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

Photo courtesy of Ulster County Tourism

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. Even in the face of the coronavirus, there exist dozens upon dozens of ways to experience the best of what the region has to offer. While they might not be traditional per se (Mother’s Day brunch to-go, anyone?), they are engaging, entertaining, and 100-percent #flattenthecurve-approved. P.S. Hudson Valley Restaurant Week, running May 10-23, showcases some of the best cuisines in every county.

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

Discover Albany President and CEO Jill Delaney shares her top recommendations for the month.


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Virtual Albany Tulip Festival

Online, Albany
Throughout the month of May

April showers are bringing May flowers in Albany. Celebrate the peak of spring with a series of interactive virtual events. Take an online tour of blooming tulip beds with the City of Albany Gardeners and learn about the care required to raise such gorgeous plants. Watch engaging musical performances from local artists in unique locations throughout the city, and follow the schedule of games to play with the kids. The Tulip Festival will announce prizes throughout the month.


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I Love You, You’re Perfect, Now Change!

Cohoes Music Hall, Cohoes
Through May 23

Plan a date night out to the theater again at Cohoes Music Hall. Playhouse Stage Company welcomes audiences back to this iconic Capital Region venue with “I Love You, You’re Perfect, Now Change!” This musical comedy romp is one of the longest-running off-Broadway shows in history. Relatable, hilarious, and always entertaining, this play pokes apart the ups and downs of relationships through a series of vignettes. Secure your ticket online, and enjoy a safe and fun live entertainment experience.

Earth, Wind, and Weave

Pine Hollow Arboretum, Slingerlands
Throughout the month of May (Special meditation walk May 19)

Art and nature often intersect in the form of installations in the Hudson Valley. “Earth, Wind, and Weave” takes visitors through the beautiful trees of the Pine Hollow Arboretum, showcasing the multi-dimensional weaving. Each panel utilizes a mixture of yarn and upcycled materials, like bathing suits. Visit the open-air exhibit throughout the month of May to enjoy the scenic environments of the Hudson Valley. On May 19, take a guided meditation walk with the artist herself, Lori Kochanski.

Columbia County

Read up on Columbia County Tourism’s highlights for things to do in the Hudson Valley this month.

Tree Walk

Photo courtesy of Columbia County Tourism

Spring Tree Walk

Olana State Historic Site, Hudson
May 22, 1 p.m.

May is the perfect time to explore the many unique historic places of the Hudson Valley. With this springtime tree walk, explore the meticulously designed landscape of Olana. Frederic Church’s masterpiece features several unique species of trees, and this tour will help you learn how to identify them. Members of the Hawthorne Valley Farmscape Ecology Program lead this event and grant insight into every type of vegetation native to Olana’s majestic grounds.

Dutchess County

Dutchess Tourism President and CEO Melaine Rottkamp shares her top recommendations for the month.

Apple Blossoms

Photo courtesy of Dutchess Tourism

Apple Blossom Festival

Barton Orchards, Poughquag
May 1-2 & 8-9

Barton Orchards may be an autumnal paradise, but this iconic destination has a distinctive beauty in the spring. Before farm-fresh apples are ready to be picked off the trees, a colorful array of apple blossoms bespeckle their branches. Live music, a petting zoo, and more make this event fun for the entire family. For those 21 and over, Barton Orchard pours fresh cider from its tap room. Plus, attendees can sample delicious fare from local vendors.

Hudson Valley Renegades

Photo courtesy of Dutchess Tourism

Hudson Valley Renegades Home Opener

Dutchess Stadium, Beacon
May 11, 7 p.m.

This season of baseball at “The Dutch” will be like no other. The Hudson Valley Renegades return, this time as High-A Yankee affiliates. Fans of the Minor League team can secure tickets for their home opener this May. All social distancing protocols will be adhered to, with small group tickets available. Come back on May 28 for the first fireworks show of the summer. Visit the Hudson Valley Renegades website for a complete season schedule.

