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)

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)

New York Renaissance Faire 

Weekends from Aug 5 – Oct 1
Celebrating its 40th season in 2017, this eight-week event is a rollicking re-creation of Elizabethan times, complete with re-enactments of Robin Hood’s escapades, a human chessboard, and person-powered carousel. (Saturdays, Sundays and Labor Day, 600 Rte 17A, Tuxedo Park; www.renfair.com/ny)

Putnam County Wine and Food Fest 

Aug 12 – 13
Quaff vinos from around the state while you feast on savories and listen to live music. Bring the whole family, along with lawn chairs and blankets. (Iron & Wine Restaurant and Westview Golf Driving Range, 3191 Rt 22, Patterson; 800.557.4185, ext. 3; www.putnamcountywinefest.com)

Sangria Festival 

Aug 12
Get your fruit on by sampling not the same old sangria. Caterers and food trucks are also on hand, and get a henna tattoo or have your tarot cards read while you’re at it. (Hudson-Chatham Winery, 1900 Rt 66, Ghent, 518.392.WINE; www.hudsonchathamwinery.com)

Hudson Valley Magazine’s Burger & Beer Bash

Aug 17
Eat, drink, dance, and vote on your favorite burger at our fifth annual summer event. Chefs feature all types of burgers (not just beef) and plenty of sides and desserts!  (Dutchess Stadium, 1500 NY-9D, Wappingers Falls; www.hvmag.com/burgerbash)

Hudson Valley Ribfest 

Aug 18 – 20
This official New York State Championship barbecue contest offers more than just meat: there’s live music, cooking demonstrations, and plenty of other food choices. (Ulster County Fairgrounds, 844.RIBFEST; www.hudsonvalleyribfest.org)

Dutchess County Fair

Aug 22 – 27
This fair comprises 162 acres of agricultural and horticultural displays, animal and food competitions, a concert series, rides, and those famous milkshakes at the 4-H booth. (Dutchess County Fairgrounds, 6550 Springbrook Ave [Route 9], Rhinebeck; 845.876.4000; www.dutchessfair.com).

Hudson Valley Hoot  

Aug 25 – 27
Square dancing, fiddlers, storytelling, and late-night jam sessions are just some of the old-fashioned fun to be had at this three-day, multi-stage fest. (The Ashokan Center, 477 Beaverkill Rd, Olivebridge; 914.466.8334; www.homeofthehoot.com)

September

Woodstock/New Paltz Art & Craft Fairs 

Sept 2 – 4
This 35-year-old event draws more than 10,000 visitors and features 300 juried artists and craftspeople. (Ulster County Fairgrounds, 249 Libertyville Rd, New Paltz; www.quailhollow.com)

Hudson Valley Wine and Food Festival 

Sept 9 – 10
Sample wines from more than 60 New York State wineries, not to mention craft beer, spirits, and hard ciders. (Dutchess County Fairgrounds, 6550 Springbrook Ave [Route 9], Rhinebeck; 845.658.7181; www.hudsonvalleywinefest.com)