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Top 10 Dutchess Events in June

Date Published: May 18, 2023

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.

And there are plenty of Pride Month and Juneteenth events coming up in Dutchess, too!

Franklin D Roosevelt Presidential Library and Museum Hyde Park
Franklin D. Roosevelt Presidential Library and Museum, Hyde Park

“Black Americans, Civil Rights and the Roosevelts, 1932-1962” 

Opens Saturday, June 3, 9 a.m. at the Franklin D. Roosevelt Presidential Library and Museum, Hyde Park 

The Franklin D. Roosevelt Presidential Library and Museum unveils a special new exhibition titled "Black Americans, Civil Rights and the Roosevelts, 1932-1962." The exhibit, which opens on June 3 and will be on display through 2024, examines the political evolution of Franklin and Eleanor Roosevelt regarding racial justice and highlights the historical voices of Black community leaders, wartime service members and ordinary citizens who pushed the Roosevelt administration for progress. Visitors will see documents and artifacts — many on display for the first time — from the Roosevelt Library’s expansive holdings and from private collections. During the second of his four terms as President, Roosevelt established the first Presidential Library to preserve and provide public access to all his papers and memorabilia. He believed the American people were entitled to an open look at how their government was working. The Library and Museum is open seven days a week, from 9 a.m. to 6 p.m. April through October and from 9 a.m. to 5 p.m. November through March. The museum will be open from 9 a.m. to 3 p.m. on June 3. Click here to purchase tickets online. 

Mount Gulian Historic Site Beacon
Mount Gulian Historic Site, Beacon

Dinner and Conversation with President James Madison 

Saturday, June 3, 4:30-9 p.m. at the Mount Gulian Historic Site, Beacon 

Join former President James Madison (portrayed by a highly skilled actor from the American Historical Theatre) for a historically themed dinner and spirited conversation at the Mount Gulian Historic Site. Meet the “Father of the Constitution” and learn the process through which our nation’s founding principles took shape. Enjoy cocktails on the lawn overlooking the Hudson River, a four-course dinner served in the 18th century Dutch barn and live and silent auctions. The deadline to purchase tickets is May 24. Click here for more information. A visit to Mount Gulian gives you access to a treasure chest of historical artifacts and information, beginning with the Indigenous people who inhabited the property thousands of years ago and continuing with the Dutch settlement of the Hudson Valley and the construction of the Verplanck family homestead around 1730. This homestead and its many extraordinary residents through the years played pivotal roles in the American Revolution, the Civil War and the fight to end slavery. Click here to learn more about Mount Gulian’s fascinating history. 

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

Immigrants and the Creation of American Gardening 

Sunday, June 4, 2 p.m. at the Wallace Visitor Center, Hyde Park 

From the colonial period through to modern times, immigrants have continued to introduce new plants and practices — both beneficial and problematic — to American landscapes. At Bellefield’s Annual Design Lecture, renowned horticulturist and landscape designer Wambui Ippolito examines various landscape histories and demonstrates how the American terrain has been permanently altered in a short period of time. She hopes the audience will leave with a new understanding of and appreciation for land management and gardening practices. Ippolito is a graduate of the New York Botanical Garden’s School of Professional Horticulture. She is the founder of the BIPOC Hort Group, an organization with membership from the African American, Asian, African, Latin American and Caribbean public and private professional ornamental horticulture community. The lecture at the Wallace Center will be followed by a reception in the Beatrix Farrand Garden. Located on the grounds of the Home of Franklin D. Roosevelt National Historic Site, the garden was created in 1912 by famous landscape designer Beatrix Farrand. To purchase tickets, click here.

Bernie Williams Millbrook Vineyards and Winery
Bernie Williams (photo courtesy of Millbrook Vineyards and Winery)

A Night of Jazz with Bernie Williams 

Saturday, June 17, 7 p.m. at Millbrook Vineyards and Winery, Millbrook 

Former New York Yankees all-star center fielder Bernie Williams — who, in addition to his skills on the baseball diamond, is also an extraordinary musician and wine aficionado — returns to Millbrook Vineyards and Winery for a special concert. Join the four-time World Series champion and acclaimed guitarist, whose unique blend of music mixes jazz, rock and a taste of the tropical sounds of his Puerto Rican heritage. Williams' first album, "The Journey Within," was released in 2003 and reached No. 3 on the Billboard Contemporary Jazz chart. Be sure to sample some of "Bernie's Blend," a combination of Cabernet and Merlot with a touch of Zinfandel for spiciness, which Millbrook Winery introduced to mark the launch of the 2022 jazz season. Only 50 cases were made. "Bernie's Blend" will be available to taste and to purchase at the concert. Food trucks will be on site, and wine will be available by the glass or bottle. Click here to purchase tickets.  

And to hear Bernie Williams talk about Bernie's Blend on NBC's "New York Live", click here.

Millbrook Vineyards and Winery is one of the stops on the Dutchess Tourism Taste Finder Craft Beverage Trail, which unlocks perks and offers at tasting rooms and tap houses throughout the county. Click here to obtain “The Pass to Fill Your Glass.” 

