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An Insider’s Guide to July Events in the Hudson Valley

Photo by Alanna Floreck

Hudson River tourism directors share their top picks for places to go, sights to see, and things to do throughout the month of July.

By Emma Denes, Savannah Messam, and Matt Moment

We’ve said it before and we’ll say it again. There are a ton of things to do in the Hudson Valley each month, with dozens of ways to experience the best of what the region has to offer. Whether your idea of a good time is getting active outdoors, jamming out to live music, or chilling out with a glass of local vino, the Hudson Valley is the place to spend the warm months. Celebrate the arrival of summer with outdoor events and visits to scenic, open-air destinations.

To help scout out the hottest events in the Valley, we reached out to local tourism directors from Albany to Westchester for their top picks for things to do. Check out their selections, then get planning!

Albany County

Head Over Heels

Washington Park, Albany
Thursdays, June 30 – July 23, 8 p.m.

We’ve all seen Wicked, Phantom of the Opera, and Kinky Boots, but how often do you get to see a new musical? Head Over Heels is a new musical comedy that features the iconic hits of The Go-Go’s and Belinda Carlisle. Whether you love “We’ve Got the Beat” or “Heaven Is a Place on Earth” or one of the other 20 ‘80s hits, you’ll be sure to tap your toes and bust a gut. Come and see for yourself why this “isn’t your average jukebox musical.”

Alive at Five Music Festival

Jennings Landing, Albany
Various dates throughout the summer


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Since the summer of 1990, the Capital Region has rocked out at this free concert series. This year, attendees can look forward to performances by the likes of Talib Kweli, State Champs, and Doug E. Fresh. Spanning eight weeks in total, the festival aims to cater to all musical tastes and feature big names alongside up-and-comers. What better way to unwind after work than with live music in the park?

Columbia County

Chatham SummerFest

Main Street, Chatham
July 9, 11 a.m. – 4 p.m.


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Kick off the summer season with food, entertainment, and vendors at the annual Chatham SummerFest. Stop by one of six food trucks to satisfy your cravings, from mac and cheese to ice cream. Catch a live screening of the documentary “The Biggest Little Farm,” or laugh along with Bruce Bowey’s Zany Family Fun Show. And, of course, make sure you don’t miss the Main Street Parade at 1:30 p.m.

The Blueberry Festival

State Route 22, Austerlitz
July 31, 9 a.m. – 3 p.m.

Besides blueberry pies, blueberry bushes, and blueberry pancakes, this annual festival will host a variety of activities for the whole family to enjoy. From a tag sale and animal exhibits to pottery demonstrations and magic acts, there will be a little something for everyone. Admission fees go towards the Austerlitz Historical Society.

Dutchess County

Powerhouse Theater 

Vassar College
June 26 – July 21 

A collaboration between Vassar and New York Stage and Film, Powerhouse Theater is where great plays and musicals are born. This season, catch musical workshops of Luna and the Starbodies and Shakespeare: Unplugged, as well as play workshops of The World Is Not Silent, Sweet Chariot, and Tell Them I’m Still Young. And don’t miss additional productions of play readings and free performances from the training company.

Upstate Art Weekend

Multiple locations
July 22 – 24

Art fans, rejoice—the third annual UPAW is back and better than ever with more than 145 participants displaying projects, exhibits, and studios. Event visitors can utilize the interactive Google map to take a self-guided tour of some of the best artistic creations upstate New York has to offer. Aside from Dutchess, feel free to travel to other counties in the Hudson Valley to get a taste for creativity throughout the region.

Pride in July

Apple Tree Lane, Poughquag
July 24, 2 – 10 p.m.


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Just because Pride Month is over doesn’t mean that Dutchess is done celebrating! So is the spirit at Barton Orchards, where a rainbow of excitement is awaiting all attendees. On top of a farmers’ market, animal zoo, and gemstone mining, Tina Burner of “RuPaul’s Drag Race” will make a special appearance alongside New England drag queens Summer Orlando and Barbra Streetsand.

Greene County

Summer Concert Series

The Grazhda Music and Art Center, Jewett
July 1 – September 4

Get a taste of Ukrainian culture with this summer concert series in the Catskills. Established in 1983 by Dr. Ihor Sonevytsk, a Ukrainian-born composer and musicologist, the Music and Art Center has hosted prolific artists such as Metropolitan Opera bass Paul Plishka, pianist Alexander Slobodyanik, composer Miyroslav Skoryk, and Kyiv Opera tenor Anatoliy Solovyaneko. Also be sure to stop by the St. John the Baptist Ukrainian Catholic Church—the architecture alone is alluring, and this summer, it will host an art exhibit featuring Ukrainian artists with ties to the Hunter area.

Orange County

Warwick Food Truck Festival

St. Stephen’s Place, Warwick
July 7, 4–9 p.m.

Get your groove on and nosh on good eats at the annual Warwick Food Truck Festival, where one can indulge in a whole slew of culinary delights. The festival offers a little something for everyone including birria tacos, sandwiches, cream puffs, barbecue favorites, egg rolls, and dumplings stuffed with unusual, yet mouthwatering fillings. Cleanse your palate with a craft brew from Rushing Duck Co., Pennings Farm Cidery, Parked Prosecco, and more. Before you slip into a food coma, enjoy live music by The Barrelhouse Blues Band and Missy and the Cat in the Hat.

