches down Fifth Avenue, led by grand marshals Edith Windsor, Harry Belafonte, and Earl Fowlkes.
JULY
July 4-July 7
If you go:
Providence, Rhode Island
3.5 hours by car
The Rhode Island School of Design Museum (224 Benefit St.; 401-454-6500) is one of the best small museums on the East Coast; and if you’re the type of guy whose bow tie matches his suspenders, it’d be a shame to miss RISD’s “Artist/Rebel/Dandy: Men of Fashion” exhibition (through August 18), covering everything from OG dandy Beau Brummell to the Sartorialist. Ogle one of Oscar Wilde’s button-downs, plus suits that belonged to Fred Astaire and John Waters. Chase the tour with a pickleback shot and dancing at the two-story Salon (57 Eddy St.; 401-865-6330), before passing out at the boutiquey Hotel Providence (from $219; hotelprovidence.com).
If you stay:
One of the standout parties in Verboten’s new StageONE concert series (residentadvisor.net) goes down on the Fourth, with D.J. Sasha dropping superclub sounds on the Williamsburg waterfront. On July 6, there’s a mock Miss America pageant starring Justin Vivian Bond at Fisher Center’s Spiegeltent (fishercenter.bard.edu).
July 12-July 14
If you go:
Bridgehampton, Long Island
2 hours by car; 3 hours by LIRR
For art, dumplings, and possible rock-legend sightings, head to the third annual artMRKT Hamptons (July 11–14; tickets from $20; art-mrkt.com/hamptons), a four-day fair held on the grounds of the Bridgehampton Historical Society. Hundreds of works by emerging and established artists from 40 galleries—including Chelsea’s Nancy Hoffman, Bushwick’s Fuchs Projects, and L.A.’s CB1—suit collectors both casual and less so, with prices ranging from $2,000 to $50,000. No bank? No problem. Go for the food and people-watching instead: Trucks from Red Hook Lobster Pound, Rickshaw Dumplings, Montaco, and Van Leeuwen Artisan Ice Cream are a vast improvement over the usual stuffy (or absent) gallery fare, and last year’s attendees included Jon Bon Jovi, Edie Falco, and erstwhile Housewife Dina Manzo. Check in to the conveniently located Sag Harbor Inn (from $429; sagharborinn.com), and round out the weekend with a taco lunch from La Fondita (74 Montauk Hwy.; 631-267-8800) and an afternoon of Rosato tasting at East End winery Channing Daughters ($10; 1927 Scuttlehole Rd.; 631-537-7224).
If you stay:
Join thousands of MLB obsessives at the Javits Center for the All-Star Fanfest (July 12–16; mlb.com), a veritable baseball theme park for snapping up memorabilia, testing new gear, and collecting eBay-gold autographs. On July 13, India’s Holi Festival meets an all-ages fun run when the Color Mob 5k (colormob5k.com) beats a path through the city; wear white, as you’ll be doused head-to-toe in neon-hued cornstarch. Later that night, head to the Prospect Park band shell for a free screening of Bela Lugosi’s Dracula (bricartsmedia.org), preceded by a musical set from singer-violinist Kishi Bashi.
July 19-July 21
If you go:
Chincoteague Island, Virginia
5 hours by car
In July—as those who grew up reading Marguerite Henry’s Misty of Chincoteague will recall—the wild ponies who live on the 37-mile barrier island of Assateague make their annual swim across the channel to Chincoteague. Starting this weekend, the town’s “saltwater cowboys” begin rounding up the horses for July 24’s pony swim. Hole up in Miss Molly’s Inn (from $165; missmollys-inn.com), the seven-room B&B where Henry wrote her famous children’s book in 1947. Make good use of the free bikes, beach chairs, and boogie boards as you spend Saturday relaxing on Assateague’s pristine white beaches (daily parking passes are $8) or cycling along its picturesque biking trails. Around 4:30 p.m., wander over to the south side of the island and watch as the cowboys lead the ponies to an enclosed pen. The corralling continues on Sunday at 8 a.m. on the north side, though seeing it involves a six-mile hike. Come nightfall, head to the Chincoteague Volunteer Fireman’s Carnival on Main Street for raffles, rides, and fried oysters aplenty.
If you stay:
Get a head start on the summer’s hottest concert—Jay-Z and Justin Timberlake at Yankee Stadium—aboard the pre-party Rocks Off booze cruise, setting sail at 5:30 p.m. on July 19 (rocksoff.com). The next morning, Nitehawk Cinema’s “Art Seen” series (nitehawkcinema.com) screens Beauty Is Embarrassing, a doc about multimedia visionary and Pee-wee’s Playhouse puppet designer Wayne White.