Barn Star’s Spring Antiques at Rhinebeck

Dutchess County Fairgrounds, Rhinebeck
May 29-30

Antique lovers and history nuts alike will adore this annual Hudson Valley event. Barn Star’s Spring Antiques at Rhinebeck puts together an array of artifacts, accessories, and more. Explore local history through Native American jewelry, folk art, and pottery or take a global approach with Asian rugs and European textiles. This hybrid vintage market and historical exhibit spreads across three large buildings at the Dutchess County Fairgrounds. The venue is well-ventilated, and social distancing will be observed.

Greene County

Look no further for the coolest attractions and activities in Greene County during the month.

Spring Lights at the Thomas Cole Historic Site After Dark

Thomas Cole National Historic Site, Catskill
May 1,2,7,8,9

If the view from the Thomas Cole Historic Site wasn’t impressive enough during the daytime, you have to see the new nighttime experience planned for the artist’s home. Titled “Spring Lights,” this event illuminates the walking path around the iconic grounds. Visitors will see a building-wide projection of light and sound, referencing the vast body of work completed by the Hudson River School of Art’s founder. Visit the website to secure tickets to this evening experience.


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Diamond Motocross

Diamond Motocross, East Durham
May 8 & 9

Motocross racing in the Catskills is a uniquely exciting experience, and East Durham is the place to be for high-octane competition. Cheer on seasoned racers at Diamond Motocross as they zoom around the rustic track. Watch them prepare in open practice on May 8 or go head-to-head on May 9. A challenging course, scenic landscape, and other entertainment will keep visitors engaged at this one-of-a-kind mountainside experience.

Mountain Top Arboretum Events

Mountain Top Arboretum, Tannersville
Throughout the month of May

Tannersville’s marvelous base for wildlife education and hiking alike, Mountain Top Arboretum has plenty to offer Hudson Valleyites during the month of May. The family-friendly “Story Walk in the Woodland” series runs from May 8-15. Talk a walk through the idyllic wooded paths of the Catskills and enjoy readings from cute and folksy children’s stories. On May 29, bird enthusiasts will get a special treat. Audubon Society educator Larry Federman will teach guests how to find warblers, bluebirds, and other migrating birds native to the northern Hudson Valley.

Orange County

Check out Orange County Tourism Director Amanda Dana’s selections for the best things to do this month.

The Original Flea Outdoor Market

Newburgh Vintage Emporium, Newburgh
May 8, 10 a.m. – 6 p.m.

According to local legend, the first outdoor flea market in the nation’s history was held in Newburgh back in 1752. Pay tribute to a bygone era at the Newburgh Vintage Emporium. The open-air version features 40 local vendors and food trucks galore. Record dealers, antique sellers, craft artisans, and more showcase the best of regional goods. When the weather in the Hudson Valley is so gorgeous in May, there’s no reason to stay inside during a shopping spree.

Mother’s Day Brunch at Christopher Jacobs Winery

Christopher Jacobs Winery at Pennings Vineyards, Pine Bush
May 9, 12:30-3 p.m.

Treat moms to a gorgeous outdoor brunch filled with top-rated wines at this idyllic locale. Christopher Jacobs Winery is nestled in the hills of the Hudson Valley, offering breathtaking views of the region. A meal for two includes a variety of quiches, farm-fresh salads, a complete wine tasting, and decadent dessert. Regional beer and cider will also be served fresh from the tap. The brunch special is $60 per pair and requires a reservation.

Spring Fest Game Dinner & BBQ

Long Lot Farm Brewery, Chester
May 15 (Rain date May 22)

Enjoy sampling adventurous eats? Long Lot Farm Brewery’s annual wild game dinner returns, featuring a Hudson Valley specialty, venison. The gamey ragout is a classic recipe from the Silver Fox Sportsmen Association, which hosts the yearly event. Long Lot hosts the foodie extravaganza at its scenic brewery, and provides tons of fresh brews on tap. Live music, prizes, and a 50/50 raffle sweeten the deal. Come with an open mind and an empty stomach for creative cuisine and local tradition.


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Cruise to the Drive-In

Warwick Drive-In, Warwick
May 22, 9 a.m. – 3 p.m.

