May Events to Check out in the Hudson Valley

A film fest in Pleasantville, wine and food fest in Chatham, and more are top picks for May.

A Plethora of Plants: Real, Observed, Imagined

North Salem

Plants have inspired artists for centuries; at the Hammond Museum, come see a group exhibition of paintings, drawings, photographs, videos, and more that honor flora by contemporary makers. In addition to visual arts, the exhibit includes live plants, a soundscape, and plant-based fragrances.

Excellence in Nursing

May 1, 6–10 p.m.

Join Hudson Valley at The Grandview as we honor our region’s top nurses with a night of food, drinks, music, and dancing. Tickets can be purchased online for single attendees or tables of 10.

Hudson Children’s Book Festival

May 4

Hudson Junior-Senior High School hosts a group of authors, illustrators, local vendors, and more to promote literacy and the joy of reading. Admission is free.

- Advertisement -

Rock the Ridge

New Paltz
May 4

Lace up your kicks for a good cause—Rock the Ridge challenges individuals and relay teams to run or hike a 50-mile course within 18 hours to fundraise for the Mohonk Preserve. The route begins at the Testimonial Gateway structure and takes participants through the Shawangunk Ridge.

Native Prospects: Indigeneity and Landscape

Opens May 4

In this exhibition at the Thomas Cole National Historic Site, historic and contemporary works by Indigenous artists are juxtaposed with landscape paintings by the eponymous Hudson River School founder. Modern artists such as Teresa Baker, Kay WalkingStick, and Brandon Lazore will be displaying pieces.

Native Prosepcts
Photo by Kay Walkstingstick / Courtesy of Thomas Cole NHS

Spring Apple Blossom Festival

May 4–5 and 11–12, 10 a.m.–4 p.m.

Head to Hurds Family Farm to celebrate the arrival of spring blooms that will turn into apples available to pick come fall. Visitors can view the farm in one of three ways; a drive-through experience, a golf cart tour, or a self-guided walking tour that includes access to food vendors and kid’s activities.

Hudson Valley Marathon at the Walkway Over the Hudson

May 5

This marathon takes runners across the Walkway Over the Hudson pedestrian bridge and through local rail trails. A one-mile fun run, 5K, 10K, and half marathon will also be offered.

Improv Comedy at Two Way

May 11, 8 p.m.

Every second Saturday, Two Way Brewing hosts performers from Serious Comedy Theatre for a night of craft brews and hearty laughs. Tickets are $10 per person and are available online and at the door.

- Partner Content -
May tulip festival
Adobe Stock / jonbilous

Tulip Festival

May 11–12

Returning for its 76th year, Albany’s famous Tulip Festival is a two-day celebration of spring and the city’s Dutch heritage. In and around Washington Park, catch live music, a street sweeping ceremony, food vendors, and over 140,000 colorful tulips.

film center
Photo courtesy of the Jacob Burns Film Center

Film Preservation Festival

May 13–23

Love old movies? Head to the Jacob Burns Film Center (JBFC) in Pleasantville this month for “Restored & Rediscovered: A Film Preservation Festival.” During the week of May 13–19—with additional showings May 20–23—you can view newly-restored classics, short films, and documentaries, including Martin Scorsese’s Academy Award-winning “Hugo,” Edward Yang’s 1996 comedy “Mahjong,” and Nancy Savoca’s 1993 family saga “Household Saints.” In addition to the screenings, JBFC will have panels and presentations to education audiences on film restoration. Before grabbing a theater seat, check out JBFC’s recently opened Take 3 Wine Bar and Café on the third floor, which offers fine wines, craft beer, non-alcoholic drinks, and small bites. – Tess Foley-Cox

Jacob Burns Film Center
Photo courtesy of the Jacob Burns Film Center

HITS Spring Series

May 17–19

For 20 years, HITS Saugerties has welcomed equestrians to its grounds for nine weeks of fun events and competitions. The season kicks off at the spring premiere with hunter and jumper horse shows that are open to the public and free to watch.


May 17

Elysium Furnace Works presents a performance by Chourmo in the VBI Theatre at the Cunneen-Hackett Arts Center. The jazzy trio is made up of guitarist David Torn, sax player Tim Berne, and drummer Tom Rainey.

Sonia de Los Santos

May 19, 2 p.m.

This family-friendly concert by Mexican musician Sonia de Los Santos will be held outdoors at Caramoor’s Friends Field. Singing in both English and Spanish, De Los Santos plays songs about friendship, hope, connection, and more. Attendees are encouraged to bring their own blanket or lawn chairs.

- Advertisement -
Sonia de Los Santos
Photo by Gabe Palacio

Watercolor Values Workshop

May 25, 1–3 p.m.

Want to experiment with watercolors, but not quite sure where to start? Consider this beginner’s class at KinoSaito which takes artists through the basics of the medium and color theory to create a still-life painting. RSVP online for the workshop taught by Lilly Gummerson.

Hudson Berkshire Wine, Food & Craft Festival

May 25–26

At the Columbia County Fairgrounds, wineries, cideries, and distilleries from the Hudson-Berkshire Beverage Trail will convene to display and sell bottles. In addition to tastings, enjoy special seminars from local beverage professionals and buy gourmet goods from nearby farms.

Woodstock-New Paltz Art & Crafts Fair

New Paltz
May 25–27

The Ulster County Fairgrounds come alive during Memorial Day Weekend for this biannual fair. Shop a wide selection of handmade jewelry, ceramics, prints, woodworking projects, and more, plus a food court with local offerings and a craft tent for kids.

Field + Supply Spring MRKT

May 31–June 2, 10 a.m.–6 p.m.

Hutton Brickyards welcomes this biannual modern maker’s market to its riverside grounds. Ticketholders can peruse the wares of over 275 vendors, enjoy food from local restaurants, and listen to live music.

All One One All Farm


All One One All Farm
Courtesy All One One All Farm

Goshen’s All One One All Farm opened for its fourth season on April 5—with some new perks. Beyond the organically grown produce at the farmstand and unique workshops (like wool spinning and herbal medicine), they debuted a farm-forward, small-batch distillery. “Just like we sell eggs from our pasture raised heritage hens and produce from the veggie garden, we have begun to concoct artisanal liqueurs made with nuts, herbs, fruits, and vegetables from our farm,” says project director Alix Daguin. A line of five liqueurs—from crème de menthe to anisette—and fruit brandies will be available on weekends. You can buy bottles or enjoy them in cocktails like Tipsy Fizzes and Moscow mules. “The distillery is not only a delicious way to make the most of our abundant harvest, but it makes for a fun new offering for our visitors, too.” For more information, visit – Francesca Furey

Hudson Valley Shakespeare Festival

Rendering by Studio Gang

The Hudson Valley Shakespeare Festival (HVSF) is getting new digs. Thanks to a $10 million grant from the New York State Council on the Arts, the HVSF will begin construction on an eco-friendly 13,850-square-foot open-air theater with Chicago-based urban design company Studio Gang. The new theater, scheduled to be completed in 2025, will have natural ventilation, rooftop solar panels, and stunning views of the Hudson River, Breakneck Ridge, and Storm King Mountain. – Eli Nussbaum

Shakespeare theater
Rendering by Studio Gang

Related: Here’s What to Do in the Hudson Valley This Week

Our Digital Partners

Learn how to become a digital partner ...

Our Excellence in Nursing Awards take place on May 1!

Our Best of Hudson Valley ballot is open through March 31!

Unveiled: A Boutique Bridal Brunch is February 25!

Holiday flash sale ... subscribe and save 50%

Limited time offer. New subscribers only.