Locals will be the first to tell you that fall in the Catskills is the real hiking season. There is simply nothing that can compare to the sublime experience of leaf peeping while peak bagging. It’s the sound of your favorite boots shuffling through fresh fallen leaves, the rich smell of a balsam-filled forest, and the vivid color of red maple and chestnut oak peppered among green pitch pine in every direction.
Some describe fall foliage as fruity pebble season. To us, it’s a hug from a friend. It’s a conversation that began over a fresh coffee and was never finished because no one wants that warm feeling to end.
In Sullivan Catskills, it doesn’t have to be because it’s the kind of place where you remember a conversation with the local baker more than any of the images you forgot to share on your phone. It’s a place of grit and warmth, where everything feels and tastes like nowhere else. Like the baker’s story, the cider donut you “couldn’t say no to” was crafted and shared right here.
Pick a hiking trail. Pick one that those trusty boots have walked a dozen times. Choose a peak you’ve heard about but never got around to hiking. Or come without a plan. In the Sullivan Catskills, the most memorable itineraries are those that happen because the local outfitter said, “I know what you should do.” Their advice will be spot on and likely pique your curiosity in a way that makes you have to figure out which experience will have to be shelved until your next visit.
So, what are you waiting for? Pull on your warm sweater, knock yesterday’s dirt off your boots and let’s get around to writing stories together in the Sullivan Catskills.
Leaf Peeping by Boot & Bike
There is nothing more accessible than a stress-free autumn walk or bike ride on the O&W Rail Trail connecting Parksville, Liberty, Ferndale, Hurleyville, South Fallsburg, Woodridge and Mountain Dale. There is also nothing more that embodies the honest hand-built spirit of community than the history of the former New York, Ontario and Western Railway corridor.
What began as an idea over a beer in the 1980s, has over decades been cultivated into a gentle recreational trail that connects historic rail towns. Like each section of the trail, these, now trail towns, have a story and character of their own. Put simply, there’s a reason the local brewery in Liberty is called Bridge and Tunnel.
If up (and down) is more your person-powered speed, Walnut Mountain Park features 13 miles of hiking and mountain biking trails on 265 pristine acres. It’s also home to Walnut Mountain, the second highest peak in Sullivan County. But first (wink), when it comes to the sweeping panoramic views you will brag share with your siblings on social media.
Scenic Drives & Americana “Sighs”
Of course, you’ve got to get there somehow. “There” is up to you, but the route is the Upper Delaware Scenic Byway. This 70-mile country roll is enveloped by scenic vistas, bold rock formations and charismatic small towns that naturally soften the limestone and shale ridges of the byway.
Roll down the windows, lean your motorcycle into a curve that screams “whee” along with you and soak in the Americana bliss of a winding road where the iconic views are called Hawk’s Nest and Ten Mile River. You may also want to bring your favorite boots. From nearly every roadside vista is a bonus hike featuring no-biggie-thingies like a Stone Arch Bridge constructed in 1875.
Taste Sullivan Catskills, One Sip at a Time
Fall mornings in the Sullivan Catskills are better when they start with a carefully crafted and sometimes artfully frothy beverage from a cozy coffee shop. Cruise over to Bloom Coffee’s Insta and peek at a photo of the Witches’ Familiar to get a sense of both. Step two is to set your nav for 4890 NY-52 in Jeffersonville.
Just remember, life here isn’t overcaffeinated, it’s about slow-living and taking the time to taste every layer of flavor while having a conversation with folks like Jeannine and Jessica England, sisters and owners of Catskills Coffee Lodge in Roscoe. Their breakfast and lunch menu is like nothing you’ve seen or tasted before. Neither is their signature Habanero Pepper Jelly that you’ll pick up along with a few sweet treats before heading out the door. Oh, and fun fact, you will NEVER guess this unbelievably cozy and comfortable stop along the banks of the historic Willowemoc Creek used to be a NAPA Auto Parts.
That’s the charm of this special place. It’s honest and self-reliant. The kind of place where you see the character, wit and true craftsmanship in everything. It’s vintage shops next to a fire hall where the annual chicken bar-b-que is treated like a community holiday.
Farm-to-Pint
It’s places like Two Farms Brewing where the lavender and hops that are grown on-site provide the inspiration and ingredients for their farm-to-glass brews. The brewery also just happens to be in the middle of a peculiarly lush forest where the sugar maples provide that special Sullivan Catskills sweetness to a few of the brews.
If craft beer is your thing, Upward Brewing Company can satisfy your hop habit along with dinner after hiking “Beer Mountain,” a trail on the property that gives incredible panoramas of the Catskill Mountains. It’s a scene that can also be experienced while sipping one of their beers that was carefully created with Catskill Mountain spring water. And yes, they taste better while sitting around one of the brewery’s outdoor campfires overlooking a glassy pond.
Cider with a View
For those who crave a crisp fall cider, nearby Seminary Hill Orchard & Cidery in Callicoon is the kind of place where your eyes will get big, then immediately think “imagine getting married here” and you can. You can also stay there. The orchard’s Boarding House is two historic homes with apartments featuring one to four bedrooms. The touches of each are a story themselves thanks to Homestedt, the local studio who outfitted the apartments with Kilim rugs, luxury WRIGHT mattresses and soft linen sheets. Each also features at least one private bathroom, many with restored vintage white clawfoot tubs.
Fall Fresh Experiences
Since by now you’ve decided to stay a few days in the Sullivan Catskills, you might as well take in a fall festival. Every Sunday from August 31 to October 5, Bethel Woods Center for the Arts hosts its Harvest Festival with over 100 local farm, artisan and craft vendors. There’s also wagon rides, a corn maze, live music and food trucks.
Located on the grounds of the 1969 Woodstock Music and Arts Festival, it should surprise no one that Bethel Woods hosts Peace, Love and Pumpkins from October 10 through November 2. During this walking experience though garden trails, you will however, be surprised by witches, dinosaurs and mermaids that come to life in the form of hand-carved jack-o-lanterns. Special nights include a Sensory Friendly Show, Murder Mystery Mixer, Friday Night Fright and a Halloween Trunk or Treat.
Logging, Lumberjacks & Layer Cake
For a little more local history and flavor (read baking contest and yes, a beard and mustache competition), do not miss the Narrowsburg Logging Days on October 5. This free, family fun event also features the New York State Lumberjack Association Lumberjack Contest where many of the participants will also enter the beard and mustache contest.
Pick-Your-Own Moments
Of course, no fall fresh experience in the Sullivan Catskills is complete without a farm visit. Majestic Farm in Mountain Dale is the spot for picking 100% organic apples. Whether you pluck them from the tree yourself or grab a bushel from the farm store, there is something indescribable about the first crunch of a crisp fall apple.
If your farm team includes a van full of kids, Cunningham Family Farms in nearby Swan Lake is a place where giant checkers and chutes and ladders are the opening act for pick your own pumpkins, hayrides, gem mining and – because it’s the Sullivan Catskills – a hay bale pyramid.
What else would you expect from a place whose artistic legacy ripples through every quirky gallery, fun and funky restaurant menu, and in every welcoming voice of the people who live and work here. It’s a perfect place where the cheers from a little league game echo with the kind of hometown pride that makes visitors want to twist their rally cap and hop in the home team bleachers.
A Place Where Stories Stick
Sure, this is a story about fall, but the Sullivan Catskills story isn’t seasonal. Whether the trees are sugary with snow, it was a good year for boiling sap, the fish are biting at a secret hole, or the leaves are just about to hit peak color, the story drifts through its historic main streets and into the shops and restaurants where friends tell each other they should get together again soon. The difference here is they always do.
