2026 Editor’s Picks: What to Do in the Hudson Valley on Aug 14 – Aug 16

Maybe what we need right now is a little peace + some quality time together. A good weekend to get out and be among people with live music, old-school fairs, riverfront traditions, art, food, dancing and a whole lot of local community character happening across the Valley. Hot List below…

ALL WEEKEND

🕊️ Woodstock, Fri – Sun. 4th Annual Woodstock Festival of Awakening at Bearsville Center + Theater.
Two days + two nights of sacred music, art in the grove, wisdom teachings, movement + community, live music: Nina Rao + Krishna Das + Tribe of Love + Gratefully Yours, awakening talks, Bob Thurman’s Celebration of Life + more. Info HERE.

🎠 Grahamsville, Fri – Sun. 146th Grahamsville Little World’s Fair.
A beloved Sullivan County tradition brings old-fashioned fairground charm, activities, local growers + makers, handmade goods, bakers, artists + plenty of small-town nostalgia. Info HERE.

🎭 Kingston, Fri – Sun. Broadway Theatre Festival at Hutton Brickyards.
Broadway’s greatest hits + brightest stars take over the riverfront with solo shows, tributes, themed performances + nightly Big Shows celebrating the American Songbook + beyond. Info HERE.

🌻 Stone Ridge, Fri – Sun. Sunflower + Sangria Festival at Meadowbrook Farm.
More than 125,000 sunflowers, pick-your-own blooms, hayrides, live music, food, sangria + craft beer, with a farmers market, kids’ activities, vendors + more. Info HERE.

🎭 Saugerties, Fri – Sun. Esopus Creek Puppet Suite at The Tidewater Center.
A beloved summer tradition brings giant puppets, music + community together under the performance tent in a one-of-a-kind spectacle, rain or shine. Info HERE.

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

🦞 New Paltz, Sat + Sun. Annual Seafood + Wine Festival at Robibero Winery.
Fresh seafood, estate wines, specialty cocktails + live music come together for one of the Hudson Valley’s favorite summer traditions. 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, AUG 14

🍷 Hudson, 6pm. Taste of Summer Dinner Party at Whitecliff Vineyard + Winery.
A farm-to-table, family-style three-course dinner paired with award-winning Whitecliff wines, live entertainment + beautiful vineyard views. Info HERE.

⚾ Rhinebeck, 6pm. Old Guard at Old Rhinebeck Aerodrome.
Vintage baseball with antique aircraft museum—and after the game, vintage biplane rides offer the perfect old-school finale. Info HERE.

🎭 Catskill, 7pm. Terrence McNally’s The Lisbon Traviata at Bridge Street Theatre.
A funny, heartbreaking drama about friendship, obsession + unrequited love, set against the heightened emotions of opera and the AIDS crisis. Info HERE.

SATURDAY, AUG 15

🤲 Woodstock, 11am. WAiV’s 22nd Annual Day of Gratitude at the Community Center + Andy Lee Field.
A beloved Woodstock tradition celebrates the volunteers who keep this community going, with a day of gratitude, connection + good old-fashioned community spirit. Info HERE.

🥂 Staatsburg, 12pm. Fizz Fest at Milea Estate Vineyard.
A lively afternoon of sparkling wine, chef-crafted bites, live entertainment + Hudson Valley vineyard views, with estate bubbles ranging from traditional-method bottlings to refreshing seasonal pours. Info HERE.

🎶 Palenville, 1pm. PALENSTOCK at The Griffin House.
A full day of live music, good people + laid-back Catskills vibes, featuring The Sanson Passero Band, Spin Cycle Lava, Pitchfork Malitia, The Charlie Tolmie Band + The Lost Cowboys. Rain or shine. Info HERE.

💃 Kingston, 5pm. Dance Floor Fundraiser at Kestrel Tavern.
Live Latin fusion, a dance lesson + DJ Domo keep the floor moving with Salsa, Bachata, Merengue, Cumbia, Afrobeat + Reggaeton—all supporting TapRoot’s Community Land Trust. 21+ only. Info HERE.

🪩 Hudson, 9pm. After Hours 2026 featuring DJ Kristill Avalanche at the Spiegeltent.
Dance into the night with DJ Kristill Avalanche as Andy Monk’s After Hours series brings late-night beats, queer energy + a packed dance floor to the Spiegeltent. Info HERE.

SUNDAY, AUG 16

🍄 Kingston, 10am. August Foraging Workshop at Wild Hudson Valley Eco Camp.
Head into the woods for a hands-on nature walk exploring seasonal wild edibles + fungi, sustainable gathering, preparation + tasting. Info HERE.

🎙️ Beacon, 11:30am. Third Sunday Concert Series featuring Tara O’Grady on Bannerman Island.
Cruise to the historic island for a self-guided castle tour followed by a live performance from acclaimed singer-songwriter Tara O’Grady. Info HERE.

🌽 Beacon, 12pm. Beacon Sloop Club Corn Festival at Pete + Toshi Seeger Riverfront Park.
A beloved summer tradition celebrates sweet corn, folk music + the Hudson with local food, solar-powered stages + free sails aboard the Woody Guthrie. Info HERE.

🏎️ Kingston, 12pm. Kingston Artists Downhill Derby on Broadway.
Whimsical, gravity-powered sculptures race downhill toward the Rondout in a gloriously weird spectacle of art, ingenuity + chaos. Info HERE.

🎙️ Bethel, 7pm. Brandi Carlile at Bethel Woods Center for the Arts.
Brandi Carlile brings The Human Tour to the legendary grounds, with Jensen McRae opening. Info HERE.

Photo by Vicki Haberski of Cragsmoor Church in Cragsmoor NY. 

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