2026 Editor’s Picks: What to Do in the Hudson Valley on May 29 – May 31

This weekend across the Hudson Valley: bees are buzzing, birds are chirping, and life is sprouting everywhere. From orchard food trucks and live music to maker markets, workshops + Pride on the Hudson—something is unfolding in every direction. Hot List below…

ALL WEEKEND 

🌸 Milton, Fri + Sat, The America 250 Agriculture + Arts Jubilee at Prospect Hill Orchards.
A celebration with local artists, food + drink tastings, live music + more! Info HERE.

🛍️ Kingston, Fri – Sun. Field + Supply Spring Market at Hutton Brickyards.
Shop hundreds of curated vendors while enjoying live music, local eats + family-friendly activities at this modern take on the traditional arts-and-crafts market. Info HERE.

🎻 Olivebridge, Fri – Sun. Old Time Rollick at Ashokan Center.
A weekend of fiddle, banjo, guitar, singing + dance workshops for all levels featuring jam sessions, concerts, square dancing + late-night music gatherings. 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, MAY 29 

🌯 Millbrook, 5pm – 8pm, Friday Night Food Trucks at Millbrook Vineyards & Winery.
Summer sunsets on the terrace with food trucks, wine, beer, and live music with Mighty Flynn. Info HERE.

🌿 Highland, 6pm – 10pm. Wild Earth Spring Soirée at Liberty View Farm.
An evening of storytelling, community gathering, wood-fired pizza + desserts supporting equitable access to nature for Hudson Valley youth. Info HERE.

🎉 Newburgh, 7pm. Latin Heritage Celebration at The Ellis.
An evening celebrating Latin heritage with live music from Hudson Valley performers + food from Las Tres Americas. Info HERE.

SATURDAY, MAY 30 

🧚 Kingston, 12pm – 4pm. Hudson Valley Faerie Festival at Forsyth Park.
The Park transforms into a living faerie realm with crowns, storytelling, music, tea, faerie encounters + a magical March of the Faeries finale. Info HERE.

🪕 Woodstock, 12pm – 6pm. Bluegrass Festival at Bearsville Park.
A lively day of bluegrass, local food + drink, artisan vendors + family-friendly fun. Info HERE.

🐝 Hillsdale, 1pm – 3pm. Bees, Herbs & Listening Workshop at Taconic Ridge Farm.
A hands-on, outdoor gathering exploring holistic beekeeping through herbs, hive insights + gentle stewardship with lemon balm tea, honeycomb + pollinator practices. Info HERE.

🍺 Kingston, 1 pm – 6pm. Kest Fest at Kestrel Tavern.
Hudson Valley breweries gather for an afternoon of beer, music, food + community energy. Benefit for Miles of Hope breast cancer charity. Info HERE.

🎵 Stone Ridge, 2pm – 5pm, Handpan Workshop at Whole Sky Yoga.
A beginner-friendly handpan workshop learning history, basic playing techniques, rhythm + groove. No experience needed—instruments provided. More about Whole Sky Yoga HERE. Info HERE.

🌈 Poughkeepsie, 3pm – 10pm. Pride in the Sky at Walkway Over the Hudson.
Kick off Pride season with a Queer Families Festival, flag processions across the bridge + drag and dancing under the stars. Info HERE.

🤲 High Falls, 3pm – 4pm. Healing Through Conversation Series at Intuitively Wild.
A monthly group gathering centered on holistic mental health, each gathering explores a different theme. This month focuses on grief through shared stories, conversation, and grounding practices for reflection, healing, and connection. Learn more about Intuitively Wild HERE. Info HERE.

🎨 Saugerties, 3pm – 5pm. Artist Reception for Nancy Azara + Darla Bjork at OPUS 40.
A special exhibition celebrating the work of feminist artists at the Richards Gallery. Info HERE.

🌕 Wappingers Falls, 6pm – 12am. May Blue Moon Gathering: Creating a Life You Love.
An immersive Full Moon gathering featuring ceremony, live music by Yemanjo and Lester Seal, and a community-centered exploration of sacred connection inspired by Alex Grey and Allyson Grey’s “Anniversary of Knowing.” Info HERE.

✨ Hudson, 7pm. Light Up the Night Benefit Concert at Basilica Hudson.
An intimate living room–style concert with rotating collaborations, storytelling + live performances by Melissa Auf der Maur, Joachim Cooder, Aaron Dessner, Gail Ann Dorsey + more. Info HERE.

🎤 Kingston, 8pm. Michael Kosta at Assembly.
The Emmy Award–winning comedian + host of The Daily Show brings stand-up to Kingston following appearances on late-night TV, Netflix and Comedy Central. Info HERE.

🎶 Bearsville, 8pm. Sea Schulich, Chogi Lama + Friends at Bearsville Theater.
A genre-blending evening of funk, jazz, soul, and New Orleans-inspired grooves led by a world-traveled flutist and composer whose career spans collaborations with legendary artists and iconic stages. Info HERE.

SUNDAY, MAY 31

🗿 Beacon, 10am – 5pm. DIA Beacon Hudson Valley Free Day.
Hudson Valley residents receive free admission to Dia Beacon on the last Sunday of each month. Info HERE.

🍷 Wallkill, 11am – 3:30pm. Sip + Shop Day at Magnanini Winery.
Fine-line tattoos, piercings, permanent jewelry and boutique finds paired with wine and good vibes. Info HERE.

Photo by Field + Supply makers market at Hutton Brickyards in Kingston NY.

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Be sure to visit our Event Calendar HERE for more amazing happenings in the Hudson Valley.

Have a wonderful weekend from Inside+Out Upstate NY!