2026 Editor’s Picks: What to Do in the Hudson Valley on Jun 5 – Jun 7

Summer starts breaking through the Hudson Valley this weekend — Pride moves through towns, vineyards come alive, art unfolds in unexpected places, and nights stretch a little longer than usual. Hot List below…

ALL WEEKEND 

🖼️ Woodstock, Fri 5pm – 8pm + Sun 1pm. Spring Art Auction Preview Party + Online Auction at James Cox Gallery.
A Friday evening preview party kicks off this online auction featuring paintings, drawings, New Yorker cartoons + collectible works tied to Woodstock’s artistic legacy. Info HERE

🌙 Sleepy Hollow, Fri + Sat 8:30pm. The Hill: Stories From Spoon River at Sleepy Hollow Cemetery.
A lantern-lit walking performance based on Edgar Lee Masters’ Spoon River Anthology, guiding audiences through the cemetery to hear stories of a small town’s lives, secrets + legacies told among the headstones. Info HERE.

🏳️‍⚧️ Hunter, Fri–Sun. Mountaintop Pride at Scribner’s Lodge.
A full weekend Pride celebration with DJ sets, pop-ups, food + cocktails from guest takeovers, plus activities like flash tattoos, flower bar, crafts + local vendors throughout the property. A relaxed, community-focused kickoff to summer in the mountains. Info HERE.

🎨 Rhinebeck, Sat + Sun 10am. Rhinebeck Crafts Festival 2026 at Dutchess County Fairgrounds.
A curated weekend market featuring handmade goods, specialty foods, craft demos + family activities, with a wide mix of artists and makers from across the region. Info HERE.

🍷 Marlboro, Sat + Sun 11am – 5pm. Sangria Fest at Weed Orchards & Winery.
A full weekend on the farm with sangria tastings, live music by Cuboricua, food from the kitchen + a relaxed, family- and dog-friendly setup. Tastings include a keepsake glass + pours, with general admission also available onsite. Info HERE.

🦋 Warwick, Sat + Sun 12pm – 5:30pm. Pollinator Festival at Warwick Valley Winery & Distillery.
A weekend focused on pollinators + native plants with live music, artisan market, British car show, environmental groups, garden demos + a native plant sale supporting monarch conservation efforts. Info HERE.

🍷 New Paltz, Sat + Sun 11am – 6pm. Robibero Rosé Party at Robibero Winery.
A two-weekend celebration in the vineyard with handcrafted rosé, pink cocktails, live music + wood-fired pizza. Relax among the vines with golden hour views—pink attire encouraged. Walk-in only, no reservations needed. Family + pet friendly. Info HERE.

🍄‍🟫 Hudson Valley, ALL weekend! Your Ultimate Guide to the Hudson Valley’s Vibrant Farmers Markets: Spring to Fall.
Your go-to guide to the Hudson Valley’s vibrant Farmers Markets, spring through fall—where fresh seasonal produce, local farms and community come together. Info HERE.

FRIDAY, JUNE 5

🛸 Pine Bush, 10am – 4pm. Pine Bush UFO Fair on Main Street.
A free, family-friendly street fair celebrating the hamlet’s reputation as the “UFO Capital of the East Coast” with costumes, live music, food trucks, alien-themed vendors + plenty of local UFO lore woven throughout the day. Info HERE.

🍳 Beacon, 3pm – 7pm. Eat Drink Beacon Food Crawl on Main Street.
A walkable one-mile food crawl featuring small bites + sip stops hosted by participating restaurants and shops, highlighting the flavors and energy of Beacon’s Main Street. Info HERE.

🪊 Kerhonkson, 7pm. First Fridays Music Series at Rough Cut Brewing.
Catch an evening of live jazz-rock grooves under the summer sky as Pour La Terre brings their improvisational jam energy to the backyard stage. Cold pours, good vibes + music that keeps the night moving. Info HERE.

🎷 Saugerties, 7pm – 10:45pm. Sonny Rollins: Saxophone Colossus Film Screening + Conversation at Opus 40.
A special screening of Robert Mugge’s documentary on jazz legend Sonny Rollins, followed by a discussion with the filmmaker, biographer Aidan Levy + former Opus 40 Artistic Director Tad Richards. Presented with Upstate Films. Info HERE.

🎻 Chatham, 7:30pm – 9pm. The Next Festival of Emerging Artists at PS21.
Grammy-nominated cellist Andrea Casarrubios joins emerging musicians for a program of new works by women immigrant composers, featuring world premieres + a newly commissioned double concerto for cello, percussion + strings. Info HERE.

SATURDAY, JUNE 6

🤖 Hudson, Sat 12pm–1:30pm. The AGI Transition: How AI Affects Work and Life at Spark of Hudson.
A free, beginner-friendly workshop exploring what artificial general intelligence is, how it’s already reshaping jobs + daily life, and what this shift could mean for the near future. Includes demos + open discussion. Info HERE.

🏳️‍🌈 Kingston, Sat 12pm – 5pm. Hudson Valley Pride March & Kingston Pride Festival 2026 at Academy Green.
A full day of Pride kicking off with a community march from uptown Kingston into a festival at Academy Green featuring music, vendors, local orgs + celebrations of LGBTQ+ community. Festivities continue with after-parties across Kingston. Info HERE.

🌿 Ghent, 2:30pm – 4pm. What’s Out There Weekend at Art Omi.
Free expert-led landscape tour hosted by the Cultural Landscape Foundation exploring the hidden design history of parks, gardens + open spaces led by Jeremy Adams. Info HERE.

⛵ Hudson, 6pm + 7:30pm. Handel Sets Sail aboard the Schooner Apollonia.
An intimate sunset sail on the Hudson River featuring soprano Meredith Wohlgemuth with musicians from early music ensemble Ruckus, offering a close-up encounter with Handel performed on the water. Info HERE.

🦄 Kingston, 9pm – 1am. AUTHENTIC: The Kingston Pride Party at Unicorn Bar.
A late-night Pride celebration with DJs Tryst + Michael Vadacchino bringing high-energy dance sets, raw emotion + deep club vibes in a space centered on authenticity, expression + community. Info HERE.

SUNDAY, JUNE 7

🌈 Red Hook, 11am. Red Hook Youth Pride Parade + Festival.
A youth-led Pride parade and community celebration organized by local young leaders to keep Pride visible and active in town during a period of transition. A call for community support and participation. Info HERE.

🏳️‍⚧️ New Paltz, 12pm–5pm. New Paltz Pride March & Festival at Hasbrouck Park.
The 22nd annual celebration of LGBTQ+ visibility, joy + community featuring a march, festival programming + local gathering in the park. Info HERE.

Photo of “Pride in the Sky” at Walkway Over the Hudson event hosted by Big Gay Hudson Valley—founded in 2008 by Stephan Hengst and Patrick W. Decker, Big Gay Hudson Valley connects and celebrates LGBTQ+ communities across the Mid-Hudson Valley through local businesses, events, resources, and community initiatives.

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