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Top 10 Dutchess Events in May

Date Published: April 25, 2024

Spring is in full swing here in Dutchess County, and it is simply beautiful. The flowers are blooming, the leaves are sprouting, and the weather is absolutely gorgeous — as are the views of the Hudson River and the surrounding highlands. There is so much to see and do here in the heart of the Hudson Valley. From outdoor excursions to world-famous cuisine and everything in between, Dutchess has it all.  
Here is a list of the Top 10 Dutchess Events in May, a small sampling of the many fun and memorable experiences that await. You’re going to love it here! Come and explore — and keep that camera handy.  Feel free to share your photos here and tag @DutchessTourism on social media. 

Avocado Toast at Bread Alone, Rhinebeck, one of the Taste of Rhinebeck participants
Avocado Toast at Bread Alone, Rhinebeck, one of the Taste of Rhinebeck participants

Taste of Rhinebeck 

Wednesday, May 1, 5 p.m. in the Village of Rhinebeck 

Taste all the best of what Rhinebeck has to offer at this culinary extravaganza! Sample delicious flavors from the village’s assortment of roughly two dozen fine restaurants, specialty food vendors and spirit shops. There is sure to be something to satisfy every appetite, and you will not go home hungry. Only 450 tickets will be sold for this event, so act fast! Click here to purchase tickets. No tickets will be available at the gate. 

Marist College, Poughkeepsie
Marist College, Poughkeepsie

Marist Fashion's 38th-Annual Silver Needle Runway Show 

Friday, May 3, 7 p.m. at McCann Center, Marist College, Poughkeepsie 

Marist College’s talented senior Fashion Design students take center stage with their amazing garments and creations at this annual event. The title and theme of this year’s 38th annual show, “Interlinked,” is meant to invite people to relinquish their meticulous control over their own lives and embrace the greater idea of humans and everything around them. After all, what is an ocean if not a multitude of singular drops? To purchase tickets, click here.

Pete Seeger's Birthday Celebration: "Sails and Ales" 

Friday, May 3, 7 p.m. at Two Way Brewing, Beacon 

Raise a glass for the late Pete Seeger, the iconic folk singer and environmental activist who was born 105 years ago and whose efforts to clean up the Hudson River more than 50 years ago are still making a difference. Choose from more than a dozen of Two Way Brewing’s craft beers as you join in the revelry. Sing along to sea shanties and traditional folk music. A portion of proceeds from the evening will benefit the organization Pete and Toshi Seeger founded in 1966 to protect the Hudson from pollution. Their ship, the Hudson River Sloop "Clearwater," was launched in 1969 and still serves as "America's Environmental Flagship" to this day. 

Related: The Top 10 Uniquely Dutchess Mother’s Day Experiences includes the Mother’s Day with the Cows event at Harlem Valley Homestead in Wingdale. 

Hudson Valley Theatre Festival 

May 3 – 5 at multiple locations 

The New Deal Creative Arts Center presents this inaugural festival featuring three days of performances throughout the region, including many right here in Dutchess County. Obercreek Farm in Wappingers Falls and the Inn at Bellefield in Hyde Park are among the participating venues in Dutchess. Click here to see the schedule and reserve tickets. Individual tickets and weekend passes are available, so make a weekend out of it! Click here to check out hotels and bed-and-breakfasts as you plan your itinerary. 

The cast of the County Players production of Ragtime The Musical at the Falls Theatre, Wappingers Falls
The County Players cast of "Ragtime: The Musical" at the Falls Theatre, Wappingers Falls (photo by Louisa Vilardi Photography)

County Players Presents "Ragtime: The Musical" 

May 3 – 19 at the Falls Theatre, Wappingers Falls 

The County Players community theatre company has presented hundreds of productions and thrilled thousands of theatregoers since its inception in 1958, and their latest endeavor, “Ragtime: The Musical,” promises to be another smash hit. Based on the novel by E.L. Doctorow, this Tony Award-winning musical depicts an African American family, a Jewish immigrant family, and a wealthy white family who collide in pursuit of the American Dream in turn-of-the-century America. Click here to see the performance schedule and to reserve tickets. 

ArtEast May Open Studio Tour 

May 4 – 5, 11 a.m. – 5 p.m. at multiple locations 

It might be dirty, noisy and chaotic, but this self-guided tour of working art studios will certainly not be dull! The ArtEast May Studios Tour, formerly known as ArtmostNY Open Studio Tour, features a group of working artists in eastern Dutchess who will open their studio doors for two days and allow you to visit while they work. You'll have the opportunity to meet the artists, ask questions and learn about their techniques and inspirations. Click here for the most up-to-date list of artists, their art and their locations and contact information. 

