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Enjoy Outdoor Concerts in Dutchess County

Date Published: May 22, 2023

Outdoor music performances come in all shapes and sizes: fist-pumping rock and roll, toe-tapping jazz, boot-scootin' country music, old-fashioned jug band music — and everything in between. With dozens of venues throughout Dutchess County hosting all types of concerts this spring, summer and fall, there will certainly be plenty of opportunities to get out and see a great show and enjoy the fresh air and spectacular views of New York’s Hudson Valley.

Here are some of the highlights (check back regularly, as more events are sure to be added): 

American Ballet Theatre at Kaatsbaan Cultural Park Spring Festival 2021 Tivoli photo by Quinn Wharton
American Ballet Theatre at Kaatsbaan Spring Festival 2021 (photo by Quinn Wharton)

Kaatsbaan Spring Festival 

June 2-18 at Kaatsbaan Cultural Park, Tivoli 

Kaatsbaan’s scenic 153-acre campus on the Hudson River is an awe-inspiring environment in which creative minds of all types can thrive and flourish. This year’s Spring Festival is a three-week celebration of dance, music, film, nature and visual arts and features both indoor and outdoor performances and events. The Opening Reception on June 2 features an art exhibition — displayed both in Kaatsbaan’s art gallery and throughout the grounds — curated by Hilary Greene. The ensuing three weeks will feature performances by the Limón Dance Company and the American Ballet Theatre Studio Company (June 3 and 4), famed string quartet Ethel (June 9), Grammy-nominated violinist and composer Curtis J. Stewart and Ethel (June 10), and the Trisha Brown Dance Company, the New Jersey Ballet and Roderick George’s company, kNoname Artist (June 11). Kaatsbaan’s Culinary Conversation series continues June 11 with "Storing and Saving: The Foundation of Great Cooking," with Tamar Adler, author of “The Everlasting Meal Cookbook” and a contributing editor at Vogue Magazine. There will be a screening on June 16 of “Move Me,” a HUDSY original series showcasing the most talented dancers, choreographers and performers in the Hudson Valley. Enjoy a 90-minute guided nature walk through Kaatsbaan’s grounds led by Wild Gather co-founders Lauren Giambrone and Mandana Boushee on June 17. The festival culminates with performances on June 17 and 18 of “WE,” an evening-length collaboration between Emily Coates and Emmanuèle Phuon, both former dancers of Mikhail Baryshnikov’s and Yvonne Rainer’s companies. To purchase tickets to any or all of these magnificent productions, click here.

Bernie Williams photo courtesy of 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 

In addition to being an all-time great in the hearts of New York Yankees baseball fans, former all-star center fielder Bernie Williams is also an extraordinary musician and wine aficionado — and he is returning to Millbrook Vineyards and Winery for a 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. "Bernie's Blend," a unique combination of Cabernet and Merlot with a touch of Zinfandel for spiciness, 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. To purchase tickets, click here. 

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.”

Millerton's "Celebrate Summer" Concert

Saturday, July 8, 5-8 p.m. at Eddie Collins Memorial Park, Millerton

Enjoy a summer evening of free, family-friendly fun in the scenic northeast corner of Dutchess with the classic rock and country rock sounds of the Steve Dunn Band. Local food trucks and vendors will provide all sorts of tasty bites, as well as wine, beer and soft drinks. Click here for updates.

Jazz in the Valley
Jazz in the Valley, Victor C. Waryas Park, Poughkeepsie

Jazz in the Valley 

Sunday, Aug. 20 12 p.m. at Victor C. Waryas Park, Poughkeepsie 

This annual festival welcomes world-class musicians to the banks of the Hudson River for a celebration of jazz the whole family will enjoy! Grab a bite to eat at one of the local food trucks scheduled to be on-site. Bring your own chair or blanket and relax on the lawn or sit under the tent. Stay tuned for this year’s lineup; for updates and information, click here. Waryas Park is within walking distance of the Poughkeepsie train station, so getting there is a snap by Metro-North or Amtrak.

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.   

