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

Adobe Stock / Olga Mishyna

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

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. The month of May is especially joyous, with all the nature in our area coming into colorful bloom. For those looking for an adventure, there is plenty to do outdoors—especially if gallivanting in a meadow of tulips is your idea of a good time. For those more interested in indoor activities, you can look forward to live music, world-class art exhibitions, and more.

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

Albany History Fair

Historic Cherry Hill, Albany
May 1, 12 – 5 p.m.

The fair returns in-person under the theme of “Albany and the Gilded Age.” Attendees can expect a fun and educational experience, complete with scholar talks, special tours, costume installations, period music by Friends Union, hands-on activities on “Getting Dressed in the Gilded Age,” games and family activities, vendors, and a teaser performance of one scene from Swept Clean, an original play by Krysta Dennis set at Cherry Hill in 1884.

Albany Tulip Festival

Washington Park, Albany
May 7-8


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In its 74th year, the tulip festival remains the signature spring event in Albany. Did you know there are over 150 varieties of tulips? They are all on view at this spectacular celebration of flora. Washington Park will appear transformed into a sea of over 140,000 tulips as the city celebrates its rich Dutch heritage, featuring artisans, a fine arts show, live music, and much more.

Lupine Fest

Albany Pine Bush Preserve, Albany
May 21


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Who knew that Albany was such a hub of efflorescence? Locals are invited to “celebrate the magic of spring” with fields of violet lupine flowers and Karner blue butterflies. This festival gives attendees a chance to see for themselves the beauty of this preserve as they take nature walks, engage in hands-on activities, and enjoy games, music, food, and so much more.

Columbia County

Last Train to Nibroc

Ghent Playhouse, Ghent
May 20–22, 27–29

The story begins in the winter of 1940 on a train headed east. A young serviceman—recently discharged—finds himself chatting up a young woman from Kentucky. She decides to share her seat with him, and the two find themselves kindling a mutual attraction that may just change their lives forever. Tickets range from $12-28 and are available online.

The Legend of The Waitress and the Robber

Performance Spaces for the 21st Century, Chatham
May 20 – 21

Performers at work on the production of The Legend of The Waitress and the Robber at PS21. Photo courtesy of Columbia County Tourism

The lyrics to the opening song of The Legend of The Waitress and the Robber aptly set the stage: “Imagine if you will, there’s a world much like ours. Maybe in the future. Or maybe even now. A world where every human lives separate and alone. The only interaction allowed – is on a phone.” This piece, written two years before anyone had even heard of the coronavirus, becomes even more relevant in an atmosphere succeeding social distancing and pandemic isolation. In an epic, dystopian musical, the players of PS21 examine the themes of family, ownership, and justice. Tickets range from $10-30 and are available online.

Lawn Game Olympics

Copake Country Club, Craryville
May 30, 12 p.m.

This Memorial Day, head over to the Copake Country Club for a sunny day of fun and games like cornhole, giant Jenga, and Kan Jam. Grab a drink and compete with a friend—if you’ve got serious lawn game skills, you might even win a prize! Open play will begin at noon, and the tournament will begin at 1 p.m. After the competition, open play will resume in tandem with a barbecue.

Dutchess County

Boat Ride to Bannerman Island

Long Dock at Beacon Point Park, Beacon
May – October


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All aboard! Take a ride on the Estuary Steward tour boat to Bannerman Island and visit the famous castle ruins, once a military surplus warehouse. Visitors can choose to follow the tour guide or opt for a self-guided experience of the site. There is also a museum on the island where you can learn about the history of the island.

Rhinebeck Car Show

Dutchess Fairgrounds, Rhinebeck
May 7–8


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Do you love cars? Of course you do! Dutchess County will host two car shows this month. The first show on Saturday, May 7 will feature hot rods, street rods, race cars, pickups, and compact customs. However, if your taste is more old-school, the show on Sunday, May 8 may be more your speed. The second car show will focus on unmodified antique and classic vehicles. Cars compete in over 60 classes for first, second, and third prize.

