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Top 10 Dutchess Events in May

Date Published: April 21, 2023

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 taste of the many fun and memorable experiences waiting for you. You’re going to love it here! Come and explore, and keep that camera handy. Feel free to share your photos here.

Be sure to check out the top Memorial Day and Mother's Day events in Dutchess.

Silver Needle Runway Fashion Show

Friday, May 5, 7 p.m. at the McCann Center, Marist College, Poughkeepsie

For nearly 40 years, the Silver Needle Runway Show has highlighted the garments and creations of Marist College’s talented senior Fashion Design students and has cultivated an environment of innovation and encouragement for the next generation of fashion industry icons. The title and theme of this year’s 37th annual event is “[RE]ACTION,” and it is meant to examine today’s social issues and provide a catalyst for change. Click here to purchase tickets. 

Trolley Barn Gallery Poughkeepsie
Trolley Barn Gallery, Poughkeepsie

PKX Reel Exposure Teen Film and Photography Festival

Friday-Sunday, May 5-7 at the Trolley Barn Gallery, Poughkeepsie

Here is a can’t-miss event for any aspiring photographer or filmmaker. This three-day festival showcases innovative and imaginative photographs and short films created by talented teenage artists and offers family-friendly activities and more. A panel discussion on Sunday titled “Breaking into the Business: Insider Info from Film and Media Professionals” will feature actress, producer and director Mary Stuart Masterson; video journalist Nile Clark; director Hezues R.; Jasmine Garvin, alumna of The Art Effect who was recently featured in Peacock’s “Poker Face;” and Magalie Laguerre-Wilkinson, Vice President of News Programming at Nickelodeon and Executive Producer of Nick News. Registration is required for certain events during the festival. Click here for details.

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

New York Cider Week

May 5-14 at multiple Dutchess County locations

The New York Cider Association presents the spring installment of its biannual festival, which celebrates all things cider and those who make it. It’s a great chance to visit local producers, sample their products, enjoy some fun activities and learn about this agricultural staple in the Hudson Valley. Participating Dutchess County cideries include Treasury Cider at Fishkill Farms in Hopewell Junction and Breezy Hill Orchard in Staatsburg, maker of Hudson Valley Farmhouse Cider. For a schedule of Cider Week events, click here.

Treasury Cider is one of the participants on the Dutchess Tourism Taste Finder Craft Beverage Trail, a mobile passport program that serves up perks at a variety of craft beverage tasting rooms and tap houses in Dutchess County. Click here to obtain "The Pass to Fill Your Glass." 

The Hudson Valley's Ultimate Tequila & Mezcal Experience

Saturday, May 6, 1-5 p.m. at 18 North Grill, Fishkill

Boutique Wines, Spirits and Ciders teams up with 18 North Grill to present this event, which is perfect for either the casual tequila drinker or the discerning connoisseur. Interact with representatives from top brands as you taste and explore dozens of samples of tequila, mezcal and sotol. Food bites will be provided, and bottles being tasted will be available for purchase. General admission, VIP and designated driver tickets are available. Click here to reserve yours.

Related: Spring in Dutchess County

ARTmostNY Open Studio Tours

Saturday and Sunday, May 6-7, 11 a.m.-5 p.m. at multiple Dutchess County locations

At the top of the ARTmostNY website reads the following disclaimer: “Warning: Artists at work. Creativity and chaos ahead.” Those same artists are inviting you into their Dutchess County studios to witness that creativity and chaos first-hand during this two-day, self-guided tour. Participating artists include painters, sculptors, photographers and more. Click here to see a list of the artists and their studio locations.

Walkway Over the Hudson Poughkeepsie
Walkway Over the Hudson, Poughkeepsie

Hudson Valley Marathon at the Walkway Over the Hudson

Sunday, May 7 at the Walkway Over the Hudson, Poughkeepsie

Enjoy the exhilaration of running a marathon while admiring the awe-inspiring views of the Hudson River and surrounding countryside at this Boston Marathon qualifier. The day’s events feature 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.

The Walkway is one of the stops on the Dutchess Tourism Zen Finder Outdoor Experience Trail, a free mobile passport program highlighting some of the best hidden-gem trails and fresh-air activities in Dutchess County. Click here to obtain your free Zen Finder pass.

The Bardavon 1869 Opera House Poughkeepsie
The Bardavon 1869 Opera House, Poughkeepsie

The Wallflowers at The Bardavon

Friday, May 12, 7:30 p.m. at the Bardavon 1869 Opera House, Poughkeepsie

As the oldest continuously operating theater in New York State, the Bardavon has a long history of attracting famous entertainers to Poughkeepsie – including John Philip Sousa and Mark Twain back in the day. Add The Wallflowers to that impressive list. The Grammy-winning band fronted by founding singer, songwriter and guitarist Jakob Dylan – Bob Dylan’s son – broke through with their 1996 album “Bringing Down the Horse,” which included the hits “One Headlight” and “6th Avenue Heartache.” The Wallflowers will be joined by Grammy-nominated singer/songwriter Leslie Mendelson. Tickets are selling quickly for this show. Click here to buy yours.

Related: Top Fishing Spots in Dutchess County

“A Fine Line: Graffiti and the Power of Dissent”

Saturday, May 13 at the KuBe Art Center, Beacon

The Ethan Cohen Gallery at the KuBe Arts Center presents this exhibition, which showcases artists who use the power of line and gesture to convey messages of subversion and dissent in their work. It examines the ways artists can use their personal language to speak out against conventions and injustice. The exhibition is scheduled to open May 13. More details to come. Click here for updates.

Maxon Mills Wassaic
Maxon Mills, Wassaic

“Counting the Seconds Between Lightning and Thunder”

Saturday, May 20, 4-6 p.m. at Maxon Mills, Wassaic

The Wassaic Project is proud to announce the opening of its summer exhibition titled “Counting the Seconds Between Lightning and Thunder.” Be sure to visit the one-of-a-kind gallery at Maxon Mills, an old seven-story wooden grain elevator along the railroad tracks that has been repurposed into a magnificent space for contemporary artists to display their creations. The summer exhibition, curated by Eve Biddle, Bowie Zunino, Jeff Bartnett-Winsby and Will Hutnick, will feature the works 40 talented artists and will be on display from May 20 through Sept. 16. The gallery is open Saturdays and Sundays from 12-5 p.m. Along with the exhibition opening, there will also be an Outdoor Paint Jam with Super-Stories for kids and families. Click here for details.

The Wassaic Project is one of the participants on the Dutchess Tourism Inspiration Finder Arts & Culture Trail, a free mobile passport program that unlocks discounts and perks to some of the best cultural institutions, exhibition spaces and performance venues in Dutchess County. Click here for details.

Related: A First-Timer's Guide to Dutchess County

Hudson Valley Graduation Dinner

Saturday, May 20, 5:30-8 p.m. at Farquharson Hall, Culinary Institute of America, Hyde Park

Attention all soon-to-be college graduates in the Hudson Valley: The Culinary Institute of America has a special night planned just for you! 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. Members of the Class of 2023 at all the local colleges – including Bard, Marist, Vassar and Dutchess Community College – are invited. Click here to reserve tickets.

And speaking of the CIA, be sure to check out Dutchess Tourism's new CIA Chef Finder, a free digital passport that helps you find Culinary Institute of America chefs who create world-class cuisine right here in Dutchess County. Click here for details.

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