May Events

Check out our list of fun things to do in Dutchess County this May. Events include plant sales, fairs, theater, live entertainment, and more!


Troutbeck Symposium 2024, AMENIA
Troutbeck and the Du Bois Forum will co-host a dedication ceremony for a new historical marker commemorating the Amenia Conferences of 1916 and 1933—two pivotal moments for the NAACP, strengthening the organization leading up to the Civil Rights Movement—both held at Troutbeck. May 1-3, 6 pm.


Pete Seeger Birthday Celebration, BEACON
On the anniversary of Pete Seeger’s birth, the Towne Crier is pleased to present a tribute in honor of an important person in the Beacon community, as well as the global community. 8:30 pm.

Tivoli First Fridays, TIVOLI
Stroll, savor, mix and mingle with local artisans, businesses and the community on the first Friday evening of every month. 

The Two Gentlemen of Verona, New Jersey, RHINEBECK
THE TWO GENTLEMEN OF VERONA, NEW JERSEY follows four Elizabethan theatre artists who are commissioned by a mysterious, wealthy patron to devise an original, hit comedy. 8 pm.

Rhinebeck Antique Car Show & Swap Meet, RHINEBECK
The Swap Meet at Rhinebeck has been a favorite among car collectors from all over the Northeast for years. There are a large number of Swap Spaces at Rhinebeck both outside and inside that consist of four large well-lighted buildings. 12 pm – 5 pm.


International Fly Fishing Film Festival, MILLBROOK
Join Orvis Sandanona Shooting Grounds for the world’s leading fly-fishing film event, consisting of films produced by professional filmmakers from all corners of the globe that showcases the passion, lifestyle, and culture of fly fishing. 5 pm.

Explore Thompson Pond, PINE PLAINS
Explore and learn about the exciting trail work going on at Thompson Pond from local experts and volunteers. The DLC, The Nature Conservancy, and Friends of Stissing Landmarks will be at Thompson Pond from 9 am to 2 pm to answer questions and provide information about the amazing things going on and how the public can work together to best support the outdoor recreation needs of our diverse community.

YCA Stissing Award Winners Showcase, AMENIA
2022 and 2023 Young Concert Artist Stissing Award Winner, Korean pianist Chaeyoung Park and American violinist Oliver Neubauer join forces to open the 2024 season for Chamber Music at TSC. 4 pm – 6 pm.

Help a Horse Day at Lucky Orphans Horse Rescue, DOVER PLAINS
The 150th Kentucky Derby, the first race of the Triple Crown, will be shared live at Lucky Orphans Horse Rescue. The pre-race celebration will feature hors d’oeuvres, beverages, games and live coverage of the pre-race. At post time, watch the Derby, cheering on their favorite horse. Watch the race LIVE at the farm, and then enjoy dinner, live music by Way Behind the Sun, dancing and drinks. 5 pm.

“I Love My Park Day”, POUGHKEEPSIE
Members of the Millbrook Garden Club and the Garden Club of Orange and Dutchess Counties will be joining thousands of volunteers across the City of Poughkeepsie and the Town of Lloyd to celebrate “I Love My Park Day”.

Meet The Director: I Like It Here, MILLERTON
A key figure of American independent documentary film, Ralph Arlyck conveys how it feels to look back on your own life, to contemplate your place in an ever-changing world, and what to make of the time that remains. 6:30pm.

KJ Denhert Band; With Special Guest Michele Gedney, BEACON
KJ Denhert is a NYC-based songwriter, guitarist, vocalist and bandleader whose soulful and smoky vocal stylings are earthy and elegant. 8:30 pm.


Hudson Valley Fair, WAPPINGER FALLS
Visit the Hudson Vally Fair! Enjoy carnival rides, food trucks, and prizes. 12 pm – 10 pm.

Cinco de Mayo Party with Dúo Andalucía, RED HOOK
This Cinco de Mayo, get ready to set Sabroso Mexican on fire with the sizzling sounds of Duo Andalucia! Sabroso Mexican Restaurant starting at 11 am.

