What to Do in the Hudson Valley This Weekend May 16 – May 18

Looking for a little weekend magic in the Hudson Valley? You’re in luck—this one’s packed with feel-good fun. From Zeppelin-powered rock shows + kites dancing in the sky to flower-filled workshops, Pride celebrations and hearty Sunday suppers—there’s a whole lot to see, do, and savor. The Hudson Valley has something for everyone. Take your pick below…

🍽️ Stone Ridge, Fri May 16th, 5pm – 9pm. ONE Night at Friends and Neighbors.
Friends and Neighbors is hosting an intimate evening of art, community, and connection to celebrate Amanda Russo Rubman’s award-winning sculpture ONE. The event will feature a dinner by Chef Chad Carlson and a live performance by Kelli Scarr, with proceeds benefiting the Woodstock School of Art. Info HERE.

⚡️Kingston, Fri May 16th, 8pm. Zepparella at Assembly.
Zepparella is an all-women Led Zeppelin powerhouse tribute band delivering electrifying, authentic performances with raw intensity. A must see! Info HERE.

🏋️‍♀️ Red Hook, Sat May 17th, 10am – 3pm. Northeast Highlanders Highland Games at Old Rhinebeck Aerodrome.
Watch traditional Highland Games, explore the museum, enjoy local eats + vendors—and don’t miss the chance for a bi-plane ride! Info HERE.

🚘 Athens, Sat May 17th, 11am – 3pm. 6th Annual Sleepy Hollow Lake Classic Car Show at Sleepy Hollow Lake Lodge Parking Lot.
Athens Cultural Center invites car enthusiasts to show off their chrome and horsepower, enjoy delicious eats from local food trucks, and join an iPhone photography workshop to capture the perfect shot—all with free admission for spectators. Info HERE.

🪁 Kingston, Sat May 17th, 11am – 4pm. 2nd Annual Hudson Valley Kite Fest at Kingston Point Beach.
A free, family-friendly event celebrating the simple joy of flying kites. Bring your own or create one on-site. Info HERE.

👙 Pine Hill, Sat May 17th + Sun May 18th, 11am – 4pm. 10th Annual Spring Sale at The Pine Hill Community Center.
Get ready for summer with hundreds of bathing suits, racks of stylish Eileen Fisher, and tons of summer clothes — all at amazing prices. Whether you’re beach-bound or brunch-ready, we’ve got you covered. Don’t miss it — the best pieces go fast! Info HERE.

🛍️ Hudson, Sat May 17th + Sun May 18th, 11am – 5pm. Spring Market at Cannonball Factory.
A new pop-up market with handmade ceramics, holistic skincare, vintage fashion, handmade jewelry, homeware + décor, fresh flowers, original art, outdoor gatherings with live music + delicious food from @yummykitchenny to enjoy! Info HERE.

🪻High Falls, Sat May 17th, 2pm – 5pm. Gathering the Green: “Flower Medicine” at Heartsong Sanctuary.
Hands-on workshop exploring the healing power of flowers through cooking, baking + medicine-making. Info HERE.

🪩 New Lebanon, Sat May 17th, 4pm – 11pm, Fras Fest at The Ruins at Sassafras Farm.
A genre-defying music festival showcasing musicians, bands, DJs + technical artists, food + drink set at the stunning museum. Info HERE.

🎭 Beacon, Sat May 17th, 7pm. Art + Theater at Savage Wonder Art Center.
Experience a night of radical creativity with a visual art show + live performance of “The Bald Soprano.” Info HERE.

🤡 Ellenville, Sat May 17th, 7pm. Borscht Belt Comedy Club at Shadowland Stages.
Comedy night with the only comedian @darryldarryl_ you’ll ever see who’s been lauded by the American Mathematical Society! Info HERE.

❤️‍🩹 Woodstock, Sun May 18th, 10am – 6pm. Healing with Grief – A Day Ritual Retreat at The NEST.
An intimate day retreat where participants honor their sorrows through shared rituals and collective healing, gaining tools to navigate grief as a reflection of love. Info HERE.

🍸 Beacon, Sun May 18th, 12pm – 2pm. The Craft of Gin: Hands-on Workshop at Denning’s Point Distillery.
Join us for a fun and interactive workshop where you’ll learn all about the craft of making gin + leave with your own bespoke bottle! Info HERE.

🍄 Olivebridge, Sun May 18th, 2pm – 4pm. Mushroom Ecology Hike at The Ashokan Center.
Regional mycologist Luke Sarrantonio of Mycophilic leads a guided exploration of local trails, sharing insights into mushroom ecology, foraging tips, and where to find these fascinating fungi. Info HERE.

🥃 Hudson, Sun May 18th, 3pm – 4:30pm. Make Cocktails at Klocke Estate.
Learn (or brush up on) basic cocktail-making techniques and enjoy a Vermouth Spritz, a ‘00’ Sour and a Brandy Manhattan. Info HERE.

🧑‍🍳 Millbrook, Sun May 18th, 3pm – 7pm. Sunday Harvest Dinner at Stonewood Farm.
This intimate, monthly fundraiser features acclaimed chefs, locally sourced meals, and heartfelt community spirit—all supporting the First Harvest Food Pantry + outreach programs. Info HERE.

🌈 Poughkeepsie, Sun May 18th, 3pm – 9pm. Pride in the Sky at Walkway Over the Hudson.

BGHV’s annual celebration returns with festivals on both sides of the bridge, featuring food, drink + fabulous entertainment. 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 Kite Festival at My Kingston Kids 

👉 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!