Dutchess County Fair Rhinebeck
Dutchess County Fair, Rhinebeck

Brantley Gilbert at the Dutchess County Fair 

Wednesday, Aug. 23, 7:30 p.m. at the Dutchess County Fairgrounds, Rhinebeck 

Along with an endless supply of tasty food and beverages and an action-packed lineup of carnival rides, livestock shows and competitive, historical and educational exhibits, this year’s Fair features a concert on the Grandstand Stage by country music star Brantley Gilbert, whose “Get Rollin’” North American tour kicks off this spring. Click here to purchase tickets. There will also be daily musical acts and events that are free to attend with paid Fair admission. These include Cooper Alan with special guest Chase McDaniel (Aug. 22), the Steve Augeri Band (Aug. 24), Chris Cagle (Aug. 25), Refugee: A Tom Petty Tribute Band (Aug. 26) and the Dutchess Fair Highland Games (Aug. 27). For more than 170 years, the Dutchess County Fair has been a summer highlight in the Hudson Valley. It is the second-largest county fair in New York State and one of the biggest in the country. While you’re at the Fair, be sure to treat yourself to a Dutchess County Dairy Committee milkshake at the 4H building. These famously delicious shakes come in vanilla, chocolate and strawberry and are made with local Hudson Valley Fresh milk.  

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

Poughkeepsie PorchFest Music Festival 

Sunday, Aug. 27 in Poughkeepsie 

Take a leisurely stroll through Poughkeepsie’s Southside Historic District and be a part of this free, family-friendly live music event! Walk along Academy, Garfield, Barclay and Montgomery streets to hear local musicians perform right on the front porches of the neighborhood’s beautiful homes! For updates, click here.

Hudson Valley Rodeo Keene Stud Amenia
Hudson Valley Rodeo, Keene Stud, Amenia

Walker Hayes at the Hudson Valley Rodeo 

Saturday, Sept. 16, 7 p.m. at the Keane Stud, Amenia 

A concert featuring Grammy-nominated country music sensation Walker Hayes caps a day of family-friendly fun at the third annual Hudson Valley Rodeo. It’s a great way to wrap up an exciting day of barrel racing, roping, bronc riding and bull riding. Of course, the mutton bustin’ contest is always a fan favorite! Hayes’ 2021 hit song “Fancy Like” spent more than six months in the No. 1 spot on the Billboard Hot Country Songs Chart. Click here for ticket options. 

Hudson Valley Gospel Festival
Hudson Valley Gospel Festival

Hudson Valley Gospel Festival 

Saturday, Sept. 30, time and location to be announced 

Let your spirit soar as Arts Mid-Hudson presents an afternoon of gospel singers, choirs and praise dancers! Stay tuned for more information. 

Beacon Bonfire photo by Daniel Rowan
Beacon Bonfire (photo by Daniel Rowan)

Beacon Bonfire Music and Arts Festival 

Saturday and Sunday, Nov. 4-5 in Downtown Beacon 

With more than 100 artists performing at more than a dozen venues in Beacon, the inaugural Beacon Bonfire event was a tremendous success last November, and this year’s event is sure to be another blockbuster. Snuggle up by one of the crackling bonfires burning all along Main Street. Take advantage of discounts on food and beverages, as well as services and retail items. More details to come; click here for updates. 

The Beacon Free Loop provides free bus service from the Beacon Metro-North train station to Main Street and other points in the city from 6 a.m. to 9 p.m. Monday through Saturday, so getting there is easy-peasy! 

Many establishments throughout Dutchess host outdoor concert series during the warmer months, often featuring popular local acts. Check out these lineups, and you’re sure to come back again and again: 

The Big Band Sound
The Big Band Sound

Northern Dutchess County 

Harmonies on the Hudson: Enjoy live music on the banks of the Hudson River as Clermont State Historic Site hosts the Harmonies on the Hudson Concert Series. Be sure to bring a lawn chair or blanket, perhaps a picnic dinner, if you like. Performances will be held near the Arryl House ruins. Tickets are free, but registration is required. Upcoming acts include Girl Blue (May 25), Setting Sun (June 15) the Wallpapers (July 13) and the Donna Tritico Band (Aug. 17). For more information and to register, click here. Tours of the Livingston family's mansion are held Thursdays through Sundays, as well as Monday holidays. The exterior grounds and gardens, including five miles of marked nature trails and three miles of marked bridle trails, are open daily from 8:30 a.m. until dusk. 

