September in the Sullivan Catskills: Events, Fall Fun & Labor Day Weekend Adventures
Summer may be winding down, but September is when the Sullivan Catskills truly begins to come alive.
There’s something special about this in-between season. The warm days linger a little longer, the mornings start to feel crisp, farm stands overflow with the last of summer’s harvest, and the first hints of fall begin to appear across the mountains.
Whether you’re planning a Labor Day escape, visiting for a weekend of live music and local events, or simply looking for an excuse to experience the Catskills before peak fall foliage arrives, there is plenty happening throughout Sullivan County this September.
Here are some of the events and experiences we’re looking forward to this month.
Labor Day Weekend in the Catskills
If you're spending Labor Day Weekend in the Sullivan Catskills, you're in luck. The long weekend offers the perfect opportunity to squeeze in one last summer adventure before welcoming the slower, cozier days of fall.
Labor Day Fireworks
Friday, September 4 | 8:30 PM–9:30 PM
Kick off the long weekend with a little sparkle. A free Labor Day fireworks show will light up the Sullivan Catskills sky on Friday evening at dusk—an especially fun way to start a weekend away with family, friends, or someone special.
Pack a blanket, bring a few snacks, and settle in for one of those classic end-of-summer moments.
Barryville Farmers' Market
Saturday, September 5 | 10 AM–1 PM
Spend your Saturday morning exploring the Barryville Farmers' Market, where you'll find fresh local produce, baked goods, artisan products, handcrafted items, and plenty of Catskills charm.
It's the perfect place to pick up ingredients for a leisurely dinner back at your Casskell Stays home—or simply grab a few treats before heading out for the day's adventures.
Planning a trip?
Among the trees and next to the Delaware River, the Birdsong School house and Juniper Ridge homes are both located in Barryville.
The Schoolhouse is perfect for those seeking a peaceful quiet retreat.
With tons of space, a pool table and game room Juniper Ridge is great for a group of friends or family!
Harvest Festival: The Great Outdoors at Bethel Woods
Sunday, September 6 | 11 AM–4 PM
The fall season officially starts to make its entrance at the Harvest Festival at Bethel Woods.
This Labor Day Weekend edition, themed The Great Outdoors, brings together more than 100 local farm, artisan, and craft vendors along with food, music, family activities, and plenty of opportunities to enjoy the beautiful surroundings of Bethel Woods.
The Harvest Festival runs on Sundays from August 30 through October 4, making it a wonderful September tradition for both first-time visitors and longtime Catskills lovers.
Waterlight Retreat is your ideal home base for Harvest Fest!
Conveniently located right in Bethel, Waterlight Retreat is the perfect stay for a large group looking to enjoy entertainment at Bethel Woods!
Rock the Dock
Sunday, September 6 | 12 PM–4 PM
Looking for one more lakeside summer celebration? Head to Roscoe Mountain Club for Rock the Dock, an afternoon designed for fun, music, and enjoying the final days of summer by the water.
Callicoon Farmers' Market
Sunday, September 6 | 11 AM–2 PM
A Sunday stroll through Callicoon is always a good idea, and the Callicoon Farmers' Market makes it even better.
Browse local farms, food producers, makers, artisans, baked goods, handmade products, and seasonal treats before exploring one of our favorite river towns.
The Gabel Farmhouse is located in Callicoon and near the towns of Jeffersonville and Narrowsburg right on the river. A perfect spot if you are wanting to explore the whole area!
This may be called a ‘Farmhouse’ but you will get nothing but rustic luxury at this gorgeous home!
More September Events to Add to Your Catskills Itinerary
Labor Day Weekend may kick off the month, but September is full of reasons to keep coming back.
BuildFest: Art & Architecture
September 9–13
Bethel Woods will host BuildFest: Art & Architecture, a multi-day celebration centered around creativity, construction, design, and community. The festival culminates in a special Harvest Festival: BuildFest on Sunday, September 13.
John Fogerty & Steve Winwood at Bethel Woods
Sunday, September 13
For music lovers, John Fogerty and Steve Winwood will take the stage at Bethel Woods for an unforgettable evening at one of the Catskills' most iconic venues.
Harvest Festival: BuildFest
Sunday, September 13 | 11 AM–4 PM
The weekly Harvest Festival gets a creative twist with a BuildFest theme, alongside the festival's usual collection of local farms, artisans, crafts, food, music, and family-friendly activities.
Foundation of Funk
Saturday, September 12
Get ready to dance! Foundation of Funk brings good music, good people, and a lively night out to the Sullivan Catskills.
In the Works ~ In the Woods Theatre Festival
September 17–19
For those who love live performance and the arts, the In the Works ~ In the Woods Theatre Festival is a wonderful excuse to spend a September weekend in the Catskills.
Peace, Love, Run Reunion 5K
Saturday, September 19
Lace up your sneakers for the Allyson Whitney Foundation Peace, Love, Run Reunion 5K around beautiful Kauneonga Lake.
With early fall in the air and beautiful Sullivan County scenery all around, this is a great event for visitors looking to add a little movement and community spirit to their weekend.
Harvest Festival: Wellness
Sunday, September 20 | 11 AM–4 PM
Slow down and embrace the more mindful side of the Catskills during Bethel Woods' Wellness-themed Harvest Festival.
Expect local vendors, live music, arts and crafts, and special wellness-focused activities, including sound healing on the historic field.
Big Eddy Film Festival
September 24–27
Film lovers won't want to miss the 15th Annual Big Eddy Film Festival, bringing independent films, storytelling, and creative energy to the Sullivan Catskills.
Don't Miss the Weekly Farmers' Markets
Sometimes the best part of a Catskills weekend isn't a major event—it's a slow morning wandering through a local market with a coffee in hand.
Throughout September, visitors can continue to enjoy favorites like:
Barryville Farmers' Market on Saturdays
Callicoon Farmers' Market on Sundays
Both are wonderful places to discover local food, handmade goods, seasonal produce, and small businesses that make this corner of the Catskills so special.
Make a September Weekend of It
September is one of our favorite times to escape to the Sullivan Catskills.
The summer crowds begin to quiet down, but there is still so much happening. You can spend your morning at a farmers' market, hike or explore the Delaware River, enjoy an afternoon at a local festival, catch live music in the evening, and return to a cozy Casskell Stays property to relax and recharge.
And with fall just around the corner, now is the perfect time to plan your next Catskills getaway.
Whether you're joining us for Labor Day Weekend, a concert at Bethel Woods, a weekend of film and art, or simply a peaceful escape surrounded by nature, September is full of reasons to come experience the Catskills.
Looking for the perfect place to stay while you explore? Browse our collection of unique Catskills homes and start planning your September getaway with Casskell Stays.
