What to Do in the Hudson Valley This Weekend Aug 22 – Aug 24

From blooming sunflower fields to county fairs, outdoor concerts + starry-night films, this weekend is a reminder of everything we love about summertime. Always a little something for everyone in the Hudson Valley. Take your pick below…

🎡 Rhinebeck, Fri Aug 22nd – Sun Aug 24th, Dutchess County Fair.
A beloved summer tradition + family-friendly fair that brings together heart-pounding carnival rides, agricultural exhibits, live entertainment, artisan crafts + classic fair foods. Info HERE.

🎻 Olivebridge, Fri Aug 22nd – Sun Aug 24th. The Summer Hoot at Ashokan Center.
Live roots music, a kid-friendly zone, local food + drinks, artisan crafts, gong baths, square dancing, yoga + more! Info HERE.

🎵 Hudson Valley, Fri Aug 22nd – Sun Aug 24th. Door Daze Festival at Rewind, Reason & Ruckkus, Snug Harbor, St Andy’s + The Yard.
A festival highlighting the importance of DIY live music spaces, with Doors At Seven and venues across the Hudson Valley showcasing independent musicians, artists, and creatives.
Info HERE.

🌻 Poughquag, Fri Aug 22nd – Sun Aug 24th, Sunflower Festival at Barton Orchards
Wander 5 acres of 100,000 blooms, ride the carousel, magic shows, live music, petting zoo, unlimited hayrides, craft drinks + more! Info HERE.

🎸 Tivoli, Fri Aug 22nd, 7pm. Jack Grace Band at Traghaven.
Singer-songwriter Jack Grace — once dubbed “that Cash kid, but good” by Jerry Lee Lewis — has spent 25+ years touring, recording, and collaborating with legends from Norah Jones to Merle Haggard, while blending rock, country, jazz, and Latin influences into his ever-evolving sound. Info HERE.

🏴‍☠️ Tuxedo, Sat Aug 23rd + Sun Aug 24th, Pirate Weekend at the Renaissance Faire.
An all-ages celebration of all things nautical + piratical with costumes, contests, games, trivia + more! Info HERE.

🦋 Mount Tremper, Sat Aug 23rd, 10am – 3pm. Pollinator Fest at Catskills Visitor Center.
Celebrate pollinators’ vital role in the Catskills with guided walks, workshops, and hands-on activities for all ages—perfect for gardeners, nature lovers, and the curious alike. Info HERE.

🪘Rosendale, Sat Aug 23rd, 11am – 7pm. The 5th Annual Kirtan Fest at Rail Trail Cafe.
This summer brings chanting under the “cathedral of trees,” with Hudson Valley kirtan leaders and musicians leading a day of song, dance, prayer + community. Info HERE.

🍎 Walden, Sat Aug 23rd, 12pm – 7pm. End of Summer Bash at Angry Orchard Cider House.
Block Party vibes — live music, wood-fired pizza, local food, games, a 360 photobooth + more! Free + family-friendly, no tickets needed. Info HERE.

🦞 Newburgh, Sat Aug 23rd, 1pm – 6pm. Newburgh Seafood Festival on the Waterfront Trail.
Seafood 50+ ways, live music, local vendors + waterfront vibes. Family-friendly fun you won’t want to miss! Info HERE.

🧶 High Falls, Sat Aug 23rd, 1pm – 3pm. Forage + Dye Workshop: Mulberry
Sasha Botanica + Liminal Textiles offer a hands-on, seasonal experience where participants forage local plants, create natural dyes + weave their own fiber art pieces reflecting the colors of the Valley. Info HERE.

🍻 Poughkeepsie, Sat Aug 23rd, 2pm – 10pm. Big Lawn Music Festival at Plan Bee Farm Brewery.
Get ready for a full day of live music, food, and fun—spanning indie, rock, and more—where good vibes, dancing, and community fill the big lawn. Info HERE.

🎶 Saugerties, Sat Aug 23rd, 6pm – 9pm. Rock The Quarry Music Festival at Opus 40.
A new festival pairing the stunning landscape of Opus 40 with many of the region’s most beloved artists, from local legends to rising stars, featuring headliner Gail Ann Dorsey, plus performances by Cindy Cashdollar, Jack Petruzzelli, Simi Stone, Ginger Winn, Kendra McKinley, Jay Collins, Brian Mitchell + more! Info HERE.

🕺 Stone Ridge, Sat Aug 23rd, 7pm – 10pm. The Frolic: A Night of Ecstatic Dance + Connection at the Kiva at MaMA.
The Frolic is a 30-year barefoot, substance-free ecstatic dance welcoming all ages to celebrate freedom, connection + joy with DJ sets, circles of gratitude and the freedom to move however you feel. Info HERE.

🍿 Kingston, Sat Aug 23rd, 7pm – 10:30pm. Summer Film Series: Emerging HV Filmmakers at Artport.
ArtPort  + Cellar Door Cinema Club present the second + final summer screening of short films by local emerging Hudson Valley filmmakers, featuring 8–12 shorts across genres, followed by live Q&A with the creators—come for the films, stay for concessions! Info HERE.

🎤 Kingston, Sat Aug 23rd, 7pm – 11pm. Skorts at Tubby’s.
In less than two years, SKORTS has risen to become one of NYC’s most buzzed-about bands, blending psych-glam, post-alt + dark wave disco, with live shows that have earned them major accolades and press from outlets like Paste + PAPER. 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.

👉 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!