September Events in Sullivan County
As Labor Day weekend brings summer to a close, Sullivan County shifts from lazy lake days to crisp harvest celebrations—think craft beer under golden canopies, orchards bursting with fresh apples, and cider sipping amidst pumpkin patches. September is one of the most beautiful times to visit the Catskills, and the calendar is full of festivals, markets, and community traditions. Whether you’re here for live music, farm-fresh flavors, or family-friendly fun, there’s something for everyone to enjoy.
🍎 Celebrate the Harvest: Orchards & Cider
Apple Ridge Orchards – Warwick, NY
Open Thursday–Sunday, 9 AM – 6 PM
Apple picking kicks off August 30, with pumpkins ready starting September 20. Visitors can also enjoy a petting zoo, corn maze, and delicious treats like cider donuts and fresh-pressed apple cider.
Soons Orchards & Orchard Hill Cider Mill – New Hampton, NY
U-Pick Apples every weekend beginning Labor Day through late October. Pumpkins start mid-September.
After picking, stop by Orchard Hill’s Tap Room to sample house-made ciders in a cozy farm atmosphere.
Weed Orchards & Winery – Marlboro, NY
Apples & Wine Festival runs September 20–21 and September 27–28, 10 AM – 6 PM.
Enjoy hayrides, live music, apple-themed treats, cider donuts, wine tastings, and family activities from face painting to playground fun.
(Tip: Many orchards are just a short, scenic drive from Sullivan County stays—perfect for a day trip before returning to your cabin or bungalow.)
image from google - Apple Ridge Orchards
🍺 Fall Flavor at Breweries
Catskill Brewery – Livingston Manor, NY
September 1: Open Mic Night with Faith Kelley and Caswyn Moon (6 PM).
September 13: Two Wheels 2 Journey, a motorcycle-friendly community meetup, runs 12–5 PM.
Roscoe Beer Co. – Roscoe, NY
Oktoberfest, September 28 (11 AM – 7 PM): A Catskills favorite! Expect authentic German fare, craft beer, pumpkin carving, hay mazes, woodcarving demos, local vendors, and live music. Costumes are encouraged, making this a festive celebration for families and beer lovers alike.
🎬 Arts, Film & Culture
Big Eddy Film Festival – Narrowsburg, NY
September 25–28
The 14th annual festival at the Tusten Theatre showcases independent films, documentaries, and local talent, along with engaging panel discussions.
Harvest Festival at Bethel Woods – Bethel, NY
Sundays, September 21 & 28, 11 AM – 4 PM
Over 100 regional vendors offer farm produce, artisanal goods, beer, wine, and crafts. Family fun includes hay and corn mazes, a creative learning tent, and live music.
image of narrowsburg from google
🚶 Community, Wellness & Outdoors
Sullivan County Volunteer Firefighters Association Parade – Monticello, NY
September 6, 2 PM
A beloved tradition that begins at the Government Center and parades down Broadway to the firehouse, followed by food, kids’ activities, and evening fireworks at Somerville Field.
Narrowsburg Farmers’ Market – Saturdays, September 6, 13, 20, 27
A vibrant local market behind the Narrowsburg Union, open 10 AM – 1 PM, rain or shine. Stock up on fresh produce, baked goods, and handmade items while mingling with locals.
Pollinator Garden Walk & Birding Hikes – Catskill Visitor Center, Mt. Tremper, NY
Pollinator Walk: September 20, 10 AM – 11:30 AM
Birding Walk: September 26, 10 AM – 11:30 AM
Educational and refreshing, these guided walks are a great way to enjoy the Catskills’ natural beauty.
September in Sullivan County is a season of transition—when warm afternoons meet crisp evenings, and festivals, orchards, and breweries burst with fall energy. From picking your first apple of the season to raising a stein at Oktoberfest, there’s no better time to experience the Catskills.
Plan your stay with Casskell Stays, and make the most of autumn in the mountains.