Music in the Parks in Hyde Park: Vanderbilt Mansion and Mills Mansion provide scenic backgrounds for an action-packed summer of music. Concerts at Vanderbilt include: the Hyde Park Central School District Bands (June 7), the Jim Osborn Band (June 21), Soul Purpose (July 12), the West Point Military Band (July 19, rain date July 20), Chain Gang (Aug. 2) and Roadhouse (Aug. 16). Concerts at Mills include: Thunder Ridge (June 14), The Big Band Sound (June 28), 4 Guys in Disguise (July 26) and the Southern Dutchess Concert Band (Aug. 9). In the event of rain, the concerts will move to the New York State Office of Parks, Recreation and Historic Preservation’s Taconic Region facility in Staatsburg (except the West Point Military Band concert, which will be held the following day at Vanderbilt). For details and updates, click here.

Rhinebeck Chamber of Commerce Music on Market: Enjoy Rhinebeck's downtown shopping and eateries while listening to light music on select Fridays and Saturdays from June 2 through Sept. 1. The schedule includes The Duo (June 2), the Hudson Valley Chamber Music Trio (June 10), Erin Hobson (June 16), the Stissing Mountain Boys (June 24), Blue Gardenia (June 30 and Aug. 11), the Bossa Blue Trio (July 8), Tim Hoolihan (July 14), Jasparro (July 28), the Al Wolcott Trio (Aug. 19) and guitarist Benji Kaplan (Sept. 1). Acts for the July 22 and Aug. 5 events will soon be announced. For updates, click here.

Millbrook Vineyards and Winery
Millbrook Vineyards and Winery, Millbrook

Eastern Dutchess County 

Millbrook Arts Group Free Live Music Saturdays: The Millbrook Arts Group hosts a wide variety of free shows on select Saturday mornings in May, June and July, featuring everything from rhythm and blues to jug band music. Head to the George T. Whalen Insurance Agency on Franklin Avenue for performances on the lawn by the Burr Johnson Band (May 20), Jasperoo (June 3), Nitetrain (June 10) and Grandpa Joe’s Washboard Band (June 17). Stop by the Millbrook Farmers and Makers Market on Franklin Avenue to see the Jordan Stoner Band (May 27) and Damian Ecco (July 1). Click here for updates. 

Jazz in the Vinyard at Millbrook Vineyards and Winery: Relax with a glass of wine and enjoy the swinging sounds of local jazz bands out in the vineyard every Saturday at 5:30 p.m. from June 24-Sept. 2. Don’t forget your lawn chairs and picnic blankets, and be sure to sample some tasty treats from a variety of Hudson Valley food trucks. Performers include the Swing Vipers (June 24), the 3 B’s Plus 2 (July 1), Larry Ham with Woody Witt (July 8), the Yvonnick Prene Trio (July 15), the HotClub of Black Rock (July 22), the Howard Britz Trio (July 29), Mary Ann Palermo and the First Take Band (Aug. 5), the Blue in Green Jazz Quartet (Aug. 12), an act to be determined (Aug. 19), Out of the Box Jazz (Aug. 26) and the Daniel Bennett Group (Sept. 2). For additional details and to purchase tickets, click here.

Friday Night Food Trucks at Millbrook Vineyards and Winery: Local musicians, local food trucks and Millbrook Wine – it's the perfect combination! Bring your own chairs, blankets and lawn games. Above all, admire the beauty of summer sunsets in one of the Hudson Valley’s prettiest wineries. This series runs on Fridays from May 26 through Sept. 15, and no reservations are needed. For a complete schedule of food trucks and musical acts, click here.

Abby Payne photo by Amanda Kaye
Abby Payne (photo by Amanda Kaye)

Central Dutchess County 

Plan Bee Farm Brewery Sunset Music Series: Plan Bee Farm Brewery presents concerts featuring talented local musicians on their Farmstand Stage on select dates throughout the summer. Show your support of local musicians and watch the sunset behind the stage on the beautiful 25-acre farm with a glass of cold craft beer in your hand! The mural on the stage was designed by artist Natalie Renganeshi and will change visually with the setting sun. This summer’s lineup includes Robbie Gil (July 14), Nicky Barbato (July 21), Paris Monster (Aug. 18), Tim Haufe (Sept. 8) and Abby Payne (Sept. 15), as well as a double feature on Aug. 19. The brewery’s own co-founder Evan Watson will also take the stage for several performances throughout the season. Boxed dinners from Rossi’s are available, but they must be preordered when you buy your tickets. Lawn chairs, picnic blankets and benches are available, but feel free to bring your own. Click here to purchase tickets. These concerts will go on rain or shine. In the event of inclement weather, the music will move inside or under Plan Bee's new pavilion. 

