What to Do in the Hudson Valley This Weekend May 2 – May 4

From botanical art + Balkan beats to flea finds, fresh wine and live tunes—this weekend is full of creativity, flavor + springtime energy; something for everyone to enjoy. Take your pick below…

🎨 Accord, Fri May 2nd – Sun May 4th, 10am – 4pm. Drawing Nature Workshop at Hollengold Farm.
Relax + connect with nature in a botanical drawing workshop with @wendyhollender  creating floral illustrations. Info HERE.

🪩 Stone Ridge, Fri May 2nd + Sat May 3rd, 7pm. Rock Academy’s “80s Prom” at High Meadows School.
Open to the public – everyone is invited to the 80s PROM! Guests are encouraged to dress in their most fabulous 80s attire, grab their sweetie and dance the night away. Info HERE.

🎼 Woodstock, Fri May 2nd, 7:30pm, Byrdcliffe First Fridays at Kleinert-James Center.
This monthly concert series features top local talent—this month: Brian Mitchell, Carolyn Marosy + Paul McMahon—in a cozy, art-filled space. Info HERE.

🌳 Hudson Valley, Sat May 3rd. I Love My Park Day!
At I Love My Park Day, New York’s largest statewide volunteer event, join thousands of volunteers in cleaning up parks, planting trees, restoring trails at 25+ Hudson Valley sites, including Olana State Historic Site, Lake Taghkanic State Park, Walkway Over the Hudson, Minnewaska State Park Preserve, Stony Kill Farm, Bannerman Island, Bear Mountain State Park, Harriman State Park + more! Info HERE.

📚 Hudson, Sat May 3rd, 8am – 5pm. Hudson Children’s Book Festival at Columbia-Greene Community College.
World-class authors and illustrators, as well as community organizations, will be in attendance for this free, public event that fosters a love of reading as families meet and greet world-class creators of books for children of all ages. Info HERE.

🛍️ Callicoon, Sat May 3rd + Sun May 4th, 11am – 5pm. Farmhouse Project’s Spring Maker’s Market at Callicoon Hills.
A craft fair, featuring 65+ hand-selected artisans with local food + drink purveyors offering farm-to-table fare, beer, wine + cider. Info HERE.

🌸 Stone Ridge, Sat May 3rd + Sun May 4th, 2pm – late. 29th Annual Spring Wassail at Stone Ridge Orchard.
Traditional folk-style dancing to live Balkan music + feast to celebrate the Celtic Ritual  of spring + the promise of a bountiful harvest! Info HERE.

🎨 Kingston, Sat May 3rd, 3pm – 6pm. “Fracture” Opening Reception at Arts Society of Kingston.
As part of their solo show “FRACTURAL,” the artist invites attendees to participate in an interactive clay-sculpting experience during the opening reception. Info HERE.

🧘‍♀️ Woodstock, Sat May 3rd – Sun May 4th. 4pm – 12pm. When the Sky is Falling, How Do We Catch It? workshops at The NEST.
Join an immersive overnight experience designed for these transformative times. Through Kaleidoscopic Constellations, guided meditation, communal nourishment, ritual + reflective writing, participants will explore two core themes: uncovering the roots of fear + reconnecting with a sense of purpose in the midst of this profound moment in human evolution. Info HERE.

❣️ Kingston, Sat May 3rd, 4pm – 8:30pm. An Evening with Ginger Winn + AJ Yorio at Kingston Carriage House/Maison Apres.
Enjoy cocktails and an intimate performance with two hot musicians, with a dinner at Maison Apres @maison.apres to follow. Info HERE.

🎸 Woodstock, Sat May 3rd, 9:30pm – 11:30pm. DRIP! at Pearl Moon.
This funk-rock-R&B supergroup out of Woodstock blends five standout Hudson Valley musicians for a groove-filled, high-energy set. Info HERE.

🦉 Kingston, Sun May 4th, 9am – 4pm. Red Owl Flea at the Red Owl Collective.
Shoppers can discover antiques, art, books, candles, clothing, decor, handmade goods, jewelry, oddities + vintage treasures from 25+ vendors outside, or inside the 10,000-square-foot vintage shopping space. Info HERE.

🍷 Montgomery, Sun May 4th, 12pm – 5pm. Spring Wine Festival at City Winery Hudson Valley.
The inaugural “Bud Break” Spring Wine Fest offers a full day of new wine releases, accompanied by food pairings, live music, lawn games, outdoor wine garden fun, and exclusive tastings and tours led by the winemaker. Info HERE.

🍎 New Paltz, Sun May 4th, 1pm – 3pm. Sagardotegi Luncheon at Twin Star Orchards.
Indulge in a 4-course lunch honoring the Basque traditions with a bone-in ribeye steak, braised chorizo, potato tortilla, cider catching, + other Basque-inspired classics!⁠ Info HERE.

🎭 Saugerties, Sun May 4th, 1pm – 4pm. Shakespeare’s Pericles at Opus 40.
An epic Shakespearean adventure brought to life by six incredible performers + the wild beauty of the mountains—complete with a fully original score that will transport you! Info HERE.

📚 Mt Tremper, Sun May 4th, 3pm. Poetry reading + Book Signing at James Cox Gallery.
The Gallery is hosting a book signing + poetry reading by Hudson Valley author Guy Reed, coinciding with the final day of the gallery’s current exhibition, “Overlook Mountain,” which showcases photographs of the iconic peak by Kelly Sinclair. Info HERE.

💃 Kingston, Sun May 4th, 3pm – 8pm. Aw Di Body? An African Dance Party at Unicorn Bar.
The Hudson Valley’s favorite African dance party returns for the thawing season with a joyful daytime celebration blending African polyrhythms, queer Sunday church vibes + community healing inspired by the dance floors of Johannesburg and the beaches of Accra. Info HERE.

🎺 Catskill, Sun May 4th, 7:30pm. Upstate Composer Orchestra at Avalon Lounge.
Bobby Previte &+ Michael Kammers bring a 12-piece big band to Avalon the first Sunday of every month. From Strauss to Ellington to Johnny Winter via John Barry. A truly special, must-see event! 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 @wendyhollender

👉 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!