2026 Editor’s Picks: What to Do in the Hudson Valley on Jun 12 – Jun 14

This weekend across the Hudson Valley moves with Pride, nature, and celebration — from mountain trails and riverfront festivals to late-night music, literary gatherings, and vineyard gatherings. It’s a mix of outdoor connection, community-rooted Pride events, and seasonal celebrations that spill from forests and farms into towns and stages. Hot List below…

ALL WEEKEND 

🎸 Woodstock, Fri + Sat . Grahame Lesh & Daniel Donato at Bearsville Theater.
Two nights of Cosmic Country, jam-driven rock + Americana led by Daniel Donato alongside Grahame Lesh. Info HERE.

📚 Beacon, Fri – Sun. Beacon LitFest.
A weekend literary festival bringing together acclaimed writers, poets, workshops, readings + parties across Beacon. Info HERE.

🪻 New Paltz, Fri – Sun. The Purple Sage Festival at Stone Mountain Farm.
A multi-day music + arts gathering with live performances, workshops, vendors, food + camping under the open sky. Expect an eclectic crowd, late-night energy + a strong sense of community throughout the weekend. Info HERE.

🌲 Hillsdale, Sat + Sun . Zip Tour + Adventure Park Combo at Catamount Mountain Resort.
Full-day mountain adventure combining guided zipline tours with self-paced aerial ropes courses + climbing challenges. 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 12

🍷 Hudson, 6pm. Whitecliff Summer Kickoff Dinner at Whitecliff Vineyard.
Farm-to-table cocktail-style dinner with guided wine pairings, live music + vineyard views celebrating the start of summer. Info HERE.

🏳️‍🌈 Woodstock, 7pm. Jillith Fair: Loving Jill Sobule at Colony Woodstock.
Pride Month tribute concert celebrating Jill Sobule with a wide lineup of musicians + songwriters. Info HERE.

🔥 Beacon, 7pm. Yemanjo at Ecstatic Beacon.
An immersive dance night blending downtempo, organic house + global rhythms with movement workshops + live acoustic sets. Info HERE.

🎭 Woodstock, 7:30pm. West Side Story at Woodstock Playhouse.
The classic Bernstein + Sondheim musical staged by the Woodstock Playhouse company. Info HERE.

SATURDAY, JUNE 13

🐟 Livingston Manor, 10am – 3pm. Livingston Manor Trout Parade on Main Street.
The 20th annual community parade + street celebration featuring floats, booths + trout-themed festivities throughout town. Info HERE.

🍷 Marlboro, 11am – 8pm. Rosé All Day Summer Kickoff Party at Benmarl Winery.
A full weekend of rosé, sunshine + vineyard views celebrating the start of summer at one of the Hudson Valley’s oldest wineries. Info HERE.

🏹 Mount Tremper, 12pm – 3pm. Get Outdoors & Get Together Day at the Catskills Visitor Center.
An inclusive afternoon of outdoor activities with archery, birdwatching, nature crafts, lawn games + a performance by Arm-of-the-Sea Theater. Info HERE.

🥂 Rhinebeck, 12pm. Unhinged Speed Dating at The Kroeg.
An afternoon of fast-paced matchmaking, flirty conversations + mimosas for Hudson Valley singles looking to meet offline. Info HERE.

🖼️ Kingston, 5pm – 8pm. Opening Reception “Putting It Together: Transforming Collage” at 68 Prince Street Gallery.
A group show that surveys collage through an expansive conceptual lens. The show features collage + assemblage works from nearly 50 outstanding artists. Info HERE.

🎶 Accord, 5:30pm. The Wood Brothers at Arrowood Farms.
The Grammy-nominated roots trio brings their blend of soulful folk, blues + Americana to the farm for an outdoor summer show. Info HERE.

🛼 Kingston, 7pm – 11pm. Catskills Roller Disco at SkateTime.
A 21+ roller disco night with house, disco + classic skate anthems, plus costume contests, dance lessons + plenty of retro energy on the rink. Info HERE.

🪘Saugerties, 8pm. The Golden Eras of Jamaican Music: NYC Ska Orchestra at The Local.
Following last year’s sold-out show, the 20-piece orchestra returns with a celebration of ska, rocksteady, reggae + jazz honoring legendary Skatalites percussionist Larry McDonald on his 89th birthday. Info HERE.

SUNDAY, JUNE 14

🍓 Beacon, 12pm – 5pm. Strawberry Festival at Pete & Toshi Seeger Park.
Beacon Sloop Club is hosting a festival, live music, crafts, and a free sail on the Sloop Woody Guthrie. Info HERE.

🍹 Big Indian, 3pm. Tequila Tasting Supper + Spelling Bee at Peekamoose Restaurant & Taproom.
Tequila pairing dinner with small-batch pours, cocktails + an optional community spelling bee fundraiser hosted by Billy Hancock. Info HERE.

🧚 Woodstock, 5:30pm. Pearl Moon Pride After Party with Dust Bowl Faeries.
Keep the Pride celebrations going with the Hudson Valley’s dark cabaret freak-folk ensemble blending gothic polka, circus sounds + woodland magic. Info HERE.

Photo by Sullivan Catskills of the Annual Trout Parade + Festival in Livingston Manor NY.

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Explore our INSIDE+OUT curated Event Calendar for the best of the Hudson Valley’s events. Sign up for our Weekly Newsletter to keep your finger on the pulse of What to Do, Where to Go, and Who to Know.

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