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Outdoor Summer Concerts in Dutchess County

Date Published: June 1, 2022

Outdoor music performances come in all shapes and sizes: fist-pumping rock and roll, toe-tapping jazz, red-hot flamenco – and everything in between. With dozens of venues in Dutchess County hosting all types of outdoor concerts this spring and summer, there will certainly be something for everyone. Here are some of the highlights:

Natalie Merchant
Natalie Merchant (photo by Marion Ettlinger)

Natalie Merchant at Kaatsbaan 

Friday, June 3, 6 p.m. at Kaatsbaan Cultural Park, Tivoli 

The Summer Soiree fundraiser will open Kaatsbaan’s Summer Festival with an intimate concert and dinner featuring legendary singer-songwriter Natalie Merchant and celebrity caterer Mary Giuliani. A native of Western New York, Merchant was the lead vocalist of the 10,000 Maniacs for more than a decade before embarking on a successful solo career in the early 1990s. Seating is limited to 100 guests at Kaatsbaan, a scenic 153-acre artist’s sanctuary on the banks of the Hudson River. To purchase tickets, click here.  

The Big Band Sound
The Big Band Sound

The Music of Ella Fitzgerald and Frank Sinatra at Freedom Park 

Friday, June 3, 6 p.m. at the Freedom Park Bandshell, LaGrangeville 

The Big Band Sound 25-piece jazz orchestra performs the music of Ella Fitzgerald and Frank Sinatra in its "Ella and Frank, Big Band Style" show. The proceeds benefit the local Sparrow's Nest of the Hudson Valley, a charity that provides meals to the families of caregivers and children diagnosed with cancer.

Taylor Mac
Taylor Mac

Taylor Mac at Kaatsbaan

Saturday, June 18, 6 p.m. at Kaatsbaan Cultural Park, Tivoli

Taylor Mac and friends pay homage to queer icons of the past and present in this work-in-progress concert on Kaatsbaan's breathtaking open-air Mountain Stage. Be the first to see a selection of all-new original songs co-written with composer and music director Matt Ray! Mac is reunited with longtime collaborators co-director Niegel Smith, choreographer Faye Driscoll, costume designer Machine Dazzle and creative producers Pomegranate Arts. Mature audiences only. Bring your own lawn chair or picnic blanket. To buy tickets, click here.

Bernie Williams
Bernie Williams at Millbrook Vineyards and Winery

Bernie Williams at Millbrook Vineyards and Winery 

Saturday, June 25, 7 p.m. at Millbrook Vineyards and Winery, Millbrook 

Former New York Yankees all-star centerfielder Bernie Williams – who is also an extraordinary guitarist and a wine aficionado - presents a night of jazz at Millbrook Vineyards and Winery. Come and join the four-time World Series champion, whose unique style blends jazz, rock and a taste of the tropical sounds of his Puerto Rican heritage. The winery has crafted "Bernie's Blend," a combination of Cabernet and Merlot with a little Zinfandel for spiciness, which will be available to taste and purchase at the concert. Food trucks will be onsite, and wine will be available. To purchase tickets, click here. 

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: 

Denise Parent
Denise Parent

Northern Dutchess County 

Harmonies on the Hudson: Enjoy live music on the banks of the breathtaking Hudson River as Clermont State Historic Site is bringing back the Harmonies on the Hudson Concert Series. Groove to the folk, rock and blues vibes of Denise Parent with Rock City Junction (June 16). Catch the husband-and-wife duo of Andy and Shannon Schober as Shandy brings its folksy sound to Clermont (July 14). Tickets are free, but registration is required. For more information, click here.     

Live Music at Dutch's Spirits in Pine Plains: Sip summer cocktails and enjoy free live music every Saturday evening on the great lawn of Dutch’s Spirits. This unique Hudson Valley distillery was built on the site of the largest bootlegging operation ever found in Dutchess County during Prohibition. Acts include Nellybombs (June 4), the Emily Beck Band (June 11) and the Bob Stump Band (June 18), to name a few. For more details, click here.  

Check out our guide to Dutchess County's craft breweries. 

Music in the Parks Concert Series in Hyde Park: Vanderbilt Mansion and Mills Mansion provide scenic backgrounds for an action-packed summer of music. Acts include Evil Genius (June 8), the West Point Military Band (July 20) and Bill’s Toupee (Aug. 3). For a full schedule of events, click here. 

Rhinebeck Area Chamber Music on Market: Enjoy Rhinebeck's downtown shopping and eateries while listening to light music on select Fridays and Saturdays throughout the summer and early autumn. For more information, click here. 

Music on the Elmendorph Green: The historic Elmendorph Inn provides the backdrop for a fun summer concert series in Red Hook. Built in the mid-1700s, the Elmendorph Inn was once a popular stopover on the four-day stagecoach ride from New York City to Albany! These days, folks come from miles around to catch great local bands performing on the lawn. The concerts are held on select Saturdays in June and July and feature such bands as New Breaks (June 4) and R.J. Storm and the Old Bluegrass Band (July 16). For a complete schedule of concerts, click here. 

