What to Do in the Hudson Valley This Weekend Aug 29 – Sep 1

This Labor Day weekend, the Hudson Valley comes alive with hot air balloons, live music, theater, art festivals, climbing, camping, and community celebrations—offering something special for everyone. Take your pick below…

🎨 Phoenicia, Aug 29th – Sep 1st, Phoenicia Festival of the Arts in Phoenicia.
This five-day festival transforms Phoenicia with gallery shows, outdoor art, performances, artisan markets, a free community mini golf course, workshops, family activities, live music, film + more! Read more HERE.

🎈 Lagrangeville, Fri Aug 29th – Sun Aug 31st, Hudson Valley Hot Air Balloon Festival at Tymore Park.
Plan your next photo-op as some 75 hot-air balloons paint the sky in a rainbow of colors—or schedule a tethered or full flight of your own. Fireworks, helicopter rides, live music, food trucks + family activities add to the fun! Info HERE.

🪔 Phoenicia, Fri Aug 29th – Sun Aug 31st. Journeys of Discovery: Shamanic Life Lessons at Menla.
Two lifelong friends, Alberto Villoldo and Robert Thurman, weave South American and Tibetan wisdom into an intimate program of dialogue, ceremony, and practice—guiding participants to reconnect with nature, explore mind and body beyond belief systems, and leave with tools for healing and self-discovery. Info HERE.

💫 Ellenville, Fri Aug 29th, 8pm. Opening Night of DARKER THE NIGHT/ BRIGHTER THE STARS at Shadowland Stages.
John Cariani’s newest play, set in northern Maine during the Perseid Meteor Showers, unfolds in a series of short stories about love, hope, wishes + connection. Info HERE.

🎹 Woodstock, Fri Aug 29th, 8pm – 10pm. Marco Benevento + Dave Dreiwitz at Maverick Concert Hall.
A benefit concert of fearless jams, deep grooves + genre-bending magic in support of Woodstock’s Maverick Concerts. Info HERE.

⛲️ Stormville, Sat Apr 30th + Sun Apr 31st, 8am – 4pm. Stormville Airport Antique Show & Flea Market.
Shop 400+ vendors with antiques, vintage goods, handmade crafts, and more—plus enjoy tasty bites from local food spots. Info HERE.

🧗‍♂️ New Paltz, Sat Aug 30th + Sun Aug 31st. 8am – 10pm. 4th Annual Gunkfest at the Center at Stone Mountain Farm.
Gunks Climbing Film Festival, clinics + more. A rock climber’s dream! Info HERE.

🖼️ New Paltz, Sat Aug 30th – Mon Sep 1st, 10am. Woodstock-New Paltz Art & Crafts Fair at Ulster County Fairgrounds.
Featuring 200+ artists from across the country, plus a children’s tent, hands-on crafts + live entertainment. Info HERE.

👢 Bearsville, Sat Aug 30th, 12pm – late. The 2nd annual Labor Day Honky Tonk at Tinker Tavern.
Vintage vendors, country 2-step dancing + live music together for a lively celebration. Info HERE.

🍅 Accord, Sat Aug 30th, 1pm – 4pm. Tomato Fest at Hudson Valley Seed Co.
The first annual Tomato Festival celebrates summer’s harvest with wine + food tastings, cooking demos, garden tours, hands-on activities + family-friendly fun. Info HERE.

🤸‍♀️Chatham, Sat Aug 30th + Sun Aug 31st, 1:30pm + 5pm. Commonground Festival at PS21.
France’s @cie.basinga “Soka Tira Osoa”—a participatory tightrope performance with live music that blurs the line between audience + performer. Info HERE.

🏕️ Kingston, Sat Aug 30th + Sun Aug 31st, 2pm + 11am. Labor Day Campout at Seed Song Farm.
Live music, acoustic jams, a bonfire—pack your tent, bring an instrument + join the campout! Info HERE.

🍏 Milton, Sat Aug 30th, 2pm – 9pm. Locust Grove Music Festival.
A day of music from 7 bands, food trucks, cidery + more! Info HERE.

🗿 Tivoli, Sat Aug 30th, 3pm – 7pm. Art Walk With Visual Arts Curator & Artists at Kaatsbaan Cultural Park.
An Art Walk with curator Hilary Greene, exhibiting artists, and the Lachaise Foundation’s Paula Hornbostel, offering a special chance to explore contemporary Hudson Valley works alongside bronze sculptures by Gaston Lachaise. Info HERE.

🎶 Bearsville, Sat Aug 30th – Mon Sep 1st. 7pm – Late. Feat Fest at Bearsville Theater.
Little Feat and Friends, with special guests Larry Campbell & Teresa Williams, Charlie Starr, and Robert Randolph, bring three nights of legendary funk and rock to Bearsville Theater in Woodstock. Info HERE.

🎧 Lexington, Sun Aug 31st, 10am – 4pm. Record Fair at Van Dusen’s.
Connecting music lovers, collectors + outdoor enthusiasts with confirmed dealers like Sepiatone, DJ Whippoorwill/Electromagnetic Radio, Basement32, Jitterbug, Roundabout, Sweet Side + Mountaintop Records—plus an afterparty around the fire pit. Info HERE.

🥳 Fleischmanns, Sun Aug 31st, 10am – 6pm. Village Fest!
Filling Main street with music, food, art and fun! Info HERE.

☘️ Kingston, Sun Aug 31st, 11:30am – 8pm. The 25th Annual Hooley on the Hudson at TR Gallo Memorial Park.
Three stages of live music, dance, vendors + family fun—starts with a parade + opening ceremony. Free! Info HERE.

🌈 Athens, Sun Aug 31st, 8pm. River Glow at the River Garden.
Celebrate the end of summer at the River Garden with Michele Vreeland, live music, and dazzling kaleidoscope projections over the Hudson by @bamiam. Info HERE.

🚜 Explore Hudson Valley’s vibrant SPRING to FALL Farmers Markets, Marketplaces, and Community-Shared Agriculture (CSA).
Support small local farms, foster a sense of community and promote healthy living. From live entertainment to family-friendly activities, they offer a fun and diverse experience for all! Info HERE.

Photo by HV Hot Air Balloon Festival

👉 Know of more cool events happening in the Hudson Valley/Catskills area?
Leave them in the comments below.

Have a wonderful weekend from Inside+Out Upstate NY!