A landscape with trees and a road.

Fall, the Sullivan Way: Festivals, Campfires and Community in the Catskills

Fall That Feels Like Home

In the Sullivan Catskills, fall isn’t about sweater season or pumpkin spice. Branding a season is something that happens in places that need to work for it. Here, fall just works. 

School is back in session. Schedules are juggled around sports practice, dance classes and craft clubs. Weekend plans are made in soccer field parking lots where parents get out of their cars to chat without thumb typing. The sun sets earlier, providing just the right amount of celestial incentive to get things done. 

Meals made from produce purchased at the farmers market serve as leftovers throughout the week because every family made more than one dinner on Sunday afternoon. It’s a time for pot pies and apple crisps. A teaspoon of maple syrup in your morning coffee just to mix it up. 

A farmers market under large white tents features tables with colorful produce and potted flowers. People shop and vendors stand behind tables. Bright flowers are displayed in front; trees and vehicles are visible in the background.

“There’s plenty of things to do year-round, but in fall there’s basically a festival every weekend,” says Shannon Feeney, mom of teens ages 15 and 17, who also works for Roscoe Beer Co. “To me, it’s why this season is THE family time of year. It’s football games, apple picking and Oktoberfest. It’s everything delicious. Especially outside.” 

Downtown on a fall Saturday feels different, a little less bustle and a little more “home.” 

“I live in Roscoe and it’s hard to get too far down Main Street without stopping to talk to a friend. Everyone is out strolling. Some of them in their waders, either on their way to the river or to a café. It’s a site that always makes me smile,” adds Feeney. 

What else would you expect in Trout Town, USA. It’s a time for locals to celebrate the community accomplishments of a busy summer at a pace where no one feels stressed to “get it done before…” insert a summer holiday here. 

“My family goes fishing year-round, but fall is the time where we take it all in and remember how fortunate we are that the river is our community backyard,” says Feeney. 

Fall Campfires & Fish Stories

Like the first fly cast each spring, fall carries its own opening day feel. The air and water temperatures have dipped, which perks fish from the cool bottom of the river to the silky top. A hole you fished in July is very different in September or October. Leaves flit from trees in the breeze, then drift downstream in a kaleidoscope of color. Their shadows hiding hungry brookies and browns below. 

A dirt path winds through a forest with trees displaying vibrant autumn leaves in shades of red, orange, and yellow, sunlight filtering through the branches.

“It’s a slice of wilderness untouched,” says Matt Whitermore, who runs Covered Bridge Campsite just outside of Livingston Manor. “Whether walking through town or on a nearby trail, you’re surrounded by forest preserve. That’s not something you can say about many places. This place is connected to nature.”

Campfires are cozier in fall. Whether enjoying the flame flicker and woodsy smoke smell next to your tent, glamping cabin or from an Adirondack Chair at Upward Brewing Company, everything feels more comfortable. 

“There is no better camping weather than fall in the Catskills,” says Whitermore, who enjoys the immersive and healing practice of forest bathing. “It’s all about being present in the wilderness. Soaking it all in. Understanding that we’re a part of something special and that every moment we get to experience nature is a personal gift, but also one that should be shared.”

Oktoberfest the Catskills Way

Roll into any Catskill community and you’re likely to find a festival or two on any given fall weekend. Oompah bands mix melodies with the slap of beanbags on a cornhole board as kids run between each. Smiles are shared with nods and winks as friends and neighbors toast a summer of hard work with a collective joy of knowing it was all worth it.

A hand holds a glass under a beer tap, filling it with a dark beer topped with a thick, foamy head. The tap is mounted on a rustic wooden wall.

In the Sullivan Catskills, Oktoberfest is both a celebration and a tradition. Roscoe Beer Co. has been hosting their free family-friendly version since 2014. This year, it’s on October 4 and is everything you’d expect and everything you wouldn’t. All of it more fun than you thought you’d have. And if you bob a little too deep into the apple barrel, the brewery hosts a Bloody Mary Brunch the next day. 

For wagon rides with your kiddos, head to Two Farms Brewing in Bloomingburg on October 4th and 5th. After enjoying some German-themed food and drink, you may find yourself participating in a keg toss or stein-holding contest. Lederhosen are optional but encouraged. This festival is also free and features live music each day, plus hot air balloon rides on Saturday. For realsies, advance reservation required.

