What to Do in the Hudson Valley This Weekend Aug 1 – Aug 3

Looking for something fun, fresh or fabulously weird this weekend? From county fair thrills to drag comedy-musicals, cheese tastings, spooky midsummer vibes and treasure hunting at a vintage flea—there’s a little something for everyone in the Hudson Valley. Take your pick below…

🎡 New Paltz, Fri Aug 1st – Sun Aug 3rd. Ulster County Fair at Ulster County Fairgrounds.
A classic summer celebration with midway rides, live music, ag exhibits + family fun! Info HERE.

🍻 Catskill, Fri Aug 1st – Sun Aug 3rd, 4pm – 6pm. The 3rd Annual Subversive Summerfest at Subversive Malt & Brewing.
Their throwback party returns for a full weekend of summer fun with lobster rolls + fish fry cookout, specials, live music + good vibes all around. Info HERE.

🧀 Hudson, Fri Aug 1st, 5:30pm – 7:30pm. Bloomy Cheese Tasting Class at Neverstill Wines.
A guided wine + cheese tasting with Jessica Galen of @bloomydobbs, spotlighting woman-made cheeses, NYS wines + cheese myths decoded.. Info HERE.

🎶 Woodstock, Fri Aug 1st, 6pm – 9pm. Jerry Garcia’s Birthday Bash at Colony Woodstock.
Gratefully Yours honors Jerry’s legacy with a high-energy Grateful Dead tribute on the Garden Stage. Info HERE.

🎻 Saugerties, Fri Aug 1st, 6:30pm – 9pm. Sunset Concerts at Tina Chorvas Park.
Enjoy a free outdoor Sunset Concert featuring Kevnnell + the Hardwoods, a dynamic trio blending original songs, traditional fiddle tunes and unique covers with strings + electronic wind instruments—perfect for a relaxed evening with lawn chairs, blankets, and live music by the water. Info HERE.

🎭 Phoenicia, Fri Aug 1st – Sun Aug 3rd. 7pm + 2pm. Bye Bye Birdie at Phoenicia Playhouse.
A fun-filled musical comedy for all ages! Follow rock star Conrad Birdie’s wild visit to Sweet Apple, Ohio in this high-energy show packed with classic songs, hometown talent + plenty of laughs. Info HERE.

💃 Annandale-on-Hudson, Fri Aug 1st + Sat Aug 2nd, 8pm till late. Jackie & Jan’s Joyride! at Bard’s Spiegeltent.
A glitter-fueled musical road trip with NYC drag stars Jackie Cox + Jan Sport—full of songs, chaos + campy detours. Info HERE.

🚠 Hunter, Sat Aug 2nd + Sun Aug 3rd, 10am – 4pm. Scenic Skyride at Hunter Mountain.
Ride the Kaatskill Flyer to the summit of Hunter Mountain for one of the best views in the Catskills. On clear days, you’ll spot peaks stretching into Massachusetts and Vermont. Info HERE.

🥾 Woodstock, Sat Aug 2nd, 12pm – 2pm. A Journey Through Geological Time with Woodstock Land Conservancy.
Join renowned geologist Robert Titus for a guided walk through Sloan Gorge, exploring the ancient forces that shaped its landscape—from deep seas to glaciers and tectonic shifts. Info HERE.

🏖️ East Durham, Sat Aug 2nd, 1pm – 3pm. Superhero Day at Zoom Flume.
Meet Spider-Man + friends for high-fives, photo ops + a day of slides, splashes + smiles! Info HERE.

🖼️ Shady, Sat Aug 2nd, 2pm – 5pm. Opening Reception at Elena Zang Gallery.
Join them at Elena Zang Gallery for the opening reception of Mary Frank’s “Horizons,” an exhibit showcasing evocative works that push creative boundaries. Info HERE.

👺 Beacon, Sat Aug 2nd, 5pm – 11pm. Cirque Du Creep at The Yard.
A MIDSOMMAR SCREAM! 50+ artists + vendors, food trucks, live music, sideshows, flash tattoos + spooky fun.Info HERE.

💃 Hudson, Sat Aug 2nd, 7pm – 11pm. Escaper at Park Theater Hudson.
Escaper is a NYC-based band known for their sci-fi dance parties + genre-blending mix of funky jams + progressive psych-rock, powered by a dynamic lineup with deep roots in the Northeast jam scene. Info HERE.

🦉Kingston, Sun Aug 3rd, 9am – 4pm. Red Owl Flea.
First Sundays every month through November 2nd—hunt for treasure with 20+ vintage sellers, local makers, antique dealers, upcyclers, pickers, collectors, food + more! Info HERE.

🦆 Gardiner, Sun Aug 3rd, 12pm – 5:30pm. Whitecliff Vegan Market at Whitecliff Vineyard.
Support @woodstocksanctuary with a special day in Gardiner featuring vegan vendors, award-winning wine, and a tasting flight where all proceeds go to animals. Info HERE.

🚜 Explore Hudson Valley’s vibrant SPRING to FALL Farmers Markets, Marketplaces, and Community-Shared Agriculture (CSA).
Support small local farms, foster a sense of community and promote healthy living. From live entertainment to family-friendly activities, they offer a fun and diverse experience for all! Info HERE.

Photo by Red Owl Flea + Collective

👉 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!