The Beatles Festival

Palaia Winery and Meadery, Highland Mills
July 31, 12–10 p.m.

Find reprieve from a “Hard Day’s Night” at this festival of music at Palaia Winery. The all-day event features live music from tribute acts such as Jim & Michelle Ianucci, British Legends of Rock Tribute Band, Bruce Perone, and the “Live, The Beatles” tribute band in costume. Food and beverage vendors will be available onsite and, while general admission is $10, children under 12 will be admitted free of charge.

Putnam County

Country Festival & 4-H Showcase

Veterans Memorial Park, Carmel
July 15, 6 p.m. – July 17, 11 p.m.

Who’s ready to get their twang on? At this three-day festival, attendees can look forward to food trucks, sweet treats, country-themed vendors, games, and family-friendly exhibits. Equestrians will love the horse showmanship demonstration, while little ones will enjoy the inflatables and the magic show. On Friday and Saturday night, there will be concerts under the stars, followed by a classic car show on Sunday.

Hudson Valley Shakespeare Festival

Season begins July 15
HVSF Theater Tent, Garrison

If you want to see great theater in New York, you needn’t head to midtown. Instead, see even more for less at Hudson Valley Shakespeare Festival, now at a new location in Garrison. This season, HVSF tackles a robust set of material, from Shakespeare’s Romeo and Juliet to Where We Belong by Madeline Sayet, a new playwright from New England. Tickets are on sale now—check out the website for a comprehensive list of this summer’s programming.

Hops on Hudson Modern Maker’s Market

Mayor’s Park, Cold Spring
July 16, 2–6 p.m.


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Over 50 makers of all mediums will take to Mayor’s Park with local beers and wines, food, handmade goods, artwork, and more. Don’t have a ride? No problem—the event takes place just a stone’s throw from the Metro-North Cold Spring train station. Once you’ve had your fill of the market, take a walk into the town of Cold Spring and enjoy the array of small businesses and family-owned restaurants.

Rockland County

Bastille Day in Piermont

Piermont Avenue, Piermont
July 16, 12–9 p.m.


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If you’re after a way to mark France’s national holiday, look no further than Piermont’s annual Bastille Day celebration. As you walk past all the French flags and enjoy live music, stop by restaurants, local shops, and art exhibits to remind yourself that truly, la vie est belle. And be sure to catch the reenactment of the Storming of the Bastille, as well as the guillotine replica (with a wooden blade, of course).

Ulster County

Taste History Aboard Solaris

Rondout Landing, Kingston
Every Friday, 7:30–8:45 p.m.

Join food historian Sarah Wassberg Johnson aboard Solaris for an informal chat as you sample bites and wine. With a resume including features on the History Channel mini-series The Food That Built America as well as pieces by NPR, the Atlantic, CNN, Johnson is the perfect guide for this foodie experience. Sit back, relax, and enjoy the ride as beautiful Hudson River views pass by.

Masters of the Telecaster

Bearsville Theater, Woodstock
July 15, 8–11 p.m.


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Two of the world’s leading guitarists—Jim Weider of The Band and the Levon Helm Band; G.E. Smith of Hall & Oats, Bob Dylan, and the SNL band—will take the stage to perform repertoire from Roy Buchanan, Little Richard, Neil Young, Jimmy Reed, Steve Winwood, Sam Cooke, and more. Whether you come for the musicians or the music they’re playing, it’s sure to be an incredible retrospective on the very best of rock and roll.

Safe Home

Shadowland Stages, Ellenville
July 15 – August 7


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First and foremost, we should note the playwrights of Safe Home: James Glossman and Tom Hanks. Yes, that Tom Hanks, the one you know and love from such films as Forrest Gump and Saving Private Ryan. The actor, producer, and director turned writer worked with Glossman to pen this story about Bert Allenberry, a “smart man, many say a genius.” He has everything—money, notoriety, success—except for time. The play follows his “time-bending odyssey” to find his way back home.

Westchester County

Tour of Kykuit, The Rockefeller Estate

The Rockefeller Estate, Sleepy Hollow
Saturdays and Sundays

For four generations, this estate was home to the Rockefeller family, which began with the philanthropist John D. Rockefeller, founder of Standard Oil, once the richest man in America. Now, his home is a historic site of the National Trust for Historic Preservation and is open to the public for tours. With three tiers of tours ranging from $18 to $60 per ticket, this is a great way to spend your weekend in the Hudson Valley.

Pleasantville Music Festival

Parkway Field, Pleasantville
July 9

Are you ready to discover your new favorite artist? Then come on down to the Pleasantville Music Festival, where all day long you can dance and sing to artists like X Ambassadors, Paula Cole, Black Joe Lewis, and more. The festival has even created a Spotify playlist with the performers in the lineup in case you’d like a taste of what to expect.

Jazz Festival

Caramoor, Katonah
July 30, 1 p.m.


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Westchester is where it’s at when it comes to music. After the Pleasantville Music Festival passes, you can look forward to an afternoon of jazz at Caramoor. Presented in collaboration with Jazz at Lincoln Center, the lineup will include modern-day jazz giants like Camille Thurman, the George Coleman Quartet, and the Chick Corea Afro-Caribbean Experience. For the daytime performances, Caramoor recommends you bring you own seating; the headliner, however, will perform at the Venetian Theater.

Related: 18 Hudson Valley Trails That Are Perfect for Summer Hikes