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Catbird FESTIVAL photo with the "Upstate Weekend Plans" text written across the photo for the Hudson Valley, NY

What To Do In The Hudson Valley This Weekend Aug 18 – Aug 20

By inside + out | August 17, 2023

Music Festivals, Comedy 🎸 Hiking + more! Upstate NY has events for all ages this weekend 🌞 Take your pick below…

☮️ Woodstock, Thurs Aug 17th – Sun Aug 20th. Woodstock Summer School Series of Workshops.
Mothership Gallery + Studio presents an introduction to Woodstock. We celebrate its legacy of over a century of being an artists’ enclave and a half-century of birthing the New Age from the embers of sex, drugs and rock’n’roll with a series of workshops by local legends. Info HERE.

⛰️ Highmount, Fri Aug 18th, 6:00 PM. Music on the Belle – The Trapps.
Enjoy live music, indulge in delicious food + drinks, take a scenic gondola ride above the Catskill Mountains, or challenge friends to lawn games at Belleayre Mountain. Info HERE.

🎙️ Windham, Fri Aug 18th, 6:00 PM – 9:00 PM. Country Club Comedy Night.
An evening of stand-up comedy with NYC-based comedy superstar Amanda Gail at Christman’s Windham House. Info HERE.

🤸‍♀️ Beacon, Fri Aug 18th, 6:30 PM – 7:30 PM. Weekly Improv Jam.
Dip your toes in the improv waters + sharpen some skills at Serious Comedy Theatre. Info HERE.

🖼️ Woodstock, Fri Aug 18th, 6:30 PM – 9:00 PM. Monthly SoulCollage® Card Making Studio with Nixa.
Come awaken an inner part of yourself and mind with SoulCollage at Everyday Magic Intentional Goods + Healing. Info HERE.

🎩 Hudson, Fri Aug 18th, 7:00 PM. Dmitry Wild Show at Park Theater.
Vintage rock, garage, psych, carnival in a bowler hat. Info HERE.

🌌 Poughkeepsie, Fri Aug 18th, 8:00 PM – 9:30 PM. Walkway at Night.
Enjoy breathtaking Hudson Valley views after dark from 212 feet above the Hudson River at Walkway Over the Hudson. Info HERE.

🌻 Leeds, Fri- Aug 18th – Sun Aug 20th, 11:00 PM – 7:00 PM. Sunflower & Sangria Festival.
Meadowbrook Farm Catskill will have food, sangria, beer, live music, vendors, hayrides, cornhole contests and Sunflower fields forever! Info HERE.

🍺 Red Hook, Sat Aug 19th, 11:30 AM – 9:00 PM. Deep In The Valley.
From The Ground Brewery hosts a second year of live psych, jazz, jam, experimental, country & folk music with food trucks and more. Info HERE.

🫶 Woodstock, Sat Aug 19th. 2:00 PM – 9:30 PM. Woodstock Volunteer Festival.
A day of celebration for Woodstock’s volunteers with lunch, a concert, fun activities + fireworks. Info HERE.

🍃 Mount Tremper, Sat Aug 19th. Hike for the Catskills.
Explore the natural beauty of the Catskills while helping to protect critical Catskills Habitats, held by Catskill Center. Info HERE.

🏟️ Bethel, Sat Aug 19th – Sun Aug 20th. Catbird Music Festival.
A gathering of the most exciting and enticing musical acts around at Bethel Woods Center for the Arts. Info HERE.

🎸Woodstock, Sat Aug 19th, 2:00 PM – 4:00 PM. Levon Helm: Rock, Roll & Ramble—The Inside Story of the Man, the Music and the Midnight Ramble.
Historical Woodstock Society will be talking with John W Barry about his book on local legend Levon Helm and his manager Barbara O’Brien. Info HERE.

🛖 Rosendale, Sun Aug 20th, 10:30 AM – 7:30 PM. Rail Trail Cafe Assortment of Events.
Luke Sarrontonio: Mushroom Love: Talk and Walk learn about the interwoven lives of organisms that make up the diverse Ecology of our region. Next, Sound Healing and performance art with Sonic Elixirs. Ending with live music by Levanta (cash ONLY). Info HERE.

🎈 Kingston, Sun Aug 20th, 1:00 PM. Kingston Artists Soapbox Derby.
A parade of non-motorized kinetic sculptures through lower Broadway in Kingston, NY. Info HERE.

🌽 Hudson Valley Area, Check out the Hudson Valley Farmer’s Markets near YOU!
From year-round to seasonal markets, here’s your insider’s go-to Hudson Valley Farmer’s Markets. Info HERE.


👉 Know of more cool events happening in the Hudson Valley/Catskills area?
Leave them in the comments below.

Have a wonderful weekend from Inside+Out Upstate NY!


  • Kerrville New Folk winner John John Brown is bringing giant comics and iconic photographs to the Park Theater stage Saturday August 19th. Titled Songs, Stories, & Art- Lessons from Strangers, this original project weaves together storytelling songs and the visual arts in a live performance. Throughout the concert, Brown unfolds an imaginative and colorful world revealing the idea that all people, strangers alike, have a story we can learn from. With his guitar in hand, John John may have found a new way to sing a song. Above all, he stays rooted in the soil of a good story.

    August 18, 2023
    • inside + out

      Thank you for sharing – sounds like a fab event!

      August 19, 2023

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