Apple Blossom Festival

Barton Orchards, Poughquag
May 7–8, 14–15


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There’s nothing quite as beautiful as a tree blossoming in the springtime. Except, that is, for an entire orchard full of trees in bloom! Come along to Barton Orchards for live music, games, family-friendly entertainment, and an unbeatable view of the apple blossoms. If you find yourself hungry or thirsty, stop by the taproom for some fresh cider or one of the food trucks for a bite to eat.

Live Music on the Elmendorph Green

Elmendorph Inn, Red Hook
May 28


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The summer concert series at Historic Red Hook makes a return in 2022. Kicking off the season is the Eugene Tyler Band, a high-energy bluegrass group known for its irreverent songs and skilled musicianship. Spread out your picnic blanket or set up your lawn chair and enjoy a live performance outdoors

Orange County

The Little Things Symphony Performance

Aquinas Hall at Mount St. Mary College, Newburgh
May 7, 7:30 p.m.

In contrast to The Long Shadow, which is comprised of two large works, this performance is more of a “tasting menu.” The Greater Newburgh Symphony Orchestra will perform a collection of “unusual delights,” spanning from Debussy’s Petite Suite to the sonic portraits of William Grant Still. Tickets are available online, ranging in price from $25-50, though students may attend the performance free of charge.

Car Show and Food Truck Festival

Goshen Historic Track, Goshen
May 22, 10 a.m. – 3 p.m.

Get ready for an afternoon of vintage automobiles, music courtesy of DJ Hot Rod, and unbeatable food (and desserts)! If you are interested in registering your vehicle for the car show, you may do so online for $15. In the case of rain, the festival will be moved to May 29.

Triple Threat Truck Festival

Orange County Fair Speedway, Middletown
May 27–29

Join the “Diesels of New York” group for a Memorial Day weekend of family-friendly debauchery activities at the Speedway. The festivities include a tug-of-war between trucks, a burnout contest, a pig roast, fireworks, live music, and a bull riding rodeo. Single-day passes are $25, whereas passes for the entire weekend run $50. Kids 12 and under may attend for free so long as they are accompanied by an adult.

Putnam County

Kingdom Faire

Putnam Valley (parking at 600 Lee Boulevard, Yorktown Heights)
April 30 – June 26, 10 a.m. – 7 p.m. (open weekends & Memorial Day)


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Pick a side in the battle between royalty and rogues at the Kingdom Faire! This joyous festival will feature live theatrical performers like Circus Siren Pod—a group of water artists—and Pyro Department—a talented cast of fire benders—immersing you in a world of “piratical fantasy.” Whether comedy, music, or acts of daring be yer cup of tea, the Kingdom Faire likely has something for you. Regular admission tickets start at $15, with discount options available for families and season pass holders. Patrons are asked to park at 600 Lee Boulevard, Yorktown Heights, and ride the shuttle to the grounds.

Putnam History Hike

Fahnestock State Park, Carmel
May 7, 10 a.m. – 5 p.m.

Are you interested in how parklands are selected? Dan Ricci, the Putnam Valley town historian, will discuss Native American history, the American Revolution, the discovery of iron within the park, and so much more on the eight-and-a-half-mile hike of Sunk Mine Road. Be sure to wear your hiking boots, and beware of the hike’s length and difficulty. You may register online, and the cost of attendance ranges $8-10.

Modern Makers Market

St. Mary’s Episcopal Church, Cold Spring
May 14

modern makers market

Photo courtesy of Putnam County Tourism

If you’re looking to add a touch of the Hudson Valley to your home or office space, consider shopping at this market, which will feature over 40 designers, artisans, and artists. The work available for purchase includes woodwork, glass items, jewelry, ceramics, soap, candles, spirits, and so much more. After the market, consider walking to Cold Spring’s Main Street, where you will find restaurants and storefronts aplenty.

Rockland County

Suffern Spring Street Fair

Lafayette Avenue, Suffern
May 1, 10 a.m. – 5 p.m.

May events

Photo courtesy of Rockland County Tourism

Rain or shine, spend your day in the heart of Suffern with craft vendors, live music, food, inflatables, karaoke, a beer garden and more. There will be a kid’s zone befit with a bouncy house and mini golf, along with a face painter and balloon artist near the gazebo. Don’t worry, adults—we didn’t forget about you! The beer garden opens at noon, and attendees can look forward to live music, beer pong, cornhole, food, and beer. This fair has a little something for everyone.

