An Insider’s Guide to May 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 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 your pup is itching to get out and about as well. 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

Lupine Festival

Albany Pine Bush Preserve, Albany
May 1–31

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The Capital Region is host to the Pine Bush Preserve, where nature lovers can discover the rare Karner blue butterfly flitting and fluttering through fields of violet lupine flowers. It’s truly a sight to be seen, and visitors can also look forward to hands-on activities, live music, games, and craft beer and food vendors at this month-long event.

76th Annual Tulip Festival

Washington Park, Albany
May 11 & 12, 11 a.m. – 6 p.m.


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Returning for its 76th year, Albany’s Tulip Festival is back for Mother’s Day weekend. Explore garden beds of more than 140,000 tulips in 150 different varieties, shop nearly 100 artisans selling handmade crafts, and enjoy a fine arts show, delicious food, kid’s activities, the crowning of the Tulip Queen, the Capital Region’s Best Mom Ceremony, and two stages of entertainment with headliners, including The Front Bottoms.

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Schuyler Mansion State Historic Site, Albany
May 18, 11 a.m. – 4 p.m.

Once a colonial Dutch holiday, Pinkster is an 18th-century tradition that has developed into an African celebration of family, hope, and culture. Pinkster became a spring celebration during which enslaved men and women would reunite with friends and loved ones and participate in storytelling, music, dance, food, and the crowning of the Pinkster King. The celebration at the Schuyler Mansion will feature musical performances, participatory dance, live music, fabric stamping, food, open-house tours of the mansion, and more.

Columbia County

Hudson Children’s Book Festival

Harry Howard Avenue, Hudson
May 4, 10 a.m. – 3 p.m.

In the heart of historic Hudson, the Hudson Children’s Festival has been held since 2009. The festival aims to create, sustain, and nurture a culture of literacy in partnership with the surrounding community and schools. The event is free for families and children to come see authors and illustrators as they browse books and other literature.

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24-Hour Drone

Basilica Hudson, Hudson
May 18, 12 p.m. – May 19, 12 p.m.


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This immersive event at Basilica Hudson is an all-encompassing experience that includes 24 hours of unbroken music. The international series features musicians and sound artists experimenting within the space to create 24 hours of continual sound. The event is an experimental event that pushes the boundaries of what a communal and conceptual experience can be.

Hudson Berkshire Wine Festival

Columbia County Fairgrounds, Chatham
May 25 & 26

Explore family-owned farms and businesses as you sip through their hand-crafted wines and spirits. The unique, interstate festival will feature award-winning local wineries, distilleries, and cideries under one roof. Along with beverages, there will be displays by local crafters, jewelers, and artisans, as well as gourmet cheeses, olives, pickles, jams, maple syrups, baked items, and more.

Dutchess County

Silver Needle Runway Fashion Show

Marist College, Poughkeepsie
May 3, 7 p.m.

A student-run fashion show presented by Marist College’s Fashion Department, the Silver Needle Runway is an annual showcase of student-designed garments and creations. For this year’s 38th annual Silver Needle Runway, the theme is “Interlinked,” which invites spectators to relinquish meticulous control over their lives in favor of embracing the greater idea of humans and everything around them.

Hudson Valley Theatre Festival

Throughout Dutchess County
May 3–5

Presented by the New Deal Creative Arts Center, the Hudson Valley Theatre Festival is three days of performances throughout the Hudson Valley region, including Dutchess County. The festival is a celebration of new theatrical works, supporting playwrights by providing opportunity and accessibility to established and emerging local, national, and international talent.

Pride in the Sky

Walkway Over the Hudson, Poughkeepsie
May 17, 6 p.m.

Kick off Pride season in the Hudson Valley with the Walkway Over the Hudson’s first-ever Pride Night. The evening will be highlighted by the Walkway’s new LED lighting system, which will glow a vibrant rainbow in honor of Pride. As a part of the celebration, a DJ-driven dance party will be going all night long at the center of the Walkway.