Rattlesnake Run, WASSAIC
The Wassaic Project is proud to sponsor this free fun run of different distances (11 miles, 7 miles, 5 k) along the Harlem Valley Rail Trail. Choose between 3 starting points, and run down to downtown Wassaic! 10 am – 12 pm.


There’s no Zumba without U! Take the Zumba class at the Center for Performing Arts in Rhinebeck with Miss Jessie on Tuesday from 6 pm – 6:45 pm. This class is specifically designed for those who need a little more energy and positivity in the form of exercise without the dread of exercise!

MAY 10

Little Shop of Horrors, RHINEBECK
May 10-26, CENTERstage Productions is proud to present the hit musical comedy, Little Shop of Horrors with music by Alan Menken, book & lyrics by Howard Ashman. 7:45pm.

Gratefully Yours, BEACON
Gratefully Yours has quickly established itself as one of the Northeast’s premier Grateful Dead tribute bands; with a truly all-star lineup and often performing “dream” set lists submitted by their fans. 8:30pm

Food Pop-Up: Fat Apple Farm Smoker, RED HOOK
Fat Apple Farm is a sustainable, ethical livestock farm in Pine Plains, NY, raising entirely grass fed cows and sheep, and organic grain fed pigs. Enjoy the farm and the food pop-up 4 pm – 8 pm.

MAY 11

Mother’s Day with the Cows, WINGDALE
Will visit the cows with their new calves and announce the winning names for the newest members of the herd! 10am-11:30am.

Best Friends Girl, BEACON
Best Friends Girl recreate the timeless hits of The Cars spanning a 35-year career, with over 23 million albums sold and having more than 22 songs on the Billboard top 100. 8:30 pm.

Tea for Three: Lady Bird, Pat & Betty, AMENIA
Particularly pertinent in an era of heightened politics, TEA FOR THREE humanizes the political scene with a story both whimsical and deeply moving – a behind-the-scenes look at Lady Bird Johnson, Pat Nixon, and Betty Ford. Share the journey of each as they deal with the fishbowl of First Ladydom. 3 pm and 7 pm at the Stissing Center.

The Hudson Valley Hoedown, DOVER PLAINS
Saddle up with the 2024 Leadership Dutchess class for a rollicking good time at Lucky Orphans Horse Rescue in Dover Plains, NY. Enjoy country music, line dancing, delicious food and drink, and test your mettle with a mechanical bull ride. 6 pm – 9 pm.

MAY 12

Mother’s Day 2024 Watercolor Workshop with Jaime Reynolds, AMENIA
Watercolor artist Jaime Reynolds will be instructing on the basics of watercolor painting from 12-3pm. Sign up so that they expect you, but drop in whenever you’d like between 12 pm – 3 pm, before or after Mother’s Day Brunch.

MAY 17

Renegades Minor League Baseball, WAPPINGERS FALLS
Head over to Heritage Financial Park to watch the Hudson Valley Renegades vs the Jersey Shore. 7:05 pm.

The Englishtown Project, BEACON
This tribute extravaganza, The Englishtown Project, will feature healthy “doses” of selections from each band’s sets that day along with other deep cuts from all three bands. 8:30pm.

MAY 18

Bindlestiff Family Circus, PINE PLAINS
Bindlestiff Family Variety Arts, Inc., founded by Keith Nelson and Stephanie Monseu in 1995, prides itself on being an integral part of America’s outstanding folk traditions of circus, sideshow, and vaudeville. Come see the show starting at 10 am at the Stissing Center.

Misty Blues, PINE PLAINS
Join the Stissing Center for Misty Blues! This band pays homage to the older blues made popular by the bold and brassy women of its time, while still paying respect to classic male artists of the 20’s, 30’s and 40’s.

Pollinator Day, POUGHKEEPSIE
Join the DLC, Plan Bee Farm Brewery, and Fox Farm Apiary for an afternoon of fun in the outdoors. The DLC will be there offering information on land conservation, prizes & giveaways, and a craft table to build bee hotels and native seed bombs. 4:30 pm.