Howland Cultural Center Beacon
Howland Cultural Center, Beacon

Beacon LitFest 

Saturday and Sunday, June 17-18 at the Howland Cultural Center, Beacon 

Calling all wordsmiths! Beacon’s inaugural literary festival will be a weekend-long collaboration of talented and renowned storytellers at the Howland Cultural Center, “The Jewel of Beacon” and a local hub of creative energy. On Day 1 of the festival, nationally and internationally recognized writers, poets and playwrights will share insight and advice and provide updates on their new works. Participants will include Ginger Strand, Jamie Price, Ph.D., and Donna Minkowitz in nonfiction, Patricia Spears Jones, Indran Amirthanayagam and Martine Bellen in poetry, Charlotte Meehan and Nigel Gearing in drama, and Laura Sims and Danielle Trussoni in fiction, along with special guest Will Shortz, puzzle master for NPR and the New York Times. Day 2 of the festival will include three workshops: “Live Writing-Poetry" with poet Ruth Danon, “Is it Memoir? Is it Fiction?” with writer Ken Foster, and “From Stage to Page” with dramaturg Shane Bly Killoran. To purchase tickets for either day of LitFest, click here.

The Howland Cultural Center is one of the stops on the Dutchess Tourism Inspiration Finder Arts & Culture Trail, 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. 

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

Bard SummerScape 

June 23-Aug. 13 at the Fisher Center, Bard College, Annandale-on-Hudson 

Get ready for eight action-packed weeks of performing arts at Bard College’s 20th annual SummerScape! This year’s schedule includes theatrical performances of “Illinois,” which is the product of the brilliant collaboration between three artists (Tony Award-winner Justin Peck, composer Sufjan Stevens and Pulitzer Prize-winning playwright Jackie Sibblies Drury) to create spectacular display of storytelling, dance, theater and music based on Stevens’ 2005 album titled “Illinois.” Also on tap are performances of the French opera “Henri VIII” by Camille Saint-Saens. Directed by Jean-Romain Vesperini, this production stars Alfred Walker (bass-baritone) as Henri VIII and Lindsay Ammann (mezzo-soprano) as Anne Boleyn. The Spiegeltent, meanwhile, will keep the party hopping all summer long with live music performances, drinks and dancing. SummerScape also includes the 33rd incarnation of the Bard Music Festival, which will explore the life and work of Ralph Vaughan Williams, one of the greatest symphonists of the 20th century. Click here to see the full lineup of SummerScape events.  

The Fisher Center is also a stop on the Dutchess Tourism Inspiration Finder Arts & Culture Trail.

Related: CIA Chef Finder Food Lovers Trail 

Hudson Valley Food Truck Festival 

Saturday, June 24, 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.

Walkway Over the Hudson Poughkeepsie
Walkway Over the Hudson, Poughkeepsie

Discover Hudson Valley Bicycle Ride 

Sunday, June 25, 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. Click here for details.  

For those arriving by train, be sure to check out the National Park Service’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. 

The Walkway is one of the checkpoints on the Dutchess Tourism Zen Finder Outdoor Experience Trail, a free curated itinerary featuring some of the best hidden-gem trails, fresh-air activities and captivating views. Win prizes by checking in at locations throughout the county. Click here to get your pass and start exploring!  

Related: Where to Find Great Pizza in Dutchess County

Mikhail Baryshnikov at 75 

Sunday, June 25, 2 p.m. at Kaatsbaan Cultural Park, Tivoli 

Celebrate the 75th birthday of iconic dancer, choreographer and actor Mikhail Baryshnikov with a festive day of music co-presented by the Baryshnikov Art Center and Kaatsbaan Cultural Park on Kaatsbaan’s picturesque 153-acre campus on the banks of the Hudson River. It is sure to be a celebration befitting such a talented and influential artist as Baryshnikov, who, of course, is widely considered one of the greatest dancers of this — or any — generation. The afternoon’s program will feature performances by American avant-garde artist, composer and musician Laurie Anderson; Canadian jazz pianist and singer Diana Krall; Russian-born American singer, songwriter and pianist Regina Spektor; and North America's preeminent practitioner of Japanese shinobue and taiko drum, Kaoru Watanabe. There will also be a musical performance by choreographer Mark Morris, along with a special appearance by actress Anna Baryshnikov. Click here to reserve tickets.  

Related: Top Fishing Spots in Dutchess County 

Powerhouse Theater at Vassar College 

June 25-July 30 at multiple locations at Vassar College, Poughkeepsie 

The 37th Powerhouse Theater season at Vassar College features another superb lineup of imaginative and insightful plays, workshops and works-in-progress. Musical workshops include "Skyward: An Endling Elegy" (July 7-9) and "We Start in Manhattan: A New Queer Musical"(July 14-15). Play workshops include "Call Fosse at the Minskoff" (July 20-23), "The Chevalier" (July 22) and "Behind the Attic Wall" (July 28-30). Readings include “Canaan Unremembered” (June 25), “birthday birthday birthday” (June 30), "Culture Shock" (July 1) and “Useful People” (July 2). The Powerhouse Theater Training Company will present “A Midsummer Night’s Dream” (July 14-16), “Macbeth” (July 21-23), “Real Human Beings” (July 6, 13, 20, 27) and "Once in a Hundred Years (July 23-24), followed by the Training Company’s New Works Play Festival (July 29). All musical workshop and play workshop tickets are $30, while readings and Training Program performances are free, no ticket required. To purchase tickets, click here. There will also be a special event on July 16 in the Frances Lehman Loeb Art Center titled "Performing Art," in which local performing artists ages 18 and older are invited to contribute to a performance piece inspired by the art currently on view at the Loeb. For more information and to join the cast, click here.

Old Rhinebeck Aerodrome Red Hook
Old Rhinebeck Aerodrome, Red Hook

Bonus Event: 

Air Shows at the Old Rhinebeck Aerodrome 

Saturdays and Sundays, June 17-Oct. 15, 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.

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