What to Do in the Hudson Valley This Weekend May 23 – May 26

Looking for family-friendly fun this Memorial Day Weekend? From farm tours, comedy and art fairs to live music, local markets +  community festivals, there’s something for everyone to enjoy in the Hudson Valley! Take your pick below…

🎼 Olivebridge, Fri May 23rd – Mon May 26th. Ukulele Weekend at The Ashokan Center.
Get ready to strum, sing + soak up the aloha spirit at the ultimate music + dance camp for uke lovers of all levels! Info HERE.

🤡 New Paltz, Fri May 23rd, 6pm – 9:15pm + 9:30pm. 4th Fridays at Water Street Market + Comedy Series at Denizen Theatre.
Fourth Fridays at Water Street returns monthly for community gatherings featuring local food, conversation and a comedy series showcasing rising stars from NYC + beyond. Info HERE.

🎭 Woodstock, Fri May 23rd, 7pm. Performing Arts of Woodstock presents “The Flick” at Woodstock Community Center.
The Pulitzer Prize + Obie Award-winning play is a hilarious and heart-rending cry for authenticity in a rapidly changing world. Info HERE.

👢Woodstock, Fri May 23rd, 6pm – 9pm. Honky Tonk Happy Hour at Station Bar & Curio.
Live music with First Rodeo and Strawberry Runners + Kissing Well. Plus, happy hour pricing ‘til 9pm! Info HERE.

⛲️ Stormville, Sat May 24th + Sun May 25th, 8am – 4pm. Stormville Airport Antique Show & Flea Market.
Shop 400+ vendors with antiques, vintage goods, handmade crafts + more—plus enjoy tasty bites from local food spots. Info HERE.

👩‍🌾 Saugerties, Sat May 24th, 9am – 2pm. Annual Open House + Farm Stand Opening at White Feather Farm.
Tour the farm, check out biochar demos, enjoy food + drink, kids activities, fresh veggies + more! Info HERE.

🖼️ New Paltz, Sat May 24th – Mon May 26th, 10am – 5pm. Woodstock-New Paltz Art + Crafts Fairs at Ulster County Fairgrounds.
Over 200+ artists + makers, live demos, food + drink, kids activities + more! Info HERE.

🕰️ Rhinebeck, Sat May 24th + Sun May 25th, 11am – 4pm. Barn Star’s Spring Antiques at Dutchess County Fairgrounds.
125 indoor exhibitors with Americana, folk art, antique jewelry, mid-century modern, home + garden décor + more. Info HERE.

🍷 Chatham, Sat May 24th + Sun May 25th, 11am – 5pm. Hudson-Berkshire Wine & Food Fest at Columbia County Fairgrounds.
Enjoy a day of sipping on local wines and browsing unique handmade crafts! Info HERE.

🛍️ Hudson, Sat May 24th + Sun May 25th, 11am – 5pm. Spring Market at Cannonball Factory.
Shop handmade goods, vintage finds, original art, hear live music + enjoy eats from @yummykitchenny. Info HERE.

👨‍🌾 Poughkeepsie, Sat May 24th – Mon May 26th, 12pm – 5pm. Mayfest Farmers + Makers Market at Waryas Park.
This vibrant outdoor market features local farmers, artisans and makers offering fresh produce, handmade goods, live music, food trucks + family-friendly fun. Info HERE.

🪕 Bearsville, Sat May 24th, 1pm – 6pm. Bearsville Bluegrass Festival at Bearsville Center Park.
Kick off the weekend with bluegrass, local food, Phoenicia Flea + good vibes. Info HERE.

🪂 Gardiner, Sat May 24th, 4pm – 10pm. Gratefully Yours Family Picnic at Skydive The Ranch.
Listen to your favorite live Grateful Dead cover songs and picnic at the Ranch—BYO coolers, drinks + food, chairs, blankets + more! Info HERE.

🏃‍♂️ Kingston, Sun May 25th, 8am – 11am. The Woodstock Races 5K and 15K  at the Zena Elementary School.
The Onteora Runners Club hosts a scenic + challenging 15k and 5k races on the country roads bordering Woodstock, NY. Info HERE.

🇺🇸 Fleischmanns, Sun May 25th, 10am – 4pm. Annual Memorial Street Fair.
Live music, local vendors, food + drink, family fun + more! Info HERE.

🍶 Hyde Park, Sun May 25th, 12pm – 4pm. Traditional Japanese Yakitori event at Dassai Blue Sake Brewery.
Grilling season kick-off—yakitori-style, featuring grilled chicken, cold sake, fresh sushi, live music + open sake brewery tours—no tickets or reservations required. Info HERE.

👠 Saugerties, Sun May 25th, 1pm – 4pm. Burlesque Drawing Café with Tryst La Noir at Jane St. Art Center.
A creative fusion of art + performance with themed costumes + music. Info HERE.

👩‍🎨 Fleischmanns, Sun May 25th, 5pm – 9pm. Women Rising Festival at Arts Inn.
An incredible evening of female-led performances from flamenco to blues, Shakespeare to indie-pop. The show will have a little something for everyone. Info HERE.

💃 Woodstock, Sun May 25th, 7pm. Hudson Valley Flyers at Colony Woodstock.
Two-steps, waltzes + western swing from the 1930s–’50s—perfect for dancing or just hanging out. 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 White Feather Farm

👉 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!