If you’re looking to sneak away from kids for a day and are age 21 or over, synchronize your Swatches for Saturday, October 4 in Monticello for the 2nd Annual Holiday Mountain Oktoberfest Beer Festival. This historic ski area has been a Catskill destination since it opened in 1957. The rustic venue vibe lends perfectly to the fall festival scene where your entry ticket includes a chairlift ride, souvenir glass and samples from the best of local craft breweries and cider houses in the area. 

Fields, Farms and Flavors

Looking for something a bit more rooted? Hilly Acres Farm Fest on September 27 in Jeffersonville is about making a true agricultural connection with the Catskill landscape. Bring your family to meet the animals, learn from local farmers and take in 4-H and FFA (Future Farmers of America) demonstrations. 

Tall green corn stalks form a dense maze, with a colorful sign in front reading “CORN MAZE” next to an ear of corn. The ground is covered with dry leaves and dirt. The sky is overcast.

At this free family event, kids can paint pumpkins and bounce on a bale during a tractor-pulled hayride, but this fest is all about the food. Hilly Acres is a multi-generational family-owned farm that specialized in raising well cared for beef, pork, lamb, poultry, turkey and eggs. 

Sure, you could pick up their products at the Callicoon or Pleasantville Farmers Markets, but there’s something special about literally buying your beef directly from the farm. 

Art, Film and Autumn Light

From September 25-28, the Delaware Arts Alliance invites you to immerse yourself in a cinematic celebration of cultural possibilities during the Big Eddy Film Festival in Narrowsburg where the newest and best independent films from around the world are screened in restored historic venues built with bricks that date back to the late 1800s. 

On Saturday, October 11th, autumn gets eclectic at the Callicoon Art Walk. Last year, the event showcased 106 artists, musicians and performers including visual arts exhibited at 32 locations throughout the quaint hamlet. It also included 10 musical acts on two stages, three theatre performances, a film screening and two large-scale art installations. Whew!

The all-volunteer events committee says this year is culturally crafted to be something that can only happen by an all-in community effort that can only exist on the banks of the Delaware. 

Peace, Love & Pumpkin Patches

If none of the above dates match your fall schedule, Bethel Woods Center for the Arts gets you. On Sundays through October 5, the lush grounds host local farms and artisans for an annual upstate NY Harvest Festival with live music food trucks, crafts and a whole lot of Catskill culture. 

A large carved pumpkin glows with the words “Peace Love & Pumpkins,” surrounded by several smaller pumpkins on burlap, creating a warm autumn or Halloween scene.

Then, from October 10 through November 2, their historic (and groovy) garden grounds host a Halloween themed Peace, Love & Pumpkins walk-thru experience webbed with thousands of hand-carved jack-o-lanterns and glowing displays of unique pumpkin art haunted by the happy spirit of Woodstock. 

Think Wavy Gravy mixed with dinosaurs, mermaids and witches. Do you see it? Yeah, it’s better to experience it. Maybe even plan your visit so it lands along with one of these other events at Bethel Woods.

  • Friday, October 17 – Murder Mystery Mixer: A Wedding in Transylvania (21+)
  • Wednesday, October 22 – Sensory Friendly Day
  • Friday, October 24 – Friday Night Fright, a haunted walk-thru experience
  • Friday, October 31 – Halloween at Peace, Love & Pumpkins

If this isn’t enough fall fun in the Sullivan Catskills, Cunningham Family Farms in Swan Lake can take your pumpkin spice level to 11 with a corn maze, farmyard games, pick your own pumpkins, gem mining, a hayride and – of course – a hay bale pyramid.  

Find Your Fall in the Sullivan Catskills

Whether you do all or none of these fall festivals, you’ll find an autumn cadence in the Sullivan Catskills that just works. It’s what these communities do, and they do it with an authenticity that can’t be rubber stamped and packed. 

A calm pond reflects trees with vibrant autumn foliage in shades of red, orange, and yellow. Wildflowers and grasses grow along the water’s edge under a bright blue sky.

“Honestly, if all I did was walk down the street and shuffle my feet in the leaves, the sound and feeling would be all I need to get that fall feeling,” says Feeney. 

This is the kind of place where gratification is that simple. Where residents gather during the week to work on a community beautification project and then meet back up in the same spot on the weekend for a festival. It’s as much about what the work did for them as what it does for others. 

When its fall in the Sullivan Catskills, that often includes crockpots, cider donuts and apples as crisp as the 6:30 sunset air. 

Brochure Order Form

To order brochures simply select the check box next to the brochure you would like to order select the quantity and fill out the form below
Select Brochure(Required)
Address
This field is for validation purposes and should be left unchanged.