It’s time for live outdoor music, friends. What could be better?  

By Sean McAlindin

My favorite midsummer pastime has to be listening to live music outdoors. There’s something about the sun and the wind, the music mingling with the sounds of nature, the beautiful people blissing out around me—it all blends in a dreamy vision that might as well be heaven.

Far too many live concerts exist in our short, sweet summer to cover in one story. From Williamstown to LaGrange and Catskill to Great Barrington, free performances happen each week in many hamlets, towns and cities throughout our storied region. Historical sites and scenic landmarks get in on the fun at places like Berkshire Botanical Garden, Millbrook Vineyards, Walkway over the Hudson, Catamount Mountain Resort and Vanderbilt Mansion.

As the north-of-New-York-City population swells in the summertime, so too does the performance lineup. From front porches and village squares to world-class arenas, there’s music happening wherever and whenever you go. So get out there and enjoy the summer world and the sounds that live in it. 

Here are our picks for the best outdoor concerts in the mountains this summer. 

Let’s start with the open-air amphitheaters that attract the year’s biggest tours.

Bethel Woods Performing Arts Center has put together an incredible schedule accentuated by Scottish songwriter Hozier on July 27, jam icons Phish from August 9 to 11, feminist rockers Melissa Etheridge and Indigo Girls on August 21, EDM journeyman Pretty Lights on August 23 and 24, and the downhome Tedeschi Trucks Band on August 25. 

Saratoga Performing Arts Center (SPAC) brings bonafide country star Dierks Bentley on July 18, Angélique Kidjo with the Philadelphia Orchestra on August 2, pop genius John Legend on August 7, ’80s idols New Kids On The Block, Paula Abdul and DJ Jazzy Jeff on August 11, Berkshires-based songwriter James Taylor on September 2, Connecticut groovers Goose on September 6 and 7 and the one and only Cuban-American hip hop sensation Pitbull on September 8.

Fabled Tanglewood in Lenox offers weekly classical music and open rehearsals with Boston Symphony Orchestra along with one-off concerts featuring the Pretenders on July 16, Beck with the Boston Pops on July 23, Judy Collins, Indigo Girls and Rufus Wainwright on August 30 as well as DISPATCH on August 31.

Now, it’s time to move on to one-of-a-kind venues that attract both regional talent and nationally touring musicians. Arrowhead Farms in Accord is a laid-back location featuring everyone’s aunt and uncle Larry Campbell and Teresa Williams’ “July Jam” on July 20 with Hot Tuna, Connor Kennedy and The Secret Sisters. Indie faves Waxahatchee, Tim Heidecker and Snail Mail play on August 31 and the Woodsist Festival hosts critics’ darlings Yo La Tengo, Real Estate, Jessica Pratt and Bonnie “Prince” Billy on September 21 and 22.

Looking for some multicultural music inside an environmental sculpture garden? Soak up some song amid the monoliths and intricate stonework of Opus 40 in Saugerties with Pakistani-American singer Arooj Aftab on July 25, Kingston songwriter Larry Locust on July 28, Zimbabwean Afro-pop stars Mokoomba on August 2 and Orlando experimental metal band Beings on August 8. 

Or should the mood strike, sip vino as you vibe at City Winery Hudson Valley with Vino Palooza on July 28, Soul & Funk Fest on August 11, electro-folk duo Tall Heights on August 22, and Iowa roots musician William Elliott Whitmore on September 29. 

Across the river, the al fresco Spiegeltent returns to SummerScape at Bard College in Annandale-on-Hudson with mandolinist Sierra Hull on August 1 and art rocker Nona Hendryx on August 17.

In Woodstock, Colony has a cozy beer garden with up-close talent such as songwriting progeny Loudon Wainwright III on July 20. Amidst a jam-packed indoor lineup, Bearsville Theater will host the Festival of Awakening on August 10, Art Festival on August 17, Country Festival on September 1 and Fall Festival on September 21. The nearby Maverick Concerts hosts Palestinian oud player Simon Shaheen Trio on August 3, pianist Jenny Lin on August 30 and Puerto Rican alto saxophonist Miguel Zenón Quartet on September 7.