Summer Concerts at Greig Farm: Pick your own produce all summer long at Greig Farm in Red Hook and catch some great local bands while you're there! Strawberries and peas will be coming into season when the Dan Palladino Quartet plays at Greig Farm on June 4. Blueberries and blackberries will be ripe for picking when Brad Armstrong takes the stage on July 16. It’ll be pumpkin season when Stella Prince rounds out the summer series on Sept. 17. For a complete schedule of concerts, and to see all the fruits and veggies available to pick at Greig Farm, click here.  

Rhinebeck PorchFest Music Festival: Rhinebeck PorchFest is set for Sept. 24, and this year’s event will kick off the “Fields for Our Youth” campaign to build a multipurpose field at Thompson-Mazzarella Park. Take a walk down Livingston and Chestnut streets and there will be local musicians playing on front porches everywhere you turn. It’s a family-friendly music event you don’t want to miss! For updates, click here. 

Back to the Garden 1969
Back to the Garden 1969

Eastern Dutchess County 

Pawling Music by the Lake, Beach Edition: This free, family-friendly concert series welcomes visitors of all ages to Lakeside Park, a tranquil destination in Eastern Dutchess! Bring chairs, blankets and a picnic while enjoying the sounds of local bands like Raquel and the Wildflowers (June 11), Back to the Garden 1969 (July 16), Amrod Band (Aug. 13) and All in Band (Sept. 10). For more details, click here.  

Summer Sunsets Concert Series in Millbrook: Hurry over to the bandshell on Franklin Avenue on select Saturday evenings in June, July and August for a wide variety of free shows! The Hudson Valley Flamenco Festival gets things cooking on June 18. Additional acts include Soul Purpose (July 16) and the Saints of Swing (Aug. 13). For details, click here. 

Jazz Concert Series at Millbrook Vineyards and Winery: Relax with a glass of wine and enjoy the swinging sounds of local jazz bands out in the vineyard! Sample tasty treats from Hudson Valley food trucks. Bands include the Lucky 5 (July 2), Mary Ann Palermo and the First Take Band (Aug. 6) and the Daniel Bennett Group (Sept. 3), to name a few. 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 to kick off your weekend in Dutchess. Above all, admire the beauty of summer sunsets in one of the Hudson Valley’s prettiest wineries. This series runs on Fridays through Sept. 2, and no reservations are needed. Musical acts include Carrie Zazz (June 10), Sierra Ashley (July 15) and Sound of Sunshine (Aug. 26), among others. For more information, click here. 

Abby Payne
Abby Payne (photo by Amanda Kaye)

Central Dutchess County 

Plan Bee Farm Brewery Summer Sunset Concert Series: Come out to Plan Bee Farm Brewery in Poughkeepsie to hear New York’s finest musicians on their FarmStand Stage! 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 summer lineup includes Paris Monster (June 18), Abby Payne (July 2) and Robbie Gil and the brewery’s own co-founder Evan Watson (several shows), among others. Reserve a table for you and your group or bring your own lawn chairs and picnic blankets. For details, click here. 

Check out the Dutchess Tourism Taste Finder craft beverage passport

Poughkeepsie Summer Nights Concert Series: Gather in Greenvale Park for a free concert each Tuesday night from June 28 through Aug. 16! Bring a lawn chair or a blanket and catch great local bands, including Thunder Ridge (June 28), Cloud Nyne (July 19) and Bosco and the Storm (Aug. 9). For additional details, click here. 

Summer Concert Series at Freedom Park in LaGrange: Head to the bandshell at Freedom Park for a free show featuring a great local band every  Sunday from July 10-31! Be sure to bring your appetite, as each concert will include a local food truck. Musical acts include Little Creek (July 10) and the Chain Gang Billy Joel Tribute (July 24). For details, click here. 

Poughkeepsie PorchFest Music Festival: Take a leisurely stroll through Poughkeepsie’s Southside Historic District on Aug. 28 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. 

Cannon Street Block Party: Every second Sunday from June through September, Cannon Street in Poughkeepsie hosts a street festival with live music, food vendors, craft beer, fine wine and plenty of fun! Come see the best of what downtown Poughkeepsie has to offer. Best of all, these block parties offer free admittance and free parking. 

Bannerman Castle
Bannerman Castle

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 part in 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 Wild Irish Roses (June 19) and the Flash Company Band (July 17). For more details, click here.   

East Fishkill Music in the Park Summer Concert Series: Catch free live music every Friday night, either on the field at Hopewell Recreation Park or at Red Wing 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. Acts include Jennifer Dreaper and the Ramblers (June 26), the Bob Martinson Band (July 10) and Noise in the Basement (Aug. 19). For more details, click here.   

Summer Concerts in the Park in Fishkill: Bring a lawn chair or a blanket and come down to Maurer-Geering Park every Wednesday in July and August for a free concert. Bring your own food and drinks (no alcohol). Acts this summer include Everything Else (July 6), October Sky (July 27) and Classic Rock Euphoria (Aug. 10), among others. For a list of events, 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 for its free live concert series, Bands in the Sand. Arrive early for a round of mini golf! Food and drinks are available, and of course, kids are welcome to join in on the fun. White Noize, a female-fronted rock cover band, kicks off the season June 4. For details, click here. 

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