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Top 10 Dutchess Events in May

Date Published: April 27, 2026

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 @DestinationDutchess on social media. 

Hudson River Sloop Clearwater
Hudson River Sloop "Clearwater"

Pete Seeger Birthday Celebration

Saturday, May 2, 6 p.m., at the Towne Crier Cafe, Beacon 

On the eve of what would have been the 106th birthday of folk music icon and longtime Beacon resident Pete Seeger, the famous Towne Crier Cafe presents a special concert featuring two musicians who had joined him on stage on more than one occasion. Steve Kirkman and Jake Bernz’s new project, “National Anthems,” will feature songs in the folk vein and will also bring forward the traditions of songs of social conscience. There will also be a rare solo set from David Bernz, who was Pete Seeger’s Musical Producer for over two decades, winning two Grammy Awards. This concert on the Towne Crier's Salon Stage is free with dinner. Pete and his wife, Toshi, were longtime environmental activists and advocated for the cleanup of the Hudson River in the 1960s after decades of industrial pollution. Their ship, the Hudson River Sloop "Clearwater," was launched in 1969 and still serves as "America's Environmental Flagship" to this day. 


West Point Band
West Point Band

West Point Band: America 250

Saturday, May 2, 7 p.m., at the James & Betty Hall Theatre, Dutchess Community College, Poughkeepsie

The West Point Band presents a special series of concerts in celebration of America’s 250th anniversary. These performances will honor the rich musical heritage of America and music’s connection to the American story. Join the West Point Band as they bring inspiring music to audiences throughout the Hudson Valley and beyond in commemoration of this year's semiquincentennial. This free concert at Dutchess Community College is open to all.


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.


ArtEast May Open Studio Tour 

Saturday and Sunday, May 2 and 3, 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 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 a list of artists, their art, and their locations and contact information. 


Treasury Cider, Fishkill Farms, Hopewell Junction
Treasury Cider at Fishkill Farms, Hopewell Junction

New York State Cider Week

May 2–10 at multiple locations

Raise a glass and toast to New York State's burgeoning cider industry, which is bolstered by numerous producers right here in Dutchess County. Check out these cider-themed events here in Dutchess and taste the quality of our local products:

• Apple Blossom Festival & Vendor Market (at Fishkill Farms, Hopewell Junction), Sunday, May 3, 11 a.m.

• Core & Craft: Apples in New York from Orchard to Glass (at Denning's Point Distillery, Beacon), Friday, May 8, 7 p.m.

• Sip n' Stretch Yoga (at Treasury Cider, Fishkill Farms, Hopewell Junction), Saturday, May 9, 11 a.m.

• Flower Vase Pottery & Cider Sipping (at Treasury Cider, Fishkill Farms, Hopewell Junction), Saturday, May 9, 1 p.m.


Related content: Spend Memorial Day Weekend in Dutchess


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

Taste of Rhinebeck 

Wednesday, May 6, 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. For your shopping enjoyment, you're welcome to browse select shops and retailers. Click here to purchase tickets in advance and save (tickets will not be sold at the gate). 


Lindsey Danis: "(Out) On the Road: The Radical Joy of Queer Travel"

Friday, May 8, 6 p.m., at Oblong Books, Rhinebeck

"Stop hiding. Start traveling on your terms." That is the message author Lindsey Danis is promoting in the new book "(Out) On the Road: The Radical Joy of Queer Travel." Queer people spend around $100 billion annually on travel and are twice as likely as the general population to hold a passport, but despite lavish spending, queer travelers are often underserved. Weaving Danis' personal experiences with data and interviews, "(Out) On the Road" empowers LGBTQ+ travelers to face their fears, expand their comfort zones, find community, and thrive on the road. Advance registration is required for this free event at Oblong Books in Rhinebeck. Be sure to pre-order your copy of "(Out) On the Road."


Marist College, Poughkeepsie
Marist University, Poughkeepsie

Marist University's 40th-Annual Silver Needle Runway Fashion Show 

Friday, May 8, 7 p.m., at  the McCann Center, Marist University, Poughkeepsie 

Marist University'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 40th-annual show is "BURN," and it represents looking beyond the burdens of burnout and turning toward your burning passions. Inspired by how the world has changed with the introduction of different technologies, "BURN" is a symbol of Marist Fashion students pursuing their art through creativity and individuality. To purchase tickets, click here.


Clover Brooke Farm, Hyde Park

Dutchess County Sheep and Wool Growers Association Sheep & Wool Growers Farm Tour 

Saturday, May 9, 10 a.m.–4 p.m., at multiple locations 

This self-guided tour offers visitors a unique opportunity to explore local farms, meet farmers, and learn about raising sheep and fiber production. Each participating farm will showcase a variety of activities and demonstrations. Visitors will also have the chance to purchase a wide range of farm-produced goods, including yarn, wool products, handmade crafts, and other locally produced items. As part of the event, visitors who sign in will be entered into a special raffle featuring a prize basket filled with farm-produced items from each of the participating farms — offering a unique collection of local products. Participating farms include Clover Brooke Farm (Hyde Park); Patchwork Pastures (Hyde Park); Point of View Farm (Stanfordville); Stony Kill Farm (Wappingers Falls); Springhill Farm (Rhinebeck); Anchorage Farm (Saugerties); Nobletown Fiber Works (Hillsdale).


Germania of Poughkeepsie. Photo by Karen-Rose
Germania of Poughkeepsie (Photo by Karen-Rose)

Maifest 2026

Friday, Saturday and Sunday, May 15, 16 and 17, at Germania of Poughkeepsie

Celebrate springtime at this traditional German festival featuring three days of authentic German food and beer along with live music and dancing performances, games, childrens activities and local vendors. Enjoy Bavarian-style sausages and desserts, pretzels, sauerkraut, potato salad and so much more. Formed in 1850, Germania of Poughkeepsie is the oldest German singing society in New York outside of New York City.


Pride in the Sky, Walkway Over the Hudson, Poughkeepsie (photo by Tanner Townsend)
Pride in the Sky, Walkway Over the Hudson, Poughkeepsie (photo by Tanner Townsend)

Pride In The Sky 

Saturday, May 30, 3–10 p.m., at the Walkway Over the Hudson, Poughkeepsie 

It's the perfect way to kick off Pride Season in the Hudson Valley! This third-annual event has welcomed thousands of participants and hundreds of volunteers to the Walkway Over the Hudson each of the last two years. This year's festival is sure to be another blockbuster event, featuring Queer Families Festival on the Poughkeepsie end of the Walkway from 3–6 p.m., followed by the Pride and Trans flag processions across the Walkway at 6:45 p.m. and dancing and drag under the stars from 7–10 p.m.


Bonus Event

East Fishkill Civil War Weekend

Saturday and Sunday, May 2 and 3, at the Brinckerhoff House Historic Site, Hopewell Junction

The East Fishkill Historical Society hosts this fifth-annual event featuring living history demonstrations. Witness tactics and weapons demonstrations, including muskets and a cannon. Learn about camp cooking, listen to period music and see historic artifacts. It's the perfect opportunity to tour the Brinckerhoff House Historic Site's grounds, farmhouse, ice house, school house, barn and blacksmith shop. On Saturday at 1 p.m., be sure to catch  the premier presentation of “unCivil Spies” presented by History At Play LLC, which tells the story of Elizabeth Van Lew, who was a spy for the Union Army.


Hudson Valley Marathon 

Sunday, May 3 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 the surrounding countryside at this Boston Marathon qualifier. This 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 Over the Hudson 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.

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