Jazmine Hayes, of blood and water, make me new to be old again, WASSAIC
Join the Wassaic Project for the premiere of Jazmine Hayes’ of blood and water, make me new to be old again, screened on the side of Maxon Mills after the opening of the 2024 Summer Exhibition, Tall Shadows in Short Order. 8:30 pm – 9 pm.

2024 Summer Exhibition Opening, WASSAIC
Save the date for the opening of the Tall Shadows in Short Order, 2024 Summer Exhibition! The show will feature 30 artists throughout all seven floors of Maxon Mills, with a focus on large, site-specific installations. 4 pm – 6 pm.

A Night at the Museum- CENTERstage Dance Recital 2024, RHINEBECK
Join CENTERstage Dance Studio as they celebrate their 6th annual recital! The Dance Studio is excited to invite you to “A Night at the Museum!” Each piece is inspired by museums and exhibits from around the world. Support their amazing dancers and celebrate all the hard work they have put in this year! 2 pm.

An Evening With Shemekia Copeland, BEACON
Award-winning blues, soul and Americana singer Shemekia Copeland possesses one of the most instantly recognizable and deeply soulful roots music voices of our time. 8:30 pm.

May 19

Le Vent Du Nord, BEACON
The award winning and highly acclaimed band Le Vent du Nord is a leading force in Quebec’s progressive francophone folk movement. 7:30 pm.

Upstate Untitled, PINE PLAINS
Join the Stissing Center for a staged reading of Upstate Untitled. Gloria loves her upstate home of 40 years, but when the pool-digger releases spirits from an ancestral burial ground in the backyard… she has some big decisions to make. 3 pm – 5 pm.

Cottage Courses: Natural Dyes with Kitchen Scraps with Jaime Lyn Kara, PINE PLAINS
The Stissing Center is hosting a Cottage Course instructed by Jamie Lyn Kara. Participants will learn how to turn vegetable scraps from the kitchen into natural color! You will go through the steps of preparing fabrics for dyeing and make a handful of different plant dyes from veggies. 1 pm – 3:30 pm.

MAY 23

Bonsai & Sip, MILLBROOK
Sip wine and learn the fundamental skills and techniques behind the art of bonsai while enjoying a night out with friends! Teachers will introduce core concepts and guide your experience as you pot, prune, and design your very own bonsai tree! 6 pm at the Millbrook Vineyard and Winery.

Latin Dance With Beacon Dance Beat, BEACON
Beacon Dance Beat plays a wide array of Latin rhythmic styles, including Salsa, Merengue, Bachata, Cha-Cha, Rumba, Bolero and MAS. Singles, couples, friends, newcomers – all are welcome. 7 pm.

MAY 24

Nooch’s with Cher Lynn, MILLBROOK
Join Myles Mancuso as he performs with Cher Lynn at Nooch’s Pub. 7 pm – 10 pm.

Jonah Smith Band, BEACON
Smith’s music ranges over his twenty-year career from soul to folk and Americana and he moves effortlessly on stage between keyboards and guitar. 8:30 pm.

MAY 25

Art in the Loft, MILLBROOK
Together with Arts Mid-Hudson, Millbrook Winery is pleased to feature Art in the Loft. The seasonal art exhibit brings our upstairs loft to life and creates a unique opportunity to view the works of talented, regional artists. The artists are selected each Spring by a juried panel.

Faded Rose, BEACON
Faded Rose is an Alternative band from New York, best known for their unique sound and emotionally charged lyrics. 8:30 pm.

MAY 26

The Bob Cats, BEACON
Based in Bob’s old stomping grounds of Woodstock NY, The Bob Cats bring to life the rock ’n’ roll spirit of the Dylan songbook, and the rich history he’s made in this area. 7 pm.

May 31

Hudson Valley Flyers Band, RED HOOK
Join the Red Hook Eat-N-Go for a classic country and honky tonk band for whole family to enjoy. 6 pm – 8 pm.

The Slambovian Circus Of Dreams, BEACON
Explore the depths of Americana “one trippy tune at a time” with New York’s Slambovian Circus of Dreams. 8:30 pm.