Tom Chapin & Friends in Concert

Turning Point Café, Piermont
May 15, 4 p.m.


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Tom Chapin, winner of three Grammy Awards, takes the stage at Turning Point Café. Many household names have performed at the Turning Point, namely Arlo Guthrie, Kris Kristofferson, John Mayall, and Janis Ian, just to name a handful. Tickets to see Tom Chapin run $42 and are held at will call.

Garner Arts Festival

Garner Arts Center, Garnerville
May 21–22, 12–6 p.m.

May events

Photo courtesy of Rockland County Tourism

For the first time since 2018, this immersive arts festival returns in the historic hamlet of Garnerville. Now in its 16th year, the festival offers world-class art exhibitions, large-scale installations, open studios, artisan demonstrations, live music, crafts, performances, craft beverages, food, and more. There is a youth art activity station just for kids, and an art show featuring work from students in Rockland and Westchester.

Ulster County

Tulip Festival

Mohonk Mountain House, New Paltz
April 25 – May 8

This celebration of flora is a staple in Ulster County, but, this year, the Mountain House has added a twist to the festivity; among the 20,000 tulips are works of art created by students in SUNY Ulster’s sculpture program. Fourteen students lent their talent to craft wire sculptures of insects, adding a whimsical element to an already one-of-a-kind experience. This is truly a collaboration between human beings and nature!

Opening Day of “Sewing in Kingston”

Reher Center for Immigrant Culture and History, Kingston
May 7


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This event is perfect for anyone interested in expanding their knowledge of history in the Hudson Valley, especially as it relates to the garment industry. See for yourself the importance of the immigrant community in Kingston and the imagination of artists past and present. Adult and family gallery tours will be available in English and Spanish.

Woodstock Rock Art and Poster Show

Bearsville Theater, Woodstock
May 13

Surely, you know that Woodstock has a rich history in the world of rock and roll. Promotional art and posters are a great way to celebrate and admire that history. At the WRAPS, attendees can view and purchase vintage posters as well as modern artwork and photography. There will be live music, multi-media productions, seminars, and workshops throughout the event. Take a step back in time to the psychedelic ’60s with this one-of-a-kind show.

Woodstock-New Paltz Arts & Crafts Fair

Ulster County Fairgrounds, New Paltz
May 28–30

This biannual fair—held in one of the Hudson Valley’s main artistic hubs—presents exceptional, juried creations by over 200 artists and craftspeople from across the country. Featured work includes furniture, photography, leather work, fine art, architectural crafts, jewelry, specialty foods, healthcare products, and more. Tickets are available online: $8 for seniors, $9 for adults, and free admission for children under 12.

Westchester County

Octagon House Home and Landscape Tour

The Armour-Stiner House, Irvington-on-Hudson
April 28 – June 27


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This structure is the only known replication of Donato Bramante’s 1502 Tempietto in Rome, making it one of the most unique homes in the world—and certainly the Hudson Valley! The architectural properties of the building harken back to a Tholos (in other words, an ancient classical temple). Within, you will also find the only remaining Egyptian Revival Room in America with original decoration and furniture. For a limited time, the Octagon House is open to public tours.

The World of Frida

Hudson River Museum, Yonkers
Open through May 22

This exhibition “celebrates the culture, style, and persona” of the Mexican painter Frida Kahlo, whose stature in the art world is rivaled by few. The show features work by more than 75 artists, either employing Kahlo herself as their subject or drawing from her singular visual vocabulary. Viewers can expect references to her self-portraiture, her love affair with muralist Diego Rivera, and her feminist identity.

Teatown PlantFest

Teatown, Ossining
May 6, 3–7 p.m., and May 7, 9 a.m. – 2 p.m.


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Looking to bolster your garden? Come on down to PlantFest, where you will find inspiration, advice, and—most important of all—new plants that will bring your home garden to the next level. The greenest of green thumbs should consider coming on Friday for the “First Pick,” during which attendees may choose from a curated selection of plants.


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