Hudson Valley Marathon 

Sunday, May 5 at the Walkway Over the Hudson, Poughkeepsie 

Enjoy the exhilaration of running a race while admiring the awe-inspiring views of the Hudson River and surrounding countryside at this Boston Marathon qualifier. This second-annual event features races of various lengths for all ages and abilities. The marathon and half marathon courses are both USATF-certified. There is also a 10k race, a 5k race and a 1-mile race. All the races start and finish on the Highland side of the walkway and include trips back and forth across “The World’s Longest Elevated Pedestrian Bridge,” which stretches 1.28 miles across and rises 212 feet above the mighty Hudson. Click here to register and see a course map, and check out the Hudson Valley Marathon Facebook group here.

Eleanor Roosevelt Center at Val Kill, Hyde Park 
Eleanor Roosevelt Center at Val-Kill, Hyde Park

"The First Lady of World War II" 

Saturday, May 11, 2 p.m. at the Eleanor Roosevelt Center at Val-Kill, Hyde Park 

Author Shannon McKenna Schmidt’s book, "The First Lady of World War II: Eleanor Roosevelt's Daring Journey to the Frontlines and Back," examines Eleanor Roosevelt’s role as an important and influential journalist during World War II. Roosevelt’s reporting following her five-week tour of the Pacific theater helped stimulate legislation that led to the famous GI Bill of Rights. Shannon McKenna Schmidt and Kristen Strigel Carter, the Deputy Director of the Franklin D. Roosevelt Museum and Library, present a panel discussion that will explore Eleanor’s courageous endeavors. The conversation will be moderated by Eleanor Roosevelt's great-granddaughter, Anna Eleanor Fierst, who also serves as the Eleanor Roosevelt Center at Val-Kill's Board Chair. Enjoy some light refreshments and stick around for a Q&A session afterward. Click here to reserve tickets and to purchase a signed copy of the book. 

Related: Memorial Day festivities in Hyde Park will once again feature a World War II bivouac on the Great Lawn in front of the Franklin D. Roosevelt Presidential Library and Museum. Learn more here.

Stephan Hengst and Patrick Decker, founders of Big Gay Hudson Valley, on the Walkway Over the Hudson, Poughkeepsie
Stephan Hengst and Patrick Decker, founders of Big Gay Hudson Valley, on the Walkway Over the Hudson, Poughkeepsie

Pride In The Sky 

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

The Walkway Over the Hudson’s brand new LED lighting system will illuminate “The World’s Longest Elevated Pedestrian Bridge” in rainbow light for this first-time Pride celebration. Show your pride with your most “illuminated” attire. Superior Sounds and DJ Ali Gruber host a dance party all night long at the center of the Walkway with featured guests from the LGBTQ+ community. At dusk, an eight-color Pride flag will be paraded from the Dutchess County side of the Walkway over the river to the Ulster County side. Click here to complete the required registration. 

Hudson Valley Graduation Dinner 

Saturday, May 18, 5:30 p.m. at Farquharson Hall, Culinary Institute of America, Hyde Park 

The Culinary Institute of America has a special night planned for all the soon-to-be college graduates in the Hudson Valley! Celebrate your accomplishments alongside fellow graduates as the CIA serves up an amazing three-course meal in beautiful Farquharson Hall. Enjoy passed hors d’oeuvres, live music and an open wine and beer bar. VIP reservations also include a champagne toast, antipasto for the table, and a party favor. Members of the Class of 2024 at all the local colleges — including Marist, Vassar, Bard, and Dutchess Community College — are invited. Click here to reserve tickets. 

Related: Dutchess Tourism's CIA Chef Finder is a free digital passport that helps you find Culinary Institute of America chefs who create world-class cuisine right here in Dutchess County.  

Sports Museum of Dutchess County, Wappingers Falls
Sports Museum of Dutchess County, Wappingers Falls 

Bonus Event 

“Early Hudson Valley Baseball” 

Saturday, May 4, 1 p.m. at the Sports Museum of Dutchess County, Wappingers Falls 

The Sports Museum of Dutchess County will open for the 2024 season and will unveil a renovated baseball room featuring photographs, trophies, and artifacts from local athletes and teams. At 1 p.m., baseball historian Robert Mayer will present a program on “Early Hudson Valley Baseball,” which will feature early baseball artifacts and discussion about local baseball activity, including minor league and semi-pro teams. The family-friendly opening-day festivities will run from 11 a.m. – 4 p.m. and will include music, games for kids, prizes, snacks, raffles, and tours of the museum. Many historic items are on display and many Dutchess County athletes are honored at the SMDC, including Baseball Hall of Famers Eddie Collins, who was born in Millerton, and “Big Dan” Brouthers, who was born in Beekman; and boxer Melio Bettina from Beacon, who was briefly the Light Heavyweight World Champion in 1939. 

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