As for Hudson, Park Theater opens its doors to Warren Street for artists such as trans-punk glam rocker Venus de Mars on August 3, outlaw blues guitarist Emanuel Casablanca on August 16 and the darkly humorous Brian Dunne on August 17. The renovated back patio of Isaan Thai Star hosts Colorado crooners Stillhouse Junkies on July 26, Sheffield soul singer Wanda Houston on August 23 and local pianist  Armen Donelian on select nights throughout the summer.  

Up river in Schenectady, Frog Alley Brewing Company has a bangin’ backyard scene with G. Love & Special Sauce on July 28, Andrew Bird on August 13 and Dark Star Orchestra on August 22. Other not-to-miss music events in the capital district include the Albany Riverfront Jazz Festival on September 14 and PearlPalooza on September 21. 

And don’t forget—Dutchess County Fair in Rhinebeck has invited Rick Springfield to perform on August 21. “Jessie’s Girl,” anyone?

Did somebody say festivals? Well, we’ve got options to spare. 

Grey Fox Bluegrass Festival is in Oak Hill from July 17 to 21 with bluegrass phenoms Del McCoury, Molly Tuttle and Darol Anger. Podunk Bluegrass Festival in Goshen, CT presents John McEuen & The Circle Band and Della Mae from August 8 to 11.

Summer Hoot at Ashokan Center in Olivebridge from August 23 to 25 provides three eclectic days of music, nature and community with The Mammals, Tuba Skinny, Steve Poltz and so many more. Meadowlark in Stone Ridge on September 14 and 15 is an indie pop paradise with Fruit Bats, Blonde Redhead, Deer Tick, Slaughter Beach, Dog and Laura Stevenson. MASSMoCA puts on FreshGrass from September 20 to 22 with Shakey Graves, The Devil Makes Three and Drive-By Truckers, to name a few. 

Plan Bee Farm Brewery in Poughkeepsie is planning the DIY Big Lawn Music Festival on August 3. Then take a leisurely stroll through the Southside Historic District on August 25 for Poughkeepsie PorchFest to hear local musicians perform right on the front steps of the neighborhood’s beautiful homes. The third annual Hudson Valley Wine & Music Festival at People’s Park in Newburgh showcases R&B artists Chubb Rock and Ruff Endz on August 31. 

Do you happen to love classical music?

The Orpheum Performing Arts Center in Tannersville hosts “A Midsummer Night’s Dream” on August 3 and 4, Lysander Piano Trio on August 10 and Windham Festival Orchestra on August 17. Norfolk Chamber Music Festival in Norfolk, CT plays to the theme of Charles Ives and the American tradition through August 17. 

Music Mountain Summer Festival in Falls Village has outdoor performances on Saturdays and Sundays through September 15. Berkshire Opera Festival performs the great Gounod’s “Faust” on August 24, 27 and 30 in Pittsfield, MA and the world-renowned Jacob’s Pillow Dance Festival goes through August 25 in Becket. 

Maybe jazz is your bag, baby? Litchfield Jazz Festival runs July 26 to 28 with saxophonist Alexa Tarantino and pianists Bill Charlap and Amina Figarova. Jazz in the Valley leads with poet Nikki Giovanni and vocalist Nnenna Freelon at Victor C. Waryas Park in Poughkeepsie on August 18. Bousquet Jazz Festival in Pittsfield brings renowned Brubeck Brothers Quartet and vocalist Samirah Evans on August 17.

And don’t even get me started on the incredible lineup of indoor concerts at venues including The Falcon in Marlboro, Palace Theater in Albany, Levon Helm Studios in Woodstock and Ulster Performing Arts Center in Kingston. I’m talking Nas, Cat Power, God Street Wine, Yellowman… the list goes on. We’ll see you there.

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