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Top 10 Dutchess Events in June

Date Published: May 29, 2024

June is a wonderful time to visit New York’s Hudson Valley, and whether you’re planning a day trip, a weekend getaway or a longer excursion, there is so much to see and do here in Dutchess County. 

Relax and recharge as you bask in the natural beauty and splendor of the Hudson River and surrounding mountains. Witness the past come to life at our many historic sites, including Gilded Age mansions and colonial-era homesteads. Let your creative spirit soar at our plenitude of performance venues and art galleries. Indulge in a diverse array of culinary flavors from all over the globe at our world-class restaurants. 

There really is something for everyone here in Dutchess County, where there is an adventure waiting around every corner. 

Here is a list of the Top 10 Dutchess Events in June — a mere fraction of the county’s many can’t-miss attractions and experiences. Have fun — and be sure to keep that camera handy! Feel free to share your photos here.

Interior picture of the bar at The Vinyl Room, Beacon
The Vinyl Room, Beacon

Eat Drink Beacon Food Crawl

Saturday, June 1, 3–7 p.m. on Main Street, Beacon

Celebrate all the best of what Beacon's vibrant and trendy Main Street has to offer. Sample delicious foods and refreshing beverages from many of Beacon's finest restaurants and tap rooms. Check out the unique offerings from some of Beacon's most popular boutiques and businesses. Tickets are selling quickly and last year's event was sold out, so don't wait! Click here to purchase your tickets. Have your tickets ready and check in at one of three checkpoints to receive a wristband and a map: the Beacon Chamber of Commerce (146 Wolcott Avenue) from 2–4 p.m.; Happy Valley Arcade Bar (296 Main Street) from 2–7 p.m.; or The Leaf (498 Main Street) from 2–4 p.m.

Instructor guided a student aiming a shotgun at the Orvis Sandanona Shooting Grounds, Millbrook
Orvis Sandanona Shooting Grounds, Millbrook

Orvis Shotgun Classic Shooting Clinic

Friday and Saturday, June 7 and 8 at the Orvis Sandanona Shooting Grounds, Millbrook

Host Paula Moore of Orvis Sandanona and a team of internationally esteemed guest instructors will lead this two-day clinic, which offers an opportunity for skilled shooters to refine their technique. Participants will have access to these experts' tips, tricks, and adjustments that will enhance their success both on the clays course and in the field. Moore is a nine-time National Sporting Clays Association All-American, a five-time member of NSCA Team USA, a three-time World Side-By-Side champion, and a six-time New York State Sporting Clays champion. In 2020, she became the first female Chief Shooting Instructor at the Orvis Sandanona Shooting Grounds, the oldest permitted shotgun club in the United States. To see a list of the guest instructors who will be joining Moore, and to register for the clinic, click here.

Howland Cultural Center Beacon
Howland Cultural Center, Beacon

Beacon LitFest 

June 7–9 at the Howland Cultural Center, Beacon 

Calling all wordsmiths! Beacon’s second-annual literary festival will be a three-day collaboration of talented and renowned storytellers at the Howland Cultural Center, “The Jewel of Beacon” and a local hub of creative energy. Enjoy readings, performances, workshops, and much more. Come face-to-face with award winning writers and hear some fresh, new literary voices. Click here to see the festival schedule and to purchase tickets.

Related: Celebrate Pride Month in Dutchess County with a host of fun events, including "Cabaret on the Hudson: A Musical Evening at Edgewater" at the riverfront estate once owned by writer Gore Vidal. Click here for a guide to all the Pride celebrations in Dutchess.

Beacon Sloop Club Strawberry Festival

Sunday, June 9, 12–5 p.m. at Pete and Toshi Seeger Riverfront Park, Beacon

The strawberries are ripe for the picking here in the Hudson Valley, and to celebrate, the Beacon Sloop Club is hosting its beloved annual Strawberry Festival. Grab your forks and come on over for a fun, family-friendly event on the shores of the majestic Hudson River. Enjoy all sorts of strawberry treats while you listen to live music performances and shop from local vendors. The Beacon Sloop Club’s boat, the Woody Guthrie, will be taking guests on free sails from the Beacon Harbor. The public may sign up for an afternoon sail to relax and experience the beauty, power and grandeur of the Hudson (weather permitting). Sign up at the Beacon Sloop Club table starting at noon. To learn more, click here.

