An Unplugged Cabins weekend guide — for everyone who’d rather be outside.
TL;DR
~2 hours from Manhattan
- Hudson Valley Irish Festival — Sat, Peekskill riverfront, 11 AM–7 PM
- Rhinebeck Porchfest — Sat, free live music on porches all over town
- Art Walk Kingston — Sat–Sun, open studios and galleries across the city
- Great Jack O’Lantern Blaze — opens Fri in Croton-on-Hudson, 7,000 carved pumpkins
- Angry Orchard 10-Year Anniversary — Sat–Sun in Walden, cider and live music
- Woodstock Festival at Sweet Clover Farm — Sat in Highland Mills, 2–10 PM
- Catoberfest — Sun in Beacon, live music benefiting Mid Hudson Animal Aid
~3 hours from Manhattan
- Adirondack Balloon Festival — Thu–Sun near Glens Falls
- Adirondack Wool & Arts Festival — Sat–Sun, Washington County Fairgrounds
- Sharon Springs Harvest Festival — Sat–Sun
~5 hours from Manhattan
- Bear & Wine Fest — Sat in Speculator, tastings on Lake Pleasant
- Hammondsport Wings & Wheels — Sat, vintage seaplanes and cars
- Red Cat’s Harvest Party at Hazlitt 1852 Vineyards — Sun
- Ithaca Porchfest — Sun, free neighborhood music
- Twilight at Tanglewood — Sat in Elmira, 21+ evening fundraiser
The air is changing. You can feel it. Summer holds on. Fall leans in. And for one weekend, upstate New York belongs to everyone willing to get in the car.
This is the season the region was made for. The light goes gold. The mornings carry a chill that makes coffee taste better. The hills start their slow burn toward October. Two hours north of the city, the Hudson Valley is throwing open its doors — porches, parks, breweries, riverfronts — and inviting you to wander through.
Start Saturday in Rhinebeck, where the whole village becomes a venue. Porchfest turns front lawns and sidewalks into stages. Folk. Jazz. Rock. Singer-songwriters. It’s free. It benefits the library. It is, in the best way, a town showing off.
Or head to Peekskill, where the Irish Festival takes over the riverfront from eleven to seven. Music. Dance. Food. Eight hours of it, with the Hudson glittering behind the stage.
Kingston spends the weekend doing what Kingston does best: making art and opening the doors. Art Walk runs Saturday and Sunday, studios and galleries across three neighborhoods, noon to five. Go. Talk to the artists. Buy something small and carry it home.
When the sun drops, drive to Croton-on-Hudson. The Great Jack O’Lantern Blaze opens Friday night at Van Cortlandt Manor — seven thousand hand-carved pumpkins lit against the dark, a twenty-two-year tradition that somehow gets better every year. It runs through November, but opening weekend has its own electricity.
Sunday slows the tempo. In Beacon, Catoberfest pairs live music with a cause: every pour at Hudson Valley Brewery supports Mid Hudson Animal Aid. Three to seven-thirty. Good music. Good dogs. Good karma.
Willing to drive a little further? The Adirondack Balloon Festival fills the sky over Glens Falls Thursday through Sunday — dozens of balloons rising at once, color against the early-fall green. And at the Washington County Fairgrounds, the Wool & Arts Festival gathers more than a hundred vendors for two days of fiber, craft, food, and sheep shearing. It is exactly as charming as it sounds.
Five hours out, the rewards compound. In Speculator, the Bear & Wine Fest pours New York wines, vodkas, meads, and ciders on the shore of Lake Pleasant, with DEC officers on hand to talk bears. In Hammondsport, vintage seaplanes and classic cars share the waterfront. In Ithaca, Porchfest closes the weekend with free music drifting between the houses.
Here’s the truth. The weekend is short. The drive is the price of admission. And every single one of these is worth the tank of gas.
Unplug. Go north. Come back different.
Planning a longer escape? Our cabin in Hunter, NY sits minutes from Hunter Mountain and Kaaterskill Falls — hot tub, sauna, firepit, and nothing on the schedule. Book your stay.