The greatest joy of a three-day getaway often lives in the unexpected.
A unique gift discovered at a shop you hadn’t planned to visit. A wine tasting that becomes a porch conversation over a shared bottle. A mental photograph captured, then revisited when you return to see the same place in a different season.
The Sullivan Catskills region is full of what Bob Ross would call “happy accidents.”
Take the Barryville Oasis, for example. Yes, it’s a gas station. But it’s also a bodega and karaoke bar that serves a damn good Bloody Mary at brunch. Local filmmaker Drue Penella will tell you more about gems like the Oasis as he and other locals fill your three days with the tips and tricks that make a Sullivan Catskills getaway iconic.
Adventure Needs a Good Night’s Sleep
The first step in planning a trip to the Sullivan Catskills is booking a bed, so let’s start there. This is a place where you settle in, breathe a little slower and remember what it’s like to be somewhere real. It’s a feeling that starts with colorful welcome mats, tent zippers to the trees and all sorts of different front doors. Each has its own story that begins with the wholesome people who live here and decided to share the experience with you.
Where to Stay
- At Unique Escapes, you can sleep in a dome under the stars.
- Climb into a treehouse at the Chatwal Lodge.
- Choose the Steam, Soak, Drink or Eat themed room at the quirkily quaint Stickett Inn.
- Hit the jackpot at Resorts World.
- Splash around with your kids at Kartrite Resort — which happens to have the largest indoor water park in New York.
- Spoil yourself at something a bit more elegant like The DeBruce.
Your cozy cabin, streamside farmhouse or modern bungalow is waiting here.
Day 1: Adventures in Charcuterie
Now that you’re settled in, it’s time to spend a day treasure hunting. But first, coffee.
Morning: Catskills Coffee Lodge
Catskills Coffee Lodge sits just upstream from The DeBruce along the historic Willowemoc Creek in Roscoe, housed in the reinvented brick and mortar of an old NAPA Auto Parts building. Here, you’ll find deliciously curated coffees and teas along with decadent baked goods, including house-made cookies. For a little extra kick to bring home, pick up an 8-oz jar of their signature Habanero Pepper Jelly.
Midday: Callicoon Marketplace
From there, pop over to the Callicoon Marketplace. In this community space, you’ll find both permanent businesses and rotating pop-ups ranging from food to fiber to furniture. A highlight of the marketplace is the Callicoon Pantry, which features a literal wall of nuts — cashews, pistachios, pecans, hazels, and such.
“I make personal excuses to stop there when traveling in that area,” says Drue Penella, who lives nearly an hour away in Claryville. “I tell people that the wall of nuts is a must-see. It would be one thing if this was a stand-alone store, but what makes it unique is how it shouldn’t fit amongst the other businesses in the marketplace yet does so perfectly.”
Local Tip: If you happen to hit the Callicoon Marketplace in the afternoon, a stop at nearby Seminary Hill Orchard & Cidery is a very good idea. Especially in fall.
Afternoon: Sullivan Sundries
From there, take the scenic drive along County Road 164 to Sullivan Sundries in Jeffersonville. Locally known as the “Sundies,” this open and sunny space was once home to the Jeffersonville Hardware Store. Today it houses Bloom Coffee and R52 Home, which offers a distinctive mix of old and new items including books, clothing, Catskill antiques and a collection of greeting cards that needs to be experienced in person to understand and appreciate.
Anchoring the store is the owners’ — David Conison, Rebecca Moyer and Brian Sutton — love of food. Specifically, a global selection of cheese, spices, meats, sauces, snacks and condiments.
“The last time I was there, I walked out with like five different hats, a few bricks of cheese, three jars of olives and a cappuccino,” says Drue, adding that discovering places like Sundies helps him develop a new relationship with being local. “It’s different each time. Here, your old staple is never old.”
More Day 1 Options
Drue also recommends La Salumina in Hurleyville and Van Smokey in Livingston Manor. La Salumina is a butcher shop that’s only open Friday and Saturday because owners Eleanor Friedman and Gianpiero Pepe are prepping products for the rest of the week.
At Van Smokey, you can snag all sorts of goods from the meat market, stay for dinner and enjoy a plate of smoked gouda mac or choose from a selection of deliciously spiced tacos. Maybe end the day at Smokey.
Day 2: Get Up & Outside
Morning: Fuel Up
If you’re staying at Resorts World or Kartrite Resort in Monticello, start the day at the Monticello Bagel Bakery. The name says it all, but a bit of schmear plus a sammie to go will perfectly set the tone for a day outside.
Midday: Roosa Gap Fire Tower
The beauty of the Catskills will cleanse your soul on its own, but it’s best to go for the deep cleanse and immerse yourself in the wonder of the landscape. Dan Hurst knows a little bit about that. He’s been living here for, well, his entire life and still describes his home as a hidden treasure.
“To really get a sense of this place, you’ve got to get above it,” says Dan. “The Roosa Gap Fire Tower in Wurtsboro is the perfect place to do just that.”
A mild hike up and along the stunning Shawangunk Ridge will bring you to the only remaining fire tower in the Sullivan Catskills. From there, on a clear day, the naked eye can see 40 miles in any direction.
“If you’re a birder, this is the place to be during migration season,” adds Dan. “You’ll feel like you’re sitting in an air traffic control tower – only nature’s on the radio conducting a feathered symphony.”
Afternoon: Bashakill Wildlife Management Area
For a more relaxed outing — or a bonus after a morning hike — don’t miss the Bashakill Wildlife Management Area, which happens to be just down the road. Here, you can rent a kayak at the Mamakating Environmental Education Center (MEEC) and go for a paddle, drop a line in the water or take a cruise on the Mamakating Rail Trail, a non-motorized recreational corridor which borders the Bashakill Wildlife Management Area and extends 14.1 miles.
Local tip: Make a bonus stop at Bashakill Vineyards, which stores its wine and offers tastings in a custom-built wine cave — an experience unto itself.
Day 3: Get Hippie & Relive History
Visit Bethel Woods
There is only one town in the world that can say it hosted the most culturally shifting and legendary music festival in history. That town is Bethel Woods, where half a million people gathered in 1969 for the Woodstock Music and Arts Festival.
Despite the lore of the festival, the site wasn’t much of anything until 1996 when Alan Gerry — a longtime resident of nearby Liberty and founder of Cablevision Industries — decided to change that and purchased the original 37-acre festival site. Today, it has expanded to an 800-acre experience of music and cultural history that includes a 15,000-seat outdoor concert venue, a 1,000-seat terrace stage, and an intimate 400-seat indoor hall.
It also includes the Museum at Bethel Woods, a world-class interactive museum that showcases the 1960s in a way that transports visitors to a decade and place where the world changed.
“Bethel Woods is one of those must-see places. Not just in America, but in the world,” says Dan. “I can’t even count how many times I’ve been there, but each has been transformative. To this day, I cannot fathom how a community this small did something that big.”
Let It All Unfold
Back at the Barryville Oasis, the disco ball just started spinning. Owner Johnny Pizzolato — who also happens to be the Town Supervisor, co-owner of Stickett Inn and Stickett Inn Cider, plus co-host of Barryvilleradio.com — is about to kick off an upstate New York dance party.
It’s your last day in town, so you dive right in. It’s only one more margarita and besides, you need some more time to plan your next escape to the Sullivan Catskills.
By now, you’ve learned that this is the kind of place that unfolds — and unless you let it happen, you’ll miss the genuine vision, creative passion and honest acceptance that accidentally made the past three days some of the best of your life.
What’s a few more hours?