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:
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:
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.