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Local Events | Alive with Possibilities

Here, fields turn into stages, barns into galleries and nights into soundscapes that echo with every beat of Woodstock’s legacy. Discover a local maker, enjoy farm-fresh harvests or connect with community like a local. These featured Sullivan Catskills events put you right where you need to be.

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Upcoming Events

Reel Good Thursdays

Where: Hurleyville Art Center
When: January 22 @ 6:00 pm
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Aerial Yoga

Where: Mountaindale Yoga
When: January 22 @ 6:00 pm
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Trivia Night

Where: The Woodstock Way
When: January 22 @ 6:00 pm
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Paint and Sip!

Where: Roscoe Beer Co
When: January 22 @ 6:00 pm
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Trivia Night at Rafters Tavern

Where: Rafters Tavern
When: January 22 @ 6:30 pm
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Tavern On Main: Trivia Night!

Where: Tavern on Main
When: January 22 @ 6:30 pm
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Mat Pilates With Aly Steigart

Where:
When: January 23 @ 9:30 am
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Friday Fitness Series Winter 2025 – 2026

Where: Cornell Cooperative Extension
When: January 23 @ 10:00 am
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Callicoon Crafters

Where: Callicoon Brewing Company
When: January 23 @ 5:00 pm
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There’s always a reason to gather

It’s one of those “good problems”. Finding a week without a festival or parade in Sullivan County is nearly impossible, and no one’s complaining. This is a place that celebrates everything. From music to maple syrup and trout to tractors, there’s always a reason to come together, raise a glass and cheer for the good things in life big and small.

You might catch a Fourth of July parade winding through a village green or stumble into a delightfully quirky National Alpaca Day celebration, complete with an alpaca costume contest (yes, really). That’s the beauty of the Catskills where every community adds its own creative twist to tradition.

Go green!

The Irish spirit runs deep here, especially in Jeffersonville, where the Ancient Order of Hibernians has been marching downtown for generations. The streets fill with laughter, fiddles and the unmistakable skirl of bagpipes as residents paint the town green. And just as one parade wraps up, another begins a few towns over, each with its own local flair, stories and shared joy. From dawn to dusk, it’s a day-long chorus of camaraderie and cheer.

Trout & tractors

You don’t have to look far to find trout or tractors in the Catskills as both come with celebrations worthy of their legacy.

In Livingston Manor, the Annual Trout Parade has been making waves for more than 20 years. This community celebration—2025’s theme was Saturday Trout Fever—is affectionately called “the best day of the year.” And it’s more than just fun: proceeds go directly to local food pantries and the Livingston Manor Central School music program.

Down the road in Callicoon, the Tractor Parade has been rolling strong for over three decades. More than 200 tractors, from vintage showpieces to modern marvels, chug proudly through Main Street before ending with a homegrown community BBQ that only Callicoon could pull off. 

Leaf-peeping parties

Nature steals the show year-round, but never more so than in autumn, when Sullivan County’s hills burst into color and the whole county turns into a celebration of harvest and home.

Oktoberfests fill the air with music and malt, farmers markets overflow with the season’s best and every town seems to have its own version of a pumpkin patch party. But the crown jewel of fall might just be the Bethel Woods Harvest Festival, which runs through the entire month of September. With local farms, artisans, food trucks and live music set against the backdrop of Woodstock’s legendary grounds, it’s an unforgettable Catskills weekend getaway—just two hours from New York City.

A place that loves a good time

In Sullivan County, celebration is the occasion. Whether you come for the parades, the colors or the company, you’ll find yourself swept up in the rhythm of a place that truly knows how to live, laugh and gather.

Make time for what matters.
Reserve your getaway now.

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