Enjoy Outdoor Concerts in Dutchess County

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): 

Bernie Williams Jazz at the Vineyard

Saturday, Aug. 3, 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.”

Big Lawn Music Festival

Saturday, Aug. 3, 12 p.m.–10 p.m. at Plan Bee Farm Brewery, Poughkeepsie

This annual outdoor music festival returns to Plan Bee and features a lineup of more than a dozen acts from the Hudson Valley, New York City and beyond and ranging from rock to indie to rap. This festival is a way for up-and-coming artists to reach their audiences and get to know other bands. The 2024 roster once again features women, queer, and gender non-conforming performers. This year's festival will include the new Writers' Round songwriters workshop from 2–4 p.m. in the Plan Bee Farm Brewery Pavilion; writers can perform their works in progress and receive feedback from fellow artists. Yum Yum Hot Spot food truck will be on hand serving delicious food. For more details and to purchase tickets, click here.

Jazz in the Valley 

Sunday, Aug. 18 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. This year's lineup includes Nikki Giovanni, Javon Jackson, Nnenna Freelon, Charles McPherson, the Brandee Younger Trio, and Mitch Frohman & The Bronx Horns. 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 

Aug. 20–25 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, visitors to this year’s Fair can also catch Grandstand Stage performances by three big-name acts who are sure to keep the Hudson Valley rocking into the night. Country music star Tracy Byrd takes the stage on Aug. 20, followed by pop music icon Rick Springfield on Aug. 21 and country performer Kameron Marlowe on Aug. 23. All three shows are set to begin at 7:30 p.m. Click here to purchase tickets. There will also be daily musical acts and events that are free to attend with paid Fair admission. 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. 25 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.

Beacon Bonfire Music and Arts Festival 

Dates TBA in Downtown Beacon 

Stay tuned for updates on this third-annual event. Last November, more than 25 venues hosted hundreds of performers during the two-day festival, which has grown exponentially each year. 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: 

Northern Dutchess County 

Harmonies on the Hudson: Enjoy a variety of live music performances on the banks of the Hudson River at Clermont State Historic Site. Be sure to bring a lawn chair or blanket, perhaps a picnic dinner, if you like. Performances are set for select Thursday evenings from May through September and will be held near the Arryl House ruins. Tickets are free, but registration is required. For more information and to register, click here. 

Music in the Parks: This popular summer concert series celebrates 50 years this year! Vanderbilt Mansion in Hyde Park and Mills Mansion in Staatsburg provide scenic backgrounds for an action-packed summer of live music. Concerts will be held Wednesday evenings from June through mid-August (except July 3). For details and updates, click here.

Eastern Dutchess County 

Millbrook Arts Group Summer Sunsets Concerts: The Millbrook Arts Group hosts a wide variety of free shows on select Saturday evenings from late June through late August at the Millbrook bandshell. Click here for updates. 

Jazz in the Vinyard: Relax with a glass of wine and enjoy the swinging sounds of local jazz bands out in the vineyard at Millbrook Vineyards and Winery every Saturday evening from late June through late August. 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. 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 from late May through early September, and no reservations are needed. For a complete schedule of food trucks and musical acts, click here.

Central Dutchess County 

Plan Bee Farm Brewery Concerts: Head to Plan Bee Farm Brewery in Poughkeepsie for a jam-packed lineup of concerts featuring talented local musicians on their Farmstand Stage on select dates throughout the spring, summer and early autumn. Plan Bee's SunSet Music Series returns for a fifth season and will run from May through early October. But wait, there's more! On the night of the full moon each month, Plan Bee Farm Brewery owner and head brewer Evan Watson takes the stage for a night of original tunes and good times. Show your support of local musicians this summer and watch the sun set 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. Lawn chairs, picnic blankets and benches are available, but feel free to bring your own. Click here to see the full schedule and to purchase tickets.

Poughkeepsie Summer Nights Concert Series: Head over to Greenvale Park for a free concert Tuesday nights from late June through mid-August. Bring a lawn chair or a blanket and catch great local bands. Local food trucks will be on site serving up delicious treats. 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 Sunday evenings from late June through late September. Be sure to bring your appetite, as each concert will include a local food truck. For details, click here.

Summer Sundays on Cannon Street: Every second Sunday from June through September, the businesses on Cannon Street in Poughkeepsie throw a block party with live music, food vendors, craft beer, fine wine and plenty of fun! Come see the best of what downtown Poughkeepsie has to offer. Click here for details.

Southern Dutchess County 

Third Sundays at Bannerman Castle: Take a scenic 30-minute boat ride from Beacon over to Pollepel 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! To book your tour, 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. 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 in June, July and August for its free live concert series, Bands in the Sand. Arrive early for a round of mini golf! Food and drinks are available. Click here for updates.