A full day of fun awaits at an old-school drive-in in Warwick. Hosted by Dead Mans Curve, locals can experience the heightened atmosphere of a classic car show as hot rods that pre-date 1972 parade through the grounds. DJ Jim FunZul, a strolling magician, and more entertainment keeps everyone present engaged leading up to the movie. Once the showing is over, the party continues over at Blue Arrow Farm with live music, delicious fare, and more.

Putnam County

Read up on Putnam County Tourism Director Tracey L. Walsh’s picks for things to do this month.


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Pontoon Boat Rentals

Lake Mahopac, Mahopac
Throughout the month of May

There are fewer places better to enjoy warm weather than on the water. Relax on the gorgeous Lake Mahopac with a peaceful pontoon boat. These vessels, which can hold up to 12 people, are rented out for the entire day. Through Mahopac Marine rentals, families and friends can gather for calm days out on the water. Boats book up fast, so make your reservation online and in advance to secure your pontoon.

Magazzino Italian Art

Photo courtesy of Putnam County Tourism

Nivola: Sandscapes

Magazzino Italian Art, Cold Spring
Starting May 8

Returning to more regular hours, Magazzino Italian Art debuts Nivola: Sandscapes. This special exhibit emphasizes the pioneering process of sandcast sculptor Costantino Nivola. The Sardinian artist worked through the ’50s, ’60s, and ’70s, carving concrete sculptures, completing architectural commissions, and more. Nivola’s range of artistic mediums is beyond impressive, and his proficiency in each is even harder to replicate. He left an indelible impression on modern architecture; explore the body of work anytime after May 8.



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Celebrate Design at Manitoga

Manitoga, Garrison
Starting May 14

Celebrate the arts at The Russel Wright Design Center, opening for visits May 14. Immersive tours through Manitoga’s landscape explore the architecture and collections. One tour, a mindful outdoor experience, follows nature guide Jane Dobson in the traditional practice of Japanese forest bathing. This method of meditation serves as a preventative healthcare practice that contends with the stress of everyday life. In general, exposure to natural surroundings reduces blood pressure and heart rates, boosting immune systems along the way. Visit Manitoga for the collections or the interactive programming.



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Farm to Table: A Ride to Combat Poverty

Route through Putnam County
May 22

Tour scenic Putnam County for a good cause. The Putnam Community Action Partnership organized this initiative to bring awareness to issues of poverty and food security in the region. The route begins at Tilly Foster Farm in Brewster and winds its way through some of the Hudson Valley’s most iconic sights. Stops include Arts on the Lake, The Great Swamp Boardwalk, Lake Gleneida, Magazzino Italian Art, Boscobel House & Gardens, and many more. Travels will end at Space at Ryder Farm and feast upon a meal from Clock Tower Grille. Donations and proceeds from a silent auction will go towards Putnam CAP’s food pantry, soup kitchen, and other forms of advocacy.

Rockland County Restaurant Week

Photo courtesy of Rockland County Tourism

Rockland County

Take a browse through Director of Economic Development and Tourism Jeremy Schulman’s picks of the hottest things to do in Rockland County throughout the month.

Harriet Tubman Statue

Photo courtesy of Rockland County Tourism

See the Harriet Tubman Touring Statue

African American Memorial Park, Haverstraw
Throughout the month of May

Head to Haverstraw to see a magnificent piece of art honoring one of America’s greatest heroes. As the Harriet Tubman Journey to Freedom Statue tours the nation, it stops for several weeks in Rockland County. The nine-foot-tall statue weighs 2,400 pounds and is made of solid bronze. Tubman is depicted leading a young girl to freedom. Also stop by the park’s kiosks dedicated to the history of African diaspora in the Hudson Valley.

Grand Re-Opening Holocaust Museum and Center for Tolerance and Education

Holocaust Museum and Center for Tolerance and Education, Suffern
May 23

A long-awaited initiative in Suffern comes to fruition. The Holocaust Museum and Center for Tolerance and Education is set to complete a multi-functional space, which will serve as home to a permanent exhibition and community gathering space. The re-opening will be commemorated by a virtual ribbon cutting on May 23. The museum will unveil state-of-the-art technology and inclusive people-centered designs to ensure programs are accessible to the entire community.