Orange County

Spring Breakout Carnival

Blue Arrow Farm, Pine Island
May 1–5


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Fair and carnival season has commenced in the Valley! In Pine Island, welcome spring by making memories with the family at the Spring Breakout Carnival. Enjoy rides, games, music, classic midway food, and treats for the whole family. Admission is $5 for adults and free for children under 18. All proceeds go to animal rescue.

Original Flea Outdoor Market

Newburgh Vintage Emporium, Newburgh
May 4, 9 a.m. – 6 p.m.

Legend has it that the first outdoor flea market in the United States was held in Newburgh in 1752. Carrying on tradition, the Original Flea Outdoor Market features more than 30 local makers, vintage and antique dealers, food trucks, and other treasures on the parking lot and grounds of the Newburgh Vintage Emporium.

Mother’s Day Brunch

The Thayer Hotel, West Point
May 12, 10:30 a.m. – 2:30 p.m.

Celebrate mom at the historic Thayer Hotel this Mother’s Day with a very special brunch. Enjoy gorgeous views of the Hudson River while you indulge in a delicious meal with the whole family. The menu includes everything from spring veggie salads to breakfast classics to fresh seafood, followed by some sweet dessert offerings.

Putnam County

Hops on the Hudson Makers Market

St. Mary’s Episcopal Church, Cold Spring
May 4 & 5, 11 a.m. – 5 p.m.


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Head to Cold Spring to browse over 60 artisans, food trucks, and live music at the Hops on the Hudson Makers Market. The event is outdoors on the lawn of the church, where picturesque views of the Hudson can be seen.

Please note the new parking system in Cold Spring: The year-round meter system, along with the residential parking program being enforced on side streets, began April 5 and requires visitors to pay to park on Main Street from 10 a.m. to 6 p.m., Friday through Sunday, as well as on Monday holidays. Metered parking on Main Street will cost $4 per hour for a maximum of three hours, with payment by credit or debit card through the ParkMobile phone app or at kiosks in front of Village Hall and near the corner of Main and Church streets.

History Hike: Denny Mine

Fahnestock State Park, Carmel
May 18, 10 a.m. – 12 p.m.

Join the Putnam History Museum on this guided History Hike exploring Fahnestock State Park and the Denny Mine. While exploring the surrounding Denny Mine area, the guided hike will touch upon the discovery of iron within the Putnam County area and the role the mines played during the Civil War. The hike is moderately difficult.

Red Rooster Drive-In

Throughout May


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What started as a simple summertime custard stand has turned into a Putnam County mainstay in Brewster since 1963. It’s never a bad time for ice cream, and Red Rooster has it all from classic burgers to crispy fries to old-fashioned shakes. If it’s a nice enough day, head outside to the mini gold course adjacent to the patio.

Rockland County

Music Sessions at ROCA Presents: Kate Taylor

Rockland Center for the Arts, West Nyack
May 4, 7:30 p.m.

This evening of music at Rockland Center for the Arts welcomes singer-songwriter Kate Taylor for a special show. Taylor is an American artist and the younger sister of renowned musician James Taylor, a six-time Grammy winner. Join other locals for this can’t-miss music session.

Mother’s Day Brunch

Bear Mountain Inn, Tomkins Cove
May 12, 10 a.m. – 3 p.m.


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This May, give mom the culinary gift she deserves at the Bear Mountain Inn. Head to the Inn’s Restaurant 1915 for a brunch featuring traditional morning cuisine, specialty cocktails, and delicious desserts in the unique and historic setting within Bear Mountain State Park. There will be three seatings at 10 a.m., 12:30 p.m., and 3 p.m.

Hudson Valley Maker Faire

Garner Arts Center, Garnerville
May 18 & 19, 12–6 p.m.

For its second year, the Hudson Valley Maker Faire returns to the Garner Arts Center this May. The event showcases the visionary projects and work of regional makers, artists, and artisans. Throughout the weekend, take part in interactive workshops and technology demonstrations, or visit open artist studios to see immersive installations. Local craft food and beverages will be available to enjoy along with live music and performances.

Related: Where to Celebrate Cinco de Mayo in the Hudson Valley

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