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

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

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. Plus, with the warm weather in full swing in the region, there’s no better way to celebrate the arrival of summer than 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

Capital Strawberry & Wine Festival

Altamont Fairgrounds, Altamont
June 3-4, 10 a.m. – 5 p.m.

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This berries-and-booze bash in Albany is the perfect way for foodies to spend their first weekend of June. The festival will feature strawberry desserts, cocktails, and wine, and the tasting room will dole out New York wine, spirits, mead, and cider. Additionally, the event will have food trucks, live music, and activities for children.

Pinkster Celebration

Schuyler Mansion State Historic Site, Albany
June 3, 11 a.m. – 4 p.m.

Congregate with family and friends at this festival comprising storytelling, drumming, dance, historic performances, and craft and food vendors. The tradition—at one time a Dutch holiday commemorating Pentecost—evolved into a spring festival which celebrates culture brought to the Hudson River by West and Central Africans who were enslaved.

Summer Solstice Stroll

Albany Pine Bush Preserve, Albany
June 21, 1 p.m.

Observe the summer solstice—the longest day of the year—at the Albany Pine Bush Preserve with a two-and-a-half mile walk into the Karner Barrens region of the preserve. Visitors will “enjoy the mid-day sun, observe how the shadows move, and listen for the sounds of summer.” The walk commences at trailhead #1, and there is a suggested donation of $5 for this event.

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Columbia County

Pride Festival

Warren Street, Hudson 
June 1-4 

June is a historic month for the LGBTQ+ community, and the city of Hudson will celebrate the queer community with its 14th annual pride festival. Be sure to check out the events happening all weekend long, from the rainbow flag raising ceremony to various drag performances.

The Resistance Revival Chorus

Promenade Hill Park, Hudson
June 17, 7:30-9:30 p.m. 

Have an appreciation for music and social justice issues? Come watch The Resistance Revival Chorus (RRC) showcase the magic music can create in building a space for women and non-binary artists to share their stories. The outdoor concert is free for all.

42nd Street

Mac-Haydn Theatre, Chatham
June 22 – July 2

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The Tony Award-winning musical 42nd Street returns to the Mac-Haydn Theatre and will surely be an unforgettable show. The musical follows aspiring chorus singer Peggy Sawyer and the struggles she faces on Broadway during the Great Depression. With its mesmerizing tap dancing and offbeat characters, the performance will make you feel like you are right on Broadway. Tickets are $48.50.

Dutchess County 

Kaatsbaan Spring Festival

Kaatsbaan, Tivoli
June 2-18 

Nestled away in the quaint village of Tivoli, Kaatsbaan is a hub for all things art. Over the course of this spring festival, attendees can enjoy art in many forms, from sculpture to music to dance. Stop by to get inspired by the incredible artistry of the Limón Dance Company, GRAMMY-nominated violinist and composer Curtis J. Stewart, and more.

Bard SummerScape

Bard College, Annandale-on-Hudson 
June 22 – August 13

This two-month festival at Bard College will immerse you in the world of some of the Hudson Valley’s top musicians and performers. Celebrate the 20th anniversary of the Fisher Center with a showing of Henri VIII or Illinois. For something a little more upbeat, be sure to check out the Spiegeltent on the weekends for live performances and more.

PKGO Pride Parade and Festival

Waryas Park, Poughkeepsie 
June 10

An inclusive and fun-filled event for all, Poughkeepsie’s annual pride parade and festival hosted by the Dutchess County Pride Center is a hit every year. With local queer-owned businesses, food stalls, and a variety of activities, the Queen City of the Hudson will shine with a vibrancy of celebration and love. The parade begins at noon at the intersection of Main St. and Market St.

Orange County

Bike and Brew

Rushing Duck Brewing, Chester
June 3, 1-5 p.m.

It’s exactly what it sounds like: beer, bikes, and cider! Start at Rushing Duck in Chester, then bike on the Heritage Trail—which is flat and paved—for 18 miles to Soons Orchard for cider and snacks. The $30 event charge includes beer and cider on each end of the ride.

Warwick Pride

Warwick Valley Community Center, Warwick
June 11, 11 a.m.

The festivities for Warwick Pride kick off at the community center, where attendees will eat brunch, listen to music, and socialize. At 1:30 p.m., the parade will step off, led by the Funkrust Brass Band, towards Main Street. The parade concludes at Stanley Deming Park with a drag show hosted by Ms. Eve Starr from 2:30-4:30 p.m. The event is free to attend, and all are welcome.

Father’s Day Car Show

Devitt’s Nursery & Supply, New Windsor
June 17, 10 a.m. – 2 p.m.

Autophile fathers will love celebrating Father’s Day (one day early) at this car show, complete with grilled grub; live music by The Good, The Bad and The Ugly Band; and all the cars, trucks, and motorcycles you could ask for. Trophies will be awarded for “Best in Show,” so if Dad has a machine of his own, take advantage of the free entry to the competition.

