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Top 10 Events in May

Date Published: April 20, 2022

Spring has finally sprung, and there are so many exciting things to see and do in Dutchess County. Live concerts, car shows and more round out our top 10 May events.

Bannerman Island and Castle Tours Spring
Bannerman Island, Beacon

1. Bannerman Island and Castle Tour 

Starting May 1 at Bannerman Castle, Beacon 

Climb aboard the Estuary Steward tour boat and enjoy a magnificent ride from the Beacon Institute Floating Dock to Bannerman Island, where you can take a guided—or self-guided—walking tour of the island. Visit the famous Bannerman Castle ruins and gardens, and explore the original residence, which is now a museum. Click here for more information and to purchase tickets. 

2. Kentucky Derby Day 

Saturday, May 7 at 12 p.m. at Milea Estate Vineyard, Staatsburg 

Experience all the edge-of-your-seat excitement of the Kentucky Derby at this live viewing party, where the fun will continue long after the race has finished. Sip a Mint Julep—made with Milea’s award-winning 10 Point Gin—as you watch the race unfold on a big-screen television. Dress your best for a chance to win a prize, as two lucky guests will be awarded for their snazzy Derby attire. Click here to make your reservations. 

Bardavon Theater Interior in Poughkeepsie
Bardavon 1869 Opera House, Poughkeepsie

3. Broadway Royalty at Bardavon Gala 

Saturday, May 7, 8 p.m., at Bardavon 1869 Opera House, Poughkeepsie 

Spend an intimate evening with Broadway royalty as six-time Tony, four-time Drama Desk, and two-time Emmy and Grammy Award-winner Audra McDonald performs her signature mix of songs from Broadway, the Great American Songbook, and beyond. Gala guests will enjoy a pre-show cocktail party at Revel 32, featuring a savory selection of celebrity chef David Burke’s signature canapés and hors d’oeuvres; a sweet array of desserts from chef Gwenn Sorensen of the Stone Soup Food Company; and music by Hot Club of Saratoga and Sean Gallagher. For ticket information, click here

4. Rhinebeck Car Shows 

Saturday and Sunday, May 7 and 8, 8 a.m. to 5 p.m., at Dutchess County Fairgrounds, Rhinebeck 

Shift your weekend fun into high gear with two great car shows in one high-octane weekend. Saturday’s Rod and Custom Dust-Off show will be devoted to hot rods, street rods, customs, race cars and compact customs/pickups. Prizes will be awarded in more than 30 categories. Sunday’s show will be for unmodified antique classic vehicles (pre-1997). Prizes will be awarded in 60 classes. The shows will be preceded by a swap meet on Friday, May 6, from noon to 5 p.m. Click here for more information. 

5. Barton Orchards Apple Blossom Festival 

Saturday and Sunday, May 7-8 and 14-15, 11 a.m. to 6 p.m. at Barton Orchards, Poughquag  

Visit Barton Orchards for two consecutive weekends to admire their beautiful display of apple blossoms during this annual festival. There will be plenty for the whole family to enjoy, with hayrides, live music, games, and other entertainment on tap. Enjoy fresh cider, food truck cuisine and spectacular views of the farm. For more information, click here

6. Dia’s Saturday Studio on the Farm Art Workshop 

Saturday, May 14, 10:30 a.m. at Common Ground Farm, Wappingers Falls 

The kids will love this! Join a practicing artist for a free, outdoor workshop full of art, exploration, and creativity. Dia’s Saturday Studio is a family-friendly program suitable for ages 5 and up. Space is limited, and reservations are required (reservations open May 6). For more information and to register, click here

Richard B. Fisher Center for the Performing Arts at Bard College, Annandale-on-Hudson 
Richard B. Fisher Center for the Performing Arts at Bard College, Annandale-on-Hudson 

7. The Bard Conservatory Orchestra 

Saturday, May 14, 8 p.m. at Richard B. Fisher Center for the Performing Arts at Bard College, Annandale-on-Hudson   

Music director Leon Botstein and the Bard Conservatory Orchestra present their final concert of the academic year. The program will include performances of Franz Liszt’s “Mazeppa – Symphonic Tone Poem No. 6,” with Andres Rivas serving as conductor; Maurice Ravel’s “Schéhérezade,” featuring the vocal stylings of mezzo soprano Hailey McAvoy (a VAP Concerto Competition winner), and James Bagwell as conductor; and Brahms’ “Symphony No. 2,” with Leon Botstein as conductor. Proof of vaccination will be required for admittance, and masks must be worn. For more information and to purchase tickets, click here

8. Samuel Clemens: Tales of Mark Twain 

Saturday, May 21, 7 p.m., and Sunday, May 22, 2 p.m. at The Stissing Center, Pine Plains 

This solo show, written and performed by Joe Baer, takes its audience on a nostalgic stroll back in time in portraying the famous author’s life, from his roots in rural Missouri through his rise to international acclaim. Baer uses Twain’s own words to weave an historical tapestry while recalling the iconic storyteller’s many triumphs and tribulations, paying special attention to his crusades against many of America’s social issues of the day, including racism, class barriers and access to education. To purchase tickets, click here

9. Music on the Elmendorph Green 

Saturday, May 28, 5 p.m. at Elmendorph Inn, Red Hook 

Good news, live music fans! The first event on the annual summer concert series’ 2022 calendar is a free performance by the Eugene Tyler Band, a bluegrass trio whose third full-length album, Thanks Cats, was released in 2021. Bring a lawn chair or a picnic blanket and get ready for a fun, high-energy outdoor show by three native New Yorkers. For more information, click here

Plan Bee Farm Brewery Barn Beer in Taproom
Plan Bee Farm Brewery, Poughkeepsie

10. Misto food truck visits Plan Bee Farm Brewery 

Saturday, May 28, noon to 7 p.m., at Plan Bee Farm Brewery, Poughkeepsie  

Misto’s husband-and-wife team of Wilson and Nadia Costa cooks up a savory, gluten-free fusion of Brazilian and Ukranian flavors using hyperlocal ingredients. Wash it all down with one of Plan Bee’s tasty farmhouse beers. There will be designated areas to sit and eat; or bring your own lawn chairs and picnic blankets. No tickets required. For more information, click here.

Ready for more events? To visit our online events calendar, click here. Stay tuned for our guide to Mother's Day events and activities!

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