2026 Editor’s Picks: What to Do in the Hudson Valley on Aug 28 – Aug 30

Late summer has a certain kind of magic up here… a little wild, a little weird + full of good music. This weekend brings story slams, guitar riffs echoing through a cave, a Trojan boat race down the Hudson, Grateful Dead tributes, sunflowers, county fairs + live music spilling into the hills. Here’s where to wander this weekend in the Hudson Valley NY. Hot List below…

ALL WEEKEND

🛶 Saugerties, Fri – Sun. Kayak + SUP Rentals with I Paddle New York.
Paddle the calm waters of Esopus Creek through the Esopus Bend Nature Preserve, with scenic views, wildlife + sandy spots to stop and swim. Beginner-friendly + great for families. Info HERE.

🎸 Woodstock, Fri – Sun. Woodstock Fingerstyle Guitar Festival at Woodstock Playhouse.
A weekend devoted to the art of fingerstyle guitar. Info HERE.

🪕 Olivebridge, Fri – Sun. Summer Hoot at Ashokan Center.
Three days of roots music, art, nature + community featuring 20+ acts, including The Mammals, Milk Carton Kids, Tuba Skinny, Gail Ann Dorsey + more. Info HERE.

🎪 Rhinebeck, Fri – Sun. Dutchess County Fair.
Six days of carnival rides, farm animals, food, exhibits + live entertainment at one of the Hudson Valley’s biggest county fairs. Info HERE.

🌻 Poughquag, Fri – Sun. Sunflower Festival at Barton Orchards.
Stroll through five acres of sunflowers, pick your own blooms, catch live music + enjoy food, drinks and farm fun. Runs Aug 28 to Sept 7. Info HERE.

🌹 Warwick, Sat + Sun. Grateful Dead Tribute Festival at Warwick Valley Winery + Distillery.
Two days of Grateful Dead music, tie-dye, live bands + laid-back summer vibes. Info HERE.

🎻 Hudson, Sat + Sun. Chamber Music Churchtown at Churchtown Dairy.
Mozart + Brahms inside the luminous Round Barn at a working dairy farm—a pretty spectacular setting for chamber music. Info HERE.

🍑 Hudson Valley, ALL weekend! Your Ultimate Guide to the Hudson Valley’s Vibrant Farmers Markets: Spring to Fall.
Your go-to guide to the Hudson Valley’s vibrant Farmers Markets, spring through fall—where fresh seasonal produce, local farms and community come together. Info HERE.

FRIDAY, AUG 28

🏛️ Kingston, 6:30pm. Alexis Coe: You Never Forget Your First at Senate House.
The bestselling presidential historian talks George Washington in a free evening program. Info HERE.

🎤 Woodstock, 7pm. These Hot August Nights: Story Slam at Maverick Concert Hall.
Say goodbye to summer with an evening of storytelling, as a lineup of talented storytellers takes on the ticking clock + gong. The phrase? “These Hot August Nights.” Info HERE.

🎩 Beacon, 7pm. The Prestige Dinner at Savage Wonder Art Center.
A four-course dinner with wine + two magicians working the room between courses, with close-up magic at the tables, live performances during dinner + a finale after dessert. Info HERE.

🎶 Woodstock, 8pm. The Devil Makes Three at Bearsville Theater.
Roots, blues + punk-inflected Americana from the genre-bending trio, with Lightnin’ Luke + DiTrani Brothers. Info HERE.

🥁 Kingston, 8pm. Kingston Calling: Battle of the Bands at Assembly.
Local bands go head-to-head in a showcase of Hudson Valley talent. Info HERE.

SATURDAY, AUG 29

🐦 Valatie, 8am. Fall Migration Bird Walk at Hand Hollow.
Join experienced birder Joanie Scheu for a guided walk in search of migrating songbirds + resident species. Perfect for beginners + seasoned birders alike. Info HERE.

🏃 Hudson, 8am. The Hudson Mile on Warren Street.
A fast, exhilarating mile through historic Hudson, welcoming seasoned runners + first-time racers alike. Info HERE.

🚣 Athens, 9am. The Trojan Paddling Race.
Paddlers launch from Selkirk or Kingston for a 20–22-mile, current-supported race down the Hudson, finishing in Athens. Open to most paddle + rowing craft, with cash prizes + a post-race celebration at Stewart House. Info HERE.

💃 Tivoli, 11am. Kaatsbaan Annual Festival.
An all-day arts festival with live music, dance, workshops + an evening concert by Valerie June, plus the return of the outdoor Mountain Stage. Info HERE.

🍣 Hyde Park, 6pm. Summer Sushi Omakase Dinner at Dassai Blue.
Michelin-starred Chef Tasuku Murakami presents an exclusive 16-course omakase experience featuring seasonal ingredients, exceptional craftsmanship + creativity. Enjoy an intimate sushi counter experience with each course prepared before your eyes, offering the chance to interact directly with the chef throughout the evening. Info HERE.

🎸 Woodstock, 7pm. Country Joe + The Fish at Colony.
Catch the last surviving members of the legendary psychedelic-rock group for a rare Hudson Valley appearance. Info HERE.

SUNDAY, AUG 30

🤝 Poughkeepsie + Highland, 1pm. Hands Across the Hudson at Walkway Over the Hudson.
Bring the community together for an afternoon of music, singing, speakers + joining hands across the Walkway in a celebration of connection, community + shared values. Open to all; registration required and attendance capped at 1,000. No signs permitted. Info HERE.

🎸 Rosendale, 3pm. Dylan Doyle at Widow Jane Mine.
Gritty guitar, poetic songwriting + a genre-bending blend of Funk, R&B + Jazz from the Hudson Valley musician known for his powerful stage presence and deeply emotional, dance-worthy performances. More about Dylan Doyle HERE. Info HERE.

Photo by iPaddle New York in Kingston NY.

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