2026 Editor’s Picks: What to Do in the Hudson Valley on Jun 26 – Jun 28

Upstate Art Weekend leads to a whirlwind of exhibitions, performances, film, music + creative gatherings across the Hudson Valley, with a few non-art gems mixed in. Hot List below…

All Weekend

🎶 Montgomery, Fri + Sat, 8pm. Lyle Lovett: Songs & Stories at City Winery Hudson Valley.
An intimate residency with stripped-down performances, storytelling + surprise setlists featuring classics, deep cuts + special guests. Read more HERE. Tickets HERE.

🎨 Hudson Valley, Fri – Sun. Upstate Art Weekend.
Running June 25 – 29, the region-wide arts festival returns with exhibitions, open studios, special programs + events featuring 160 artists and organizations across the region. Info HERE.

🔥 Hunter, Fri – Sun, 10am – 4pm. Reduction Cooling in “Julia” the Train Kiln at Sugar Maples Center for Creative Arts.
A five-day (June 26 – June 30), hands-on wood-firing ceramics workshop exploring kiln design, firing techniques + reduction cooling for rich iron-red surfaces. Info HERE.

🎭 Woodstock, Fri – Sun, 7:30pm + 2pm. West Side Story at Woodstock Playhouse.
The classic Bernstein + Sondheim musical—a powerful and poignant theatrical story reborn throughout time—staged by the Woodstock Playhouse company. Read more HERE. Tickets HERE.

🍿 Coxsackie, Fri – Sun, 9pm + 11pm. Movies at The Hi-Way Drive-In.
Four separate screens with double features (8 movies). Take your pick! Snack bar + more! Info HERE.

🛍️ Woodstock, Sat + Sun, 9am – 5pm. Mower’s Flea Market.
Antiques, jewelry, Tibetan bowls, vinyl, original art, clothing, boots + hats and more—set in a shady grassy field one block from the town center behind Bread Alone Bakery. Celebrating 49 years, with knowledgeable vendors and plenty to browse. 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 26

🖼️ Kerhonkson, 4pm – 8pm. Artist Reception at Ravenwood.
Nine artists bring painting, sculpture, ceramics, fiber art, and mixed-media works to the barn for an evening of art, conversation, complimentary bubbly, and fireside toasts. Info HERE.

🎶 Annandale-on-Hudson, 8pm. Spiegeltent Opening Night: Underground System at Fisher Center.
The Brooklyn collective blends Afrobeat, punk, funk + disco for a high-energy season-opening dance party. Read more HERE. Tickets HERE.

🌙 Craryville, 8pm. Midsummer Night’s Dream Pride Dance Party at Random Harvest.
A Pride dance party with DJ Friend, costumes encouraged, blending high-energy global club sounds in a playful, magical community gathering. Info HERE.

SATURDAY, JUNE 27

🎉 Woodstock, 12pm – Late. 10-Year Anniversary Celebration at Station Bar & Curio.
Come celebrate their decade of good times, community + unforgettable memories with an all-day celebration featuring a pig roast by Woodstock Meats, live music from Elaris, and a beer tasting with Industrial Arts Brewing. Info HERE.

🎶 Palenville, 1pm. 5th Annual Follow The Arrow Festival at Griffin House.
Hosted by Marco Benevento, this all-day Catskills gathering brings together live music, art, collaboration + community beneath the slopes of Overlook Mountain. Info HERE.

🖌️ New Paltz, 1pm – 3pm. Chinese Brush Painting Workshop at Unison Arts.
Slow down and connect hand, eye, and breath in this mindful introduction to Chinese brush painting with artist Maxine Leu, where expressive ink techniques meet creativity, focus, and calm. Info HERE.

🏳️‍🌈 Kinderhook, 3pm – 5pm. Kinderhook Pride 2026.
The 5th annual LGBTQIA+ celebration of joy, visibility and solidarity in the face of ongoing rights challenges. Info HERE.

🎤 New Windsor, 3:30pm – 6pm. Message from the Mud: A Conversation with Anicka Yi & Rana Dasgupta at Storm King Art Center.
A conversation on interdependence, human and non-human systems + future imaginaries, followed by a prehistoric-inspired culinary experience connected to Yi’s outdoor installation. Info HERE.

🧵 Kingston, 4pm – 7pm. A Woven World Opening Reception at BCMT.
An Upstate Art Weekend exhibition exploring weaving as form and metaphor, featuring works by a diverse group of contemporary artists. Info HERE.

🖼️ Esopus, 6pm – 9pm. Of Frame and Fallow: One-Night Pop-Up Art Show.
A temporary contemporary art activation that transforms a former retail space into a site-responsive exhibition of sculpture, installation, painting, photography, and video. Info HERE.

🎶 Staatsburg, 6:30pm – 7:30pm. SOUND WORKS: Embodied Listening at The Church.
Settle into an evening of guided meditation, sound healing, and deep listening led by Classical Chinese Medicine practitioner Abby Raphel and interdisciplinary artist Ann Burke Daly, whose original sound work anchors this immersive experience. Info HERE.

🎶 Pine Hill, 7pm. AQUARIUS – The 1960s Superband at Pine Hill Community Center.
A night of classic 1960s hits, groovy nostalgia + vintage fashion, with prizes for the best tie-dye, bell-bottoms + flower power looks. Info HERE.

🎉 Hudson, 8:30pm. Shenanigans: Art Omi Summer Opening Afterparty at Pocketbook Hudson.
An Upstate Art Weekend celebration featuring performances, readings + DJ sets marking the opening of Art Omi projects by Nayland Blake and Tschabalala Self. Info HERE.

SUNDAY, JUNE 28

🧑‍🎨 Rhinebeck, 9am. Arts Week at Omega Institute.
A five-day creative gathering (June 28 – July 3) featuring workshops in movement, music, writing + visual arts, with shared meals, events + participant showcases. Info HERE.

🌲 Shandaken, 5pm – 10pm. In the Wild at Foxfire Mountain House.
A candlelit forest dinner experience with tasting hour, multi-course family-style meal + drinks, unfolding in the woods of the Catskills. Read more HERE. Tickets HERE.

Photo by Storm King Art Center— is a 500-acre outdoor museum located in New York’s Hudson Valley, where visitors experience large-scale sculpture and site-specific commissions under open sky.

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