June
Powerhouse Theater

June – July
The Powerhouse Season brings fully produced plays, musical workshops, and readings of works-in-progress to Vassar College. The Humans, the musical Bright Star, and Hamilton got their start here. (Vassar College, 124 Raymond Ave, Poughkeepsie; 845.437.5907; www.powerhouse.vassar.edu)

Country Living Fair

June 2 – 4
More than 200 vendors from 25 states draw throngs to this annual gathering of antiques, crafts, art, upcycled and handcrafted goods. (Dutchess County Fairgrounds, 6550 Springbrook Ave

[Route 9], Rhinebeck; 866.500.3247; www.countryliving.com/country-living-fair)

Westchester Magazine’s Wine & Food Festival

June 6 – 11
On the menu this year is a Wine Tour of Italy at the Italian Cultural Center in Tuckahoe; the Beer & Burger Blast and Grand Tasting Village at Kensico Dam Plaza in Valhalla, and An Evening with Westchester’s Tastemakers at the Ritz-Carlton in White Plains. (www.westchestermagazine.com/winefood)

Hudson Valley Shakespeare Festival

June 8 – Sept 4
Come picnic on the lawn at Boscobel, then head into the tent for performances of the Bard’s best and other plays. In 2017: Twelfth Night, The Book of Will, Pride and Prejudice, The General from America, and Love’s Labour’s Lost. (Boscobel, 1601 Route 9D, Garrison; 845.265.9575; www.hvshakespeare.org)

Taste of Country

June 9 – 11
Grab your cowboy boots and head to Hunter for this three-day party. The 2017 event showcases Jason Aldean, Miranda Lambert, and Sam Hunt. Hop on the Sky Ride for a bird’s-eye view of the crowd. (64 Klein Ave, Hunter Mountain, Hunter; www.tasteofcountryfestival.com)

Mountain Jam

June 16 – 18
Hipsters and hippies alike flock to this three-day camping music fest featuring some 40 bands on multiple stages. Tom Petty and the Heartbreakers, the Steve Miller Band, and Peter Frampton are headlining. (64 Klein Ave, Hunter Mountain, Hunter; 855.821.9209, www.mountainjam.com)

Kfest

June 17
The popular music concert moves this year to the Bethel Woods Center for the Arts. Stars include Jason Derulo, Sean Paul, Jon Bellion, Austin Mahone, Tinashe, Dua Lipa, Clean Bandit, Matoma, The Vamps, Aaron Carter and Kyle. (Bethel Woods Center for the Arts, 200 Hurd Rd, Bethel; www.bethelwoodscenter.org)

Caramoor Summer Music Festival

June 17 – July 30
Bring your own picnic (or preorder one) and lay a blanket on the grounds of this estate to experience headliners including Grammy nominees Rhiannon Giddens and Sarah Jarosz and country legend Emmylou Harris. (June 17 through July 30; 149 Girdle Ridge Rd, Katonah; 914.232.5035; www.caramoor.org)

Photo by Gabe Palacio
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Clearwater’s Great Hudson River Revival

June 17 – 18
Seven stages of live music are set up at Croton Point Park, along with environmental exhibits, food, dance, and more. This year includes Arlo Guthrie, Joan Osborne, and Los Lobos. For more turn to page 26. (Croton Point Park, Croton-on-Hudson, www.clearwaterfestival.org)

July
A Gathering at Bethel Woods: Celebrating Peace, Love & Music

July 1
This gathering at the site of the original Woodstock festival kicks off at 3 p.m., and will include live music and activities for the whole family, plus a fireworks display at dusk. Rain date is July 2. (Bethel Woods Center for the Arts, 200 Hurd Rd, Bethel; www.bethelwoodscenter.org)

Stormville Airport Antique Show & Flea Market

Starting July 1 – 2
Six times per year, more than 600 vendors from eight states converge here. (July 1-2, Sept 2-3, Oct 7-8, Nov 4-5; 428 Route 216, Stormville; 845.221.6561; www.stormvilleairportfleamarket.com)

Hudson Valley Hot-Air Balloon Festival

July 7 – 9
Featuring 100 balloon launches, this weekend includes a petting zoo, hay rides, and fireworks. (July 7–9; Barton Orchards, 63 Apple Tree Lane, Poughquag; 845.454.1700; www.dcrcoc.org/balloonfestival)

Our Lady of the Resurrection Monastery Vinegar Festival

July 15 – 16
Restaurateurs and foodies pucker up for this two-day fest featuring organic, artisanal vinegars from the cellars of this rural monastery. (Our Lady of the Resurrection Monastery, 246 Barmore Rd, Lagrangeville; www.ourladyoftheresurrectionmonastery.webs.com)

Orange County Fair

July 20 – 31
Motocross racing, a demolition derby, an indoor safari, antique fire truck show, rides, and food make this a memorable time. (Orange County Fairgrounds, Carpenter Ave, Middletown; 845.343.4826; www.orangecountyfair.com)

Putnam County 4-H Fair

July 28 – 30
A three-day weekend of fun, this true country fair features animals, an auction, and master gardener plant sale. (Putnam Veterans Memorial Park, 201 Gipsy Trail Rd, Carmel; 845.278.6738; www.putnam.cce.cornell.edu/putnam-county-fair)

August
Ulster County Fair

Aug 1 – 6
People love this fair for the horse shows, Country Showdown music event, and the fact that one wristband takes you on all the rides. (Ulster County Fairgrounds, 249 Libertyville Rd, New Paltz; 845.255.1380; www.ulstercountyfair.com)