Walk or Bike Across the Mario Cuomo Bridge

Governor Mario M. Cuomo Bridge, Rockland Landing
Throughout April

Have you wanted to cross the former Tappan Zee Bridge in style? Whether you enjoy brisk winter jogs or long scenic bike rides, the bridge path on the Governor Mario M. Cuomo Bridge is a must-visit. Enjoy spectacular views from themed glass platforms overlooking the Hudson River, with free audio tours available to enhance the experience. Visit six unique overlooks on your way to the Westchester side.

Ulster County

Read up on Ulster County Tourism’s event highlights for March.

Mayfest: Farmers and Makers Market

Walkway Over the Hudson, Highland
May 8-9

How great would it be to do some shopping right after a stroll across the Walkway Over the Hudson? The Mayfest Farmers and Makers Market curates a collection of the region’s finest breweries, wineries, restaurants, artists, artisans, and much more. Over 80 vendors will set up throughout the Hudson Valley Rail Trail, and art installations welcome visitors to the Highland side of the Walkway. Tastings of local wines and craft beer will be available through online tickets.

Ulster Opus 40

Photo courtesy of Ulster County Tourism

Free Community Day at Opus 40

Opus 40, Saugerties
May 15, 11 a.m. – 5 p.m.

Opus 40 is one of the Hudson Valley’s incredible outdoor sculpture parks. On May 15, the team at Opus 40 gives back to local residents with free entrance all day. Each time slot for visitors is two hours long. This annual spring ritual also features live accordion music, performers from Bindlestiff Cirkus, and more entertainment. In addition to food and drink, seed and planting sales will also take place onsite. Visit the website to make your reservation.


Courtesy of Ulster County Tourism. Photography: Steve Aaron

Spring Stroll

May 28-31

Dive into the rich heritage, historic sites, and bustling shops that Kingston has to offer. Stroll along the eclectic sidewalk sales organized by local business owners and artists. This weekend exploration will lead visitors to the quaint Rondout waterfront and through Uptown’s storied Stockade neighborhood. Outdoor dining from sidewalk vendors, flash sales at storefronts, and tons of biking, walking, and hiking await in Ulster County’s most historic city.

Woodstock-New Paltz Art and Crafts Fair

Field of Dreams Park, New Paltz
May 28-31

Back for its 40th anniversary, the Woodstock-New Paltz Art & Crafts Fair features work from juried artists, apothecary products, and wines, beer, and spirits from the Hudson Valley. Live music fuels the atmosphere, always entertaining due to its ongoing demonstrations and children’s activities. The Art & Crafts Fair’s outdoor locale keeps the experience both safe and comfortable, taking advantage of gorgeous late-May weather.

Westchester County

Discover the hottest happenings according to Westchester County Tourism this month.

Jacob Burns Film Center Reopens

Jacob Burns Film Center, Pleasantville
Throughout the month of May

On April 30, the Jacob Burns Film Center reopened to cinema fans across the Hudson Valley. Catch up on new flicks like the Best Picture-winning Nomadland or the Tilda Swinton-led The Human Voice. If you aren’t quite ready to go back to the movies, JBFC continues with its virtual marquee movie programming.


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ArtsWestchesster Exhibit

ArtsWestchester, White Plains
Starting May 7

Experience the work of over 220 Hudson Valley artists at this White Plains exhibition. ArtsWestchester announces “Together apART: Creating During COVID,” a reflection of the shared pandemic experience. More than 250 pieces of painting, photography, music, and other artwork speak to the similarities and differences between everyone’s lifestyle during the height of COVID-19. During a time of loss, anxiety, and solitude, creating art is a powerful method of coping with surrounding challenges. Get inspired by fellow residents of the region.

Westchester Craft Crawl

Throughout Westchester County
May 15-16

Stop along Tarrytown, Ossining, and Cortlandt Manor to explore eight studio spaces. The Westchester Craft Crawl introduces patrons to 30 professional craft artisans from the Hudson Valley. Each studio stop will be home to a few artists. Discover handmade clay pottery, metalwork, jewelry, and wooden objects. This collection of local makers is one of the largest of its kind in the entire region, and showcases vendors in a safe, socially distant manner.