Mohonk Preserve with the "Experience the Hudson Valley" and "Upstate Weekend Plans" text written across the photo.

2026 Editor’s Picks: What to Do in the Hudson Valley on Labor Day Weekend

By Inside+Out | September 2, 2026

Labor Day weekend is here, and the Hudson Valley is sending summer out in style. From hot-air balloons + art fairs to live music, farm fun + festivals, there’s plenty to get out and enjoy. Plus, a gentle reminder that Monday can also be for doing absolutely nothing. Hot List below…

ALL WEEKEND

🎈 LaGrangeville, Fri – Sun, The 35th Annual JP Morgan Chase Hudson Valley Hot-Air Balloon Festival.
Three magical days of colorful hot-air balloons, live music, family fun + stunning views across the Hudson Valley. Info HERE.

🌀 Phoenicia, Fri – Sun. Our Destiny Lies in Our Origins at Menla.
A weekend intensive with Don Oscar Miro-Quesada exploring Andean shamanism, ritual practice, spiritual service + deeper connection with community and the natural world. Info HERE.

🎸 Catskill, Fri – Sun. Dromfest 2026 at Returned Brewing.
Three days of indie rock, art, readings + film spread across walkable downtown Catskill, with an incredible lineup of underground favorites. Info HERE.

🎭 Chatham, Fri – Mon. Commonground Festival at PS21.
A free, family-friendly celebration of contemporary performance + spectacle, with immersive installations, live music, dance, food trucks, apple picking, lawn games + more across PS21’s beautiful grounds. Info HERE.

🌳 Modena, Fri – Mon. Community Connections Weekend at Hurds Family Farm.
The final day of a four-day celebration connecting visitors with local farms, artisans, nonprofits + community organizations, with seasonal farm activities happening throughout the day. Info HERE.

🎨 New Paltz, Sat – Mon. Woodstock-New Paltz Art & Crafts Fair at the Ulster County Fairgrounds.
Hundreds of talented makers, handcrafted art, jewelry, home goods + specialty foods, with live music 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, SEP 4

🛍️ Catskill, 9am. Catskill First Fridays.
An all-day community celebration with extended shop hours, pop-ups, music, specials, and plenty of sips and snacks throughout town. Info HERE.

🎆 Staatsburg, 6:30pm. Concert on the Great Lawn + Fireworks Display at Staatsburg State Historic Site.
Kick off Labor Day weekend with live music on the Hudson Riverfront lawn, followed by fireworks over the river. Bring a blanket or lawn chair; free admission. Info HERE.

🎹 Woodstock, 8pm. Marco Benevento with very special guest Dave Dreiwitz at Maverick Concert Hall.
A night of adventurous piano-driven music from Marco Benevento, joined by longtime Ween bassist Dave Dreiwitz, in Maverick’s magical Music in the Woods setting. Info HERE.

🎶 Beacon, 8pm. Guthrie’s Ghost + Guy Davis at Towne Crier Cafe.
A Labor Day weekend tradition at the Towne Crier, pairing Guthrie’s Ghost’s rootsy tribute to Woody Guthrie with bluesman Guy Davis. Info HERE.

SATURDAY, SEP 5

🍅 Accord, 1pm. Tomato Fest at Hudson Valley Seed Co.
A celebration of peak tomato season with tastings, seed-saving demos, garden tours, crafts, music, food, vendors + plenty of garden goodness. Free admission, with some activities at an additional cost. Info HERE.

🎧 Tivoli, 1pm. Labor Day Weekend All-Vinyl DJ Set with DJ Pete Pop at Lasting Joy Brewery.
Spend the afternoon with a soundtrack of all-vinyl favorites, plus beer, food + a laid-back last-weekend-of-summer vibe. Info HERE.

🎨 Woodstock, 2pm. Woodstock Monoprint Invitational Exhibition + Auction at Woodstock School of Art.
A showcase of contemporary monoprints created in the School’s graphics studio, with an afternoon reception + auction supporting the school and local artists. Info HERE.

🤘 Wappingers Falls, 2pm. GR8 Hudson Valley Hard Rock Fest at Heritage Financial Park.
A full day of hard rock, metalcore, hardcore, punk + alternative music with a stacked lineup of bands. Info HERE.

🎨 Kingston, 3pm. September Gallery Openings at Arts Society of Kingston.
Three new exhibitions open at once: Iceland By 4, Echoes of the Ancestral by Elisa Pritzker + Poetry of the Ordinary, bringing photography, contemporary art + work from ASK members together under one roof. Free admission. Info HERE.

🎸 Woodstock, 8pm. Big Deep: The First Show at Bearsville Theater Lounge.
Be among the first to experience Woodstock’s newest quartet as Big Deep makes its hometown debut with an immersive evening of original music, improvisation + cinematic soundscapes. Info HERE.

SUNDAY, SEP 6

🦉Kingston, 10am. Red Owl Flea at Red Owl Collective.
First Sundays every month through October: hunt for treasure with 20+ vintage sellers, local makers, antique dealers, upcyclers, pickers, collectors, food + more! Info HERE.

🌻 Fleischmanns, 11am. Village Fest at The Print House.
A lively little Labor Day weekend street fair with live music all day, local food + craft vendors, art and activations at village shops. Info HERE.

☘️ Kingston, 11:30am. Hooley on the Hudson at T.R. Gallo Memorial Park.
Three stages of live Celtic music, Irish step dancing, food + craft vendors and family activities at one of Kingston’s biggest waterfront celebrations. Info HERE.

🎶 Woodstock, Sun, 7pm. Talkin’ Hard Work – A Woody Guthrie Labor Day Tribute at Colony Woodstock.
A foot-stomping Labor Day tribute to Woody Guthrie, with full-band renditions, folk songs, working-class anthems + sing-alongs. Info HERE.

LABOR DAY, SEP 7

We also recommend taking a walk in nature, going fishing, sticking your feet in a local stream, or reading a book on the couch. You deserve it! HAPPY LABOR DAY OFF!