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bridge into the sunset with the "Upstate Weekend Plans" text written across the photo for the Hudson Valley, NY.

What To Do In The Hudson Valley This Weekend May 19 – May 21

By inside + out | May 18, 2023

Get outdoors for festivals, shopping, food trucks, antiquing & more! The Hudson Valley has magical events for all ages this weekend 🍺 Take your pick below…

🎭 Beacon, Fri May 19th, 9:00 PM. The Vagina Monologues.
An Encore Presentation at the Howland Cultural Center. Info HERE.

🚴 Gardiner, Sat May 20th 7:00 AM. Weekly Group Guide.
Enjoy a scenic ride in a group setting with Raw Endurance, beginning at the Gardiner Library parking lot. Info HERE.

🛍️ Woodstock, Sat May 20th – Sun May 21st. 8:30 AM – 5:00 PM. Mower’s Saturday Opening Market.
Find everything from antiques to zithers to artwork. A treat both for the eye and the pocketbook! Info HERE.

🗿 Saugerties, Sat May 20th, 11:00 AM – 5:30 PM. Community Day.
Come out to Opus 40 to celebrate the local community — free to Hudson Valley residents! A day of visits, tours, music, vendors and more! Info HERE.

🖌️ Shokan, Sat May 20th, 12:00 PM – 5:00 PM. Make It! A Happening at Hinterland.
A day full of engaging hands-on activities, celebrating art, design & nature. Drop into any number of family fun experiences meant to inform & excite your inner creative self, children under 12 are welcome for free. Info HERE.

🧚 New Paltz, Sat May 20th, 1:00 PM – 6:00 PM. Beltane Festival.
A donation-based family-friendly outdoor festival fusing the pomp and whimsy of a Renaissance fair with the magical delights of a springtime picnic gala! Info HERE.

👠 Kingston, Sat May 20th, 6:00 PM – 9:00 PM. HVKC presents PARTY!
Local kink group Hudson Valley Kennel Club (HVKC) presents an evening of food, drink, live performance and crafts for anyone who’s queer and kinky! Drop in for a custom menu by Lekker 209 and a night of pop-up performances and activities! Info HERE.

🤡 Hunter, Sat May 20th, 7:00 PM. Maude Adams Theater Hub presents Comedy in the Catskills.
An evening of stand up comedy at the Doctorow Center for the Arts. Info HERE.

🚶Highland, Sat May 20th – Sun May 21st, 12:00 PM – 5:00 PM. Mayfest Farmers & Makers Market.
Mayfest brings a curated selection of the Hudson Valley’s finest producers including farms, distilleries, breweries, wineries, restaurants, artisans, and more to the Hudson Valley Rail Trail and Walkway Over the Hudson! Info HERE.

🍷 Millbrook Sat May 20th – Sun May 21st, 12:00 PM – 6:00 PM. Food Trucks at Millbrook Winery.
Celebrate the weekend and take advantage of the warm weather with ala carte, family friendly menus from local food trucks
Info HERE.

🥦 Phoenicia, Sun May 21st, 10:00 AM – 2:00 PM. Phoenicia Farmer’s Market.
Spend your Sunday with us at the outdoor market in Phoenicia Behind Phoenicia Supermarket(just off Main Street). Shop with many Spectacular Vendors! Info HERE.

👯‍♀️ Rhinebeck, Sun May 21st, 3:00 PM. The CENTER for Performing Arts at Rhinebeck presents: Hello, Dolly!
It is an irresistible story of the joy of living, aglow with show-stopping song and dance numbers. In the grand tradition of the Broadway musical comedy, Hello, Dolly! is “ guaranteed to bring a smile to every theatergoer’s face, while setting their feet a-tapping.” 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!

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