Bloodlines Interwoven: A Festival of Art & Diaspora

June 10–16 at Kaatsbaan Cultural Park, Tivoli 

Baryshnikov Arts presents this inaugural week-long musical and cultural festival at Kaatsbaan’s scenic 153-acre campus on the banks of the Hudson River. Enjoy artist talks, evening-length concerts, late-evening fireside music, curated storytelling and discussion sessions and more. All will feature a multicultural collective of world-class musicians led by Festival Artistic Director Kaoru Watanabe, a renowned instrumentalist and composer. Click here to see the festival schedule and to purchase tickets.

Old Rhinebeck Aerodrome Red Hook
Old Rhinebeck Aerodrome, Red Hook

Air Shows at the Old Rhinebeck Aerodrome 

Saturdays and Sundays, June 15–Oct. 20, 2 p.m. at the Old Rhinebeck Aerodrome, Red Hook 

Up, up and away! The Aerodrome is set to begin a new season of high-flying action with antique air shows every Saturday and Sunday! The Saturday "History of Flight" program highlights the Pioneer Era before World War I and the Golden Age of Aviation in the 1920s and 30s. The Sunday air show is the World War I dog-fight spectacular, with a hero or heroine, the villainous Black Baron of Rhinebeck, scenery, pyrotechnics and a World War I tank, along with many antique automobiles. There are usually between 15 and 20 flyable aircraft for each show, including a 1909 Bleriot, a Fokker DR-1 Triplane and a precise replica of the Spirit of St. Louis. Open-cockpit biplane rides — which offer stunning views of the Hudson River and the surrounding highlands — are available before and after the air shows from 10 a.m. until twilight. Gates open at 10 a.m., which gives you plenty of time to check out the Aerodrome’s museum and grab a bite to eat at the snack stand. To purchase tickets, or to book your own biplane ride, click here. Head to the Aerodrome on select Wednesdays this summer for Flight Nights featuring live music, food trucks, biplane rides and family fun. 

Related: Start celebrating America's 250th birthday early at the RevCon 2024 Revolutionary War Reenactment and History Fair at the FDR Library and Museum on June 8. Click here for details.

Hudson Valley Food Truck Festival 

Saturday, June 15, 11 a.m.–5 p.m. at Barton Orchards, Poughquag 

Bring your family — and your appetite — to Barton Orchards for the Hudson Valley Food Truck Festival, the ultimate foodie extravaganza! Indulge in all the sweet and savory flavors of the Hudson Valley as you dig into delectable dishes from a wide variety of food trucks and vendors. Enjoy live music as you check out the farm market, beer garden, dog park, petting zoo and plenty of fun activities. Click here for ticket information. Be sure to swing by The Apple Core, Barton Orchards’ year-round farm market on Noxon Road in Poughkeepsie, which offers fresh baked goods, fudge, produce, maple syrup, milk, meat, jarred products and much more.

Fisher Center Bard College Annandale on Hudson
Fisher Center, Bard College, Annandale-on-Hudson

Bard SummerScape and Spiegeltent 

June 20–Aug. 18 at the Fisher Center, Bard College, Annandale-on-Hudson 

Get ready for two action-packed months of performing arts at Bard College’s 21st-annual SummerScape! This summer’s highlights include performances of James Joyce's "Ulysses" by Elevator Repair Service; Urban Bush Women's 40th anniversary celebration featuring "SCAT!," a new dance-driven jazz club spectacular; and a new opera by Giacomo Meyerbeer titled "Le Prophete," which features the American Symphony Orchestra conducted by Leon Botstein. The Spiegeltent, meanwhile, will keep the party hopping all summer long with live music performances, drinks and dancing. Spiegeltent performers this summer will include Larry Owens, Susanne Bartsch, Sandra Bernhard, Nona Hendryx and Ari Shapiro. Click here to see the full lineup of SummerScape and Spiegeltent events and to purchase tickets.

