What to Do in the Hudson Valley This Weekend Jul 18 – Jul 20

Art, music, theater, markets, and splashy fun—this weekend is bursting with local color. Something for everyone. Take your pick below…

🎨 Hudson Valley, Thur Jul 17th – Sun Jul 20th. Upstate Art Weekend in the Hudson Valley.
A vibrant annual celebration of Upstate New York’s culture, UAW returns for its sixth edition, expanding to five days across the Catskills and Hudson Valley. Read more about Helen Toomer and her vision of celebrating art in the Hudson Valley HERE. Event Info HERE.

🫶 Phoenicia, Thurs Jul 17th – Sun Jul 20th. Circle of Creation Retreat at Menla.
A healing retreat for women to reconnect with their feminine essence through ritual, yoga, breathwork, and sisterhood—honoring the womb as a source of creation, renewal + deep inner wisdom. Info HERE.

🪕 Oak Hill, Fri Jul 18th + Sun Jul 20th, Grey Fox Bluegrass Festival.
‘Who’s Who’ of bluegrass, newgrass + roots music! 40 bands on six stages, workshops, family fun, camping, dancing, jamming, foods, crafts + more! Info HERE.

🎸 Woodstock, Fri Jul 18th, 5pm – 7pm. Sabrina + The Gems at Woodstock Pub.
Check out some local original live music in the heart of Woodstock. Info HERE.

🖼️ Woodstock, Fri Jul 18th, 7pm. Opening Reception “Cool/Age” at Queen of Rogues Art Gallery.
New space, new energy! Join their inaugural opening with a special evening featuring a salon-style performance by Sandy Bell, offering an intimate first look at the gallery’s debut exhibition + fresh new home. Info HERE.

🌈 Hunter, Fri Jul 18th, 7pm. 4th Annual LGBTQ+ Midsummer Social at Last Chance Restaurant.
A festive night under the stars with a pre-show reception by West Kill Brewing, a magical outdoor performance of Romeo and Juliet, and a post-show Kiki at Last Chance Cheese with music, dancing + drink specials. Info HERE.

🎭 Rhinebeck, Fri Jul 18th – Sun Jul 20th, 8pm + 3pm. Gypsy at The CENTER for Performing Arts at Rhinebeck.
The musical follows a relentless stage mom as she pushes her daughters in Arthur Laurents’ landmark musical, which explores the gritty world of two-bit showbiz with brass, humor, heart, and sophistication—following a relentless stage mom as she chases stardom for her daughters from vaudeville to burlesque. Info HERE.

🪞 Newburgh, Sat Jul 19th, 9am – 6pm. Flea Market at Newburgh Vintage Emporium.
Find 30+ local makers, vintage dealers, food trucks + hidden treasures, food + more! Info HERE.

💦 Hudson, Sat Jul 19th, 10am – 12pm. Water Wars at FASNY Museum of Firefighting.
Kids can team up with Greenport and local firefighters to try their hand at operating a real fire hose during Water Wars, FREE! Info HERE.

​🎨 Woodstock, Sat Jul 19th + Sun Jul 20th, 11am – 6pm + 10am – 3pm. Art Fair at Woodstock School of Art.
Explore a vibrant showcase of paintings, sculptures, collage, printmaking + more—part of Upstate Art Weekend and packed with incredible local + regional talent! Info HERE.

✈️ Red Hook, Sat Jul 19th + Sun Jul 20th, 12pm. Time Warp at Old Rhinebeck Aerodrome Museum & Air Shows.
Enjoy air shows, museum fun, biplane rides, and a vintage costume contest—beat the heat and join the retro fun! Info HERE.

🎉 Rosendale, Sat Jul 19th + Sun Jul 20th. 12pm – 8pm + 6pm. Rosendale Street Festival.
A grassroots music fest that brings Main Street to life each July with over 100 bands across eight themed stages—celebrating local music, community spirit, and funding scholarships for regional high school seniors. Info HERE.

🦅 Poughkeepsie, Sat Jul 19th, 2:30pm – 3:30pm. Birds of Prey: The Science of Birds in Flight at Mid-Hudson Discovery Museum Pavilion.
Ellen Kalish of Ravensbeard Wildlife Center presents a live raptor program with up-close encounters, rescue stories, and insights into their role in nature—plus a fun bird-themed craft activity for all ages. Info HERE.

🖼️ Hudson, Sat Jul 19th, 3pm – 5pm. A Trifecta Opening Reception at Turley Gallery.
Unveiling three new dynamic solo exhibitions featuring Adam Linn, Vickie Pierre + Sara Stern. Info HERE.

👨‍🎨 Kingston, Sat Jul 19th, 5pm – 8pm. Artist Talk at Kingston Social.
Join artist Brandon Thomas Brown and Princeton Professor Tina Campt for a walk-and-talk, followed by an opening reception with light refreshments. Info HERE.

🎺 Beacon, Sat Jul 19th, 8:30pm – 10pm. Dick Griffin Quartet at Ethan Cohen Gallery.
Legendary trombonist Dick Griffin will perform Sun Ra Ascending, an electrifying tribute to the cosmic jazz icon. Info HERE.

🏖️ East Durham, Sun Jul 20th, 10am – 6pm. Summer Beach Party at Zoom Flume.
Enjoy a day of slides, splashes + lots of smiles while DJ Pat Del cranks up the music and Foam Party! Info HERE.

🖼️ Woodstock, Sun Jul 20th, 2pm – 4pm. Gallery Talk by Bruce Weber at the Historical Society of Woodstock.
Exhibition curator Bruce Weber—an American art historian known for his work on the historic Woodstock art colony—authored the exhibition catalogue and will speak about the group of women artists featured in the show who came to Woodstock in the early twentieth century. 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 The CENTER for Performing Arts at Rhinebeck

👉 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!