July 26-July 28
If you go:
Finger Lakes, New York
4 hours by car
Fifty-one weeks a year, the Finger Lakes region lures travelers with waterfall trails, peaceful retreats, and vineyard tours. But the last weekend of July, the towns around Cayuga Lake roll out a different kind of welcome mat: a patchwork of roadside blankets and front-porch displays piled high with antiques, farm tools, and sundry attic treasures. Now in its 25th year, the 50-Mile-Long Garage Sale (July 27–28; 800-499-9615) runs on State Route 90 between Homer and Montezuma, passing through seven tiny hamlets (and plenty of pastureland). Expect to find 300 to 500 vendors, with residents, businesses, and community groups all pitching in. Sale hours are 8 a.m. to 4 p.m., but the best time to shop is early morning (to avoid the crowds) or late Sunday (when prices plummet). Stop for lunch in storybook Aurora, where Pumpkin Hill Bistro (2051 Rte. 90; 315-364-7091) serves pan-seared local duck breast and charred, sugar-crusted salmon in 1820s farmhouse environs. Three miles up the road, Captain Skip Stamberger’s year-old Water to Wine Tours invites folks aboard a fifteen-passenger, 26-foot harbor launch boat for daily five-hour cruises with stops at three lakeside vintners ($85; watertowinetours.com)—a no-stress solution for anyone debating designated-driver duties. The best place to spend the night: Cortland’s timber-and-stone Hope Lake Lodge ($916 for two nights; hopelakelodge.com), with an on-site spa and indoor water park and easy access to the sale route’s starting point in Homer, ten miles north.
If you stay:
Hop the ferry to Governors Island to see 200 wordsmiths across three stages as part of the Poetry Society of New York’s two-day Poetry Festival (July 27–28; govisland.com). That Sunday, Kronos Quartet celebrates its 40th anniversary at the Damrosch Park band shell by playing the dizzying works of Dan Deacon, Amon Tobin, and the National’s Bryce Dessner (lcoutofdoors.org).
AUGUST
August 2-August 4
If you go:
Newport, Rhode Island
3 hours by car
Each summer, the three-day Newport Jazz Festival (August 2–4; tickets from $74; newportjazzfest.net) erects three stages overlooking Narragansett Bay. It’s here that well-heeled audience members will drop anchor and take in this year’s headlining acts (Natalie Cole, Chick Corea, Herbie Hancock) from aboard their yachts; for the rest of us, a simple picnic blanket on the grounds of Fort Adams State Park works just fine. Next to the alfresco jazz marathon, a new 430-foot zip line will debut in June, allowing users to traverse the fort from a height of 60 feet ($6; fortadams.org). Downtown, try the fresh lobster rolls ($19) at Lobster Bar (31 Bowens Wharf; 401-619-2890)—the bustling eatery is housed at the end of a pier inside Aquidneck Lobster Company, where orange-suited fishermen unload their catches daily. At night, settle into the Cliffside Inn (from $410; cliffsideinn.com), a fully restored 1876 mansion with Victorian-era décor, fireplaces in every room, and original artworks by onetime inhabitant Beatrice Turner. Accessible from the inn is Cliff Walk, a dramatic, 3.5-mile paved oceanfront walkway that meanders behind the Newport mansions—one of which (Rosecliff) was featured in the 1974 version of The Great Gatsby.
If you stay:
Look no further than the August 2–4 Bieber-Beyoncé takeover of Barclays Center (barclayscenter.com) for proof that the new arena is as serious about its concert programming as MSG. Also on August 4: TEDxUpperEastSide (tedxuppereastside.com) takes over the Bohemian Benevolent Society with its signature mix of cerebral speakers and performances.
August 9-August 11
If you go:
Brattleboro, Vermont
3.5 hours by car
A double feature at the Northfield Drive-In ($9.50; 981 Northfield Rd., Hinsdale; 603-239-4054), one of a handful still operating in New England, has the power to pull a person straight out of the muggy misery that is New York in August and into a far more idyllic version of summer. On Friday, check in to Forty Putney Road Bed and Breakfast (from $199; fortyputneyroad.com), a 1929 home built to resemble a French château. Grab one of the locally brewed beers at the inn’s pub before dinner at T.J. Buckey’s (132 Elliott St.; 802-257-4922), a sixteen-seat locavore restaurant in a vintage train dining car. The next day, pick up overstuffed barbecued-pork sandwiches ($5.25) at the Vermont Country Deli (436 Western Ave.; 802-257-9254) and drive to the relatively secluded Harriman Reservoir, about 30 minutes west of Brattleboro. Head back to town in the mid-afternoon—the drive-in opens at 6:30 p.m., and early arrival is essential for staking out a prized first-row spot. While waiting for the sun to go down, grab dinner at the snack bar, whose offerings put standard multiplex fare to shame (homemade spinach pie, spring rolls, and popcorn with real butter). As for the movies, they tend toward first-run family-friendly films, and the second one wraps up by 1 a.m.