Related: The Dutchess Tourism Inspiration Finder Arts & Culture Trail is a free mobile passport program offering discounts at some of the best cultural institutions, exhibition spaces and performance venues in the county. Click here to obtain your pass and enjoy access to a curated itinerary of world-class arts attractions. 

Powerhouse Theater at Vassar College 

June 21–July 28 at multiple locations at Vassar College, Poughkeepsie 

The 38th Powerhouse Theater season at Vassar College features another superb lineup of imaginative and insightful plays, workshops and works-in-progress. This season’s highlights include the new comedy “Messy White Gays;” the lesbian spy thriller musical “Absolute Zero;” “Shanghai Sonatas,” the musical based on the memoirs of Jewish refugee musicians who escaped Nazi Germany and found refuge in Shanghai; and episodes-in-progress of the Webby Award-honored podcast “A Simple Herstory.” Liz Dahmen returns for the second installment of "Performing Art" at the Frances Lehman Loeb Art Center. Vassar also welcomes a group of young actors, directors, and writers as members of the Powerhouse Theater Training Company. These emerging artists will present a slate of free theater, including Shakespeare’s "Twelfth Night" and "The Taming of the Shrew." Broadway hits that got their start at Powerhouse include "Hamilton" and "Hadestown." Perhaps one of this year's productions will be the next big smash! To see the season schedule and to purchase tickets, click here. 

Walkway Over the Hudson Poughkeepsie
Walkway Over the Hudson, Poughkeepsie

Discover Hudson Valley Bicycle Ride 

Rescheduled from June 23 to July 13, 7:30 a.m., all routes begin and end in Waryas Park, Poughkeepsie 

With six different routes ranging in length from the family-friendly 15-miler to the challenging 100-miler, the Discover Hudson Valley Ride is the perfect opportunity for cyclists of all abilities to saddle up and enjoy a scenic bike ride among the region’s bucolic countryside. Centered around the Walkway Over the Hudson, all routes begin and end at Victor C. Waryas Park, which is right next to the Poughkeepsie train station. Plus, new for this year, the Walkway Over the Hudson and the Hudson Valley Rail Trail will be open to Discover Hudson riders only! Click here for details.  

For those arriving by train, be sure to check out the Hudson River Valley National Heritage Area’s free Hudson River Train Tour app. Part travel guide, part audio tour, this app uses location services to describe the points of interest you’re approaching along your train ride in real time. It works on the Metro-North Hudson Line between New York City and Poughkeepsie and on Amtrak between New York City and Albany. 

Related: This year's Juneteenth commemoration in Poughkeepsie includes the "Navigating the Underground Railroad in the Hudson Valley" lecture at the Walkway Over the Hudson on June 2. Click here for details on Juneteenth celebrations throughout Dutchess County.

Bonus event:

Staatsburgh Photographic Scavenger Hunt 

Now through Oct. 31 at Staatsburgh State Historic Site, Staatsburg 

Here’s a fun activity for adults and kids alike. Explore the expansive grounds surrounding the Mills Mansion at Staatsburgh State Historic Site, complete 10 specific tasks and win a free ice cream cone from Stewart’s Shops! It’s a great way to learn more about this opulent Gilded Age estate on the banks of the Hudson as you enjoy the natural beauty and breathtaking views of the river and the Catskill Mountains. You’ll need a camera phone to complete the scavenger hunt. Click here to download the instructions and get started. The knowledgeable staff at Staatsburgh does a terrific job with its themed tours of the 79-room mansion, which is still decorated with the family’s original furniture and artwork. Among the most popular tours are the “Tales of the Titanic” tour — Ogden and Ruth Mills had tickets for the Titanic’s return voyage, which, of course, never happened — and the “Gilded Age Scandals” tour — Ogden and Ruth were upstanding citizens, but some of their Gilded Age friends and neighbors certainly were not! There will also be a special tour to commemorate the Juneteenth holiday; "Defying Expectations: How Local Black Women of the Gilded Age Reshaped Black Education and Literacy into the 20th Century" is set for June 15 at 2 p.m. Click here to schedule a tour. 

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