Putnam County

Henry V

Hudson Valley Shakespeare Festival, Garrison
Friday – Sunday, 7:30 p.m. through August 21

Once more unto the breach, dear friends, once more! To kick off the summer season at the Hudson Valley Shakespeare Festival, audiences will watch as Shakespeare’s warrior-prince mounts his crusade for the French crown. This classic gets a twist in the way of casting, as the role of Henry will be performed by Emily Ota.

Wright Over Water

The Massaro House, Lake Mahopac
Tuesdays and Wednesdays, June 6-21

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Take a tour of this masterpiece by the late architectural great, Frank Lloyd Wright, on Lake Mahopac’s Petre Island. Guided by a member of the Massaro family, visitors will have the opportunity to peek inside the house and guest cottage. Tours cost $150 per person—including the boat ride—and children 12 and older are welcome.

Putnam Pride

Old Town Hall, Brewster
June 24, 1 p.m.

March from the old town hall to Wells Park at Putnam County’s celebration of pride. Paradegoers can listen to speakers, shop from local vendors, and listen to live music by Angel Elektra and Shay D’Pines! There is limited accessible parking at Wells Park and parking for the general public at the Metro-North train station.

Rockland County

First Annual Strawberry Festival

Rockland Farm Alliance, New City
June 10, 10 a.m.

Celebrate the first year of strawberry picking at Rockland Farm Alliance with this berry-centric festival. There will be games for children, food trucks, vendors, and more. We can confidently say it will be a berry good time.

First Annual Piermont Festival of Hudson Valley Arts

Downtown Piermont
June 10, 12-8 p.m.

Piermont is known as one of the artsiest little villages in Rockland County, and that’ll be on full display at the first Festival of Hudson Valley Arts. Piermont’s downtown area will be overtaken with live performances, art exhibitions, artisan markets, music, and more. Be sure to take a walk on the pier while you’re in town for exceptional views of the Hudson River.

Eighth Annual Juneteenth Celebration Weekend

Haverstraw African American Memorial Park, Haverstraw
June 16-18

Commemorate Juneteenth at this weekend of celebration with the Haverstraw African American Connection. On Friday at 5:30 p.m., there will be a flag raising ceremony and dancing under the stars; on Saturday from 3-6 p.m., attendees can enjoy activities, food, and the musical stylings of Anointed Friends in Haverstraw African-American Memorial Park; and on Sunday from 1-3 p.m., the weekend will conclude with gospel in the park.

Ulster County

Queer Summer Nights: Orchard Disco

Bad Seed Cider Taproom, Highland
June 10, 6-10 p.m.

Dancing under the stars? Pizza and snacks? Locally brewed cider? Pinch us, we might be dreaming of our ideal Saturday night. No, this Orchard Disco at Bad Seed is 100 percent reality, and here’s the kicker: It’s free to attend, and dogs are welcome.

Reggae on the Rock: Mystic Bowie’s Talking Dreads

Opus 40, Saugerties
June 17, 6-8:30 p.m.

Reggae on the Rock is exactly what it sounds like: great music performed at Opus 40, the sculpture park completed by one man, Harvey Fite, over the course of four-or-so decades. In addition to the tunes, attendees can look forward to Jamaican food a la Hellshire Cuisine of Poughkeepsie, burgers by Kingston’s Meat Things, and beverages courtesy of Stockade Tavern. Tickets run $25.

St. Augustine’s Food Truck Bazaar

St. Augustine School, Highland
June 22-25

If amusement rides, food trucks, samples from local restaurants, live music, and raffles sounds like your idea of a good time, spend a day at the St. Augustine’s Food Truck Bazaar and fill yourself with all the fun and food you can muster. The event is free for all to attend.

Westchester County

Yonkers Waterfront Live

71 Water Grant Street, Yonkers
Fridays through August 25, 6:30-8 p.m.

Nothing to do on a Friday night? Well, you can rest assured that there will be live music, dancing, and fun to be had on the waterfront in Yonkers. Every Friday through August 25, musicians will take to the stage with salsa, jazz, disco, blues, and soul—a little something for everyone.

Westchester Magazine’s Wine & Food Festival

Various locations in Westchester County
June 6-10

If you attend just one food festival in Westchester this summer, it should be Westchester Magazine’s Wine & Food Festival. We might be a little biased, but after all, where else can you enjoy such a rich array of wine, beer, and food? Attendees can meet local chefs, savor tastings, view cooking exhibitions, and so much more.

Yonkers Pride Festival

Downtown Yonkers
June 10, 2-8 p.m.

Whether it rains or shines, head down to downtown Yonkers for the sixth annual pride parade. The event is complete with drag performances, food and craft vendors, games, activities, and plenty of pride to go around.

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