If you stay:
Party promoters Gemini & Scorpio make their tenth anniversary count by bringing San Francisco’s punky underground circus Vau de Vire Society and rogue orchestra Hungry March Band to Lincoln Center’s Out of Doors fest (August 9; lcoutofdoors.org). On August 10, the Museum of Modern Art unveils “Soundings: A Contemporary Score,” its first in-depth examination of sound art, with works by sixteen international artists (through November 3; moma.org). Then on Sunday, the D.J. Kool Herc–headlined tribute “Back to the Roots” lionizes 40 years of hip-hop at one of its most iconic (and endangered) hubs, the 5Pointz Aerosol Art Center in Long Island City (5ptz.com).
August 16-August 18
If you go:
New Paltz, New York
1.5 hours by car
Even the most seasoned barbecuers can learn a trick or two at the Hudson Valley Ribfest (August 16–18; hudsonvalleyribfest.org), now in its ninth year. The three-day pig-out, held at the Ulster County Fairgrounds, kicks off at 5 p.m. Friday with a multi-vendor rib dinner and country music. Over the weekend, more than 50 teams will compete for champion titles. Eat yourself silly sampling the regional offerings (the $5 daily admission includes parking but no food) or wander around the contest area and grill competitors about their cooking setups and secret sauces. When you’re ready to give your belly a rest, take a dip in the Split Rock swimming hole at the 8,000-acre Mohonk Preserve (mohonkpreserve.org), hike one of its many trails, and then shower up at the 1850 House Inn & Tavern (from $249; the1850house.com), a boutique hotel in a historic brick building with views of Rondout Creek.
If you stay
From 7 a.m. to 1 p.m. on August 17, Mayor Bloomberg’s Summer Streets Initiative (nyc.gov/summerstreets) shuts down Park Avenue from Central Park to the Brooklyn Bridge; BYO bike, skateboard, or running shoes. That night, SummerStage puts on Randy Weiner and Alfred Preisser’s hip-hop remake of King Kong in Marcus Garvey Park (cityparksfoundation.org); their version, set in the South Bronx in the seventies, stars a rhyme-dropping emcee.
August 23-August 25
If you go:
Greenport, Long Island
2 hours by car; 3 hours by LIRR
When cycling to Coney no longer satisfies, head to the North Fork, where traffic is light and the hills are few. The North Fork Century Ride ($100; northforkcentury.com) makes the trip easy, mapping back-road routes of 25, 50, 72, or 100 miles. Each passes a lavender farm and untamed fields on the way to Orient Point; longer routes hit the fork’s southern shore. The fee buys you roadside support, showers, and spirited riding buddies—plus rest stops piled with snacks. Organizers can arrange day-of transportation, but consider overnighting at the retro Silver Sands Motel (from $150; silversands-motel.com) and visiting a winery like Coffee Pot Cellars (31855 Main Rd., Cutchogue; 631-765-8929), which just opened a tasting room.
If you stay:
Tinted SUVs descend on Barclays Center August 25, as MTV presents its 30th annual Video Music Awards. Can’t swing tickets? See wannabe fameballs at a free screening of Fame, part of “Movie Night” at Fort Greene’s Habana Outpost (habanaoutpost.com).
August 30-September 2
If you go:
Baltimore, Maryland
2.5 hours by Amtrak; 3.5 hours by car
The three-day Grand Prix of Baltimore (from $5; grandprixofbaltimore.com) roars into Charm City, featuring 180-mile-per-hour races along a two-mile harborside track. Between bouts, sample Maryland craft beers ($6–$9) and dig into tomato ravioli in local blue-crab vinaigrette ($18) at newcomer Birroteca (1520 Clipper Rd.; 443-708-1934), located inside a restored historic mill. Then visit the new “Blacktip Reef” exhibit at the National Aquarium (from $21.95; 501 E. Pratt St.; aqua.org) for a look at an endangered-coral ecosystem inhabited by sharks, stingrays, and a 400-pound sea turtle. Also new this summer is the Urban Beach Bash Series (waterfrontpartnership.org): free D.J.-ed parties, with booze and food trucks, most Sundays in West Shore Park. Book ahead to secure a room at the conveniently located Fairfield Inn & Suites in the Inner Harbor (from $159; greenfairfieldinn.com).
If you stay:
One last hurrah before summer slips away: Electric Zoo (August 30–September 1; electriczoofestival.com) fêtes its fifth anniversary with five stages of woofer-wrecking dance music from David Guetta, Steve Aoki, and others. This weekend also marks the penultimate chance to see the International Center of Photography’s triennial, “A Different Kind of Order,” featuring works by 28 film and video artists (through September 8; icp.org). Of course, there’s always next summer—which in this case means 2016.
Reporting by Joshua M. Bernstein, Julie Besonen, Rebecca Dalzell, Alyssa Giacobbe, Molly Langmuir, Jenny Miller, Andrew Parks, Valerie Rains, Alex Schechter, Celia Shatzman, Alexis Swerdloff, Alexa Tsoulis-Reay, and Erin Wylie.