Poughkeepsie Summer Nights Concert Series: Head over to Greenvale Park for a free concert each Tuesday night from June 27 through Aug. 15! Bring a lawn chair or a blanket and catch great local bands, including Crew (June 27), Lucky House (July 11), Noise in the Basement (July 18), Hillbilly Parade (July 25), Euphoria Classic Rock (Aug. 1), The Chain Gang (Aug. 8) and Thunder Ridge (Aug. 15). There will be no concert on July 4. Click here for information and updates.   

LaGrange Summer Concert Series: The bandshell at Freedom Park will host free shows featuring great local bands on select Sundays from June through September. Be sure to bring your appetite, as each concert will include a local food truck. Musical acts include the Carrie Zazz Band (June 25), Nashville Drive (July 9), The Chain Gang (July 23), the Southern Dutchess Concert Band (Aug. 13), Jungle Love (Aug. 27), Grooved Pavement (Sept. 10) and the Hurley Mountain Highway Band (Sept. 24). For details, click here.

Cannon Street Block Party: Every second Sunday from June through August, the King’s Court Brewing Company throws a block party on Cannon Street in Poughkeepsie with live music, food vendors, craft beer, fine wine and plenty of fun! Come see the best of what downtown Poughkeepsie has to offer. 

Bannerman Castle Pollepel Island Beacon
Bannerman Castle, Pollepel Island, Beacon

Southern Dutchess County 

Third Sundays at Bannerman Island: Take a 30-minute boat ride over to Bannerman Island aboard the Estuary Steward ferry and take a self-guided tour of the island. Explore the famous Bannerman Castle ruins and gardens, and then stay to enjoy a live music performance! Upcoming acts include the Toland Bros. (May 21), Thomas McCoy (June 18), Tony DePaolo (July 16), Darryl Brown & Little Bones (Aug. 20), Jeffrey Kirn (Sept. 17) and Thistle (Oct. 15). To book your tour, click here.


East Fishkill Music in the Park Series: Catch free live music every Friday night and select Saturdays at Hopewell Recreation Park. Bring your own lawn chairs, blankets and snacks. From covers of classics to jazz and rock, check out the lineup of performers coming this summer, which includes the Hudson Valley Council Band (June 16), The Harvest Band (June 23), Adam & The Newhearts (July 1, Fireworks Night), Everything Else (July 7), Special Sauce (July 8), Cherished Memories (July 14), Bosco and the Storm (July 21), Chain Gang (July 28), the Hurley Mountain Highway Band (Aug. 4), Roadhouse 60s (Aug. 18), Steel Owl (Aug. 25), and Johnny Dell & Nite Life – Reunion Band (Sept. 2). For more details, click here.

Fishkill Summer Concerts in the Park: Bring a lawn chair or a blanket and come down to Maurer-Geering Park most Wednesdays in July and August for a free concert. Bring your own food and drinks. It’s the perfect mid-week outing. Acts this summer include Nite Life (July 5), The Saints (July 12), the Southern Dutchess Concert Band (July 19), the Carrie Zazz Band (July 26), Everything Else (Aug. 9), the Christine Spero Duo (Aug. 16), the Tracy DeLucia Band (Aug. 23) and Raquel and the Wildflowers (Aug. 30). For updates, click here.

DC Sports Bands in the Sand: You don’t need to travel to the seaside for sandy feet and live music! Grab your sandals and your beach chairs and head to DC Sports in Wappingers Falls on select Saturdays for its free live concert series, Bands in the Sand. Arrive early for a round of mini golf! Food and drinks are available. Upcoming shows include the Jukebox Junkies (June 10), Seeing Red (June 17), G! Force (July 22), Rumor Hazz It (July 29), Moo Crue (Aug. 12) and Jungle Love (Aug. 26). Click here for updates. 

Wappinger Summer Concert Series: Head to the bandshell at Brexel-Schlathaus Park for a free concert under the stars on select Thursday nights in July and August. Bring a lawn chair or a blanket, and feel free to pack a picnic. Check out this year's lineup: Bosco and the Storm (July 13), Johnny Dell and Nite Life (July 20), Midnight Slim and Laurie Ann (July 27), the Southern Dutchess Concert Band (Aug. 3), Cloud NYne (Aug. 10) and Jungle Love (Aug. 17). Click here for updates.

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