Uncover the Best Things to Do in the Catskills: Your Upstate New York Adventure Awaits

Venture just 90 minutes north of New York City to discover the serene beauty of the Sullivan Catskills. Renowned for breathtaking mountain views, spirited festivals, rich history, and a delectable farm-to-table dining scene, this lush retreat welcomes all who seek solace from the urban flurry. My adventure companion Howard and I eagerly explored, capturing the essence of New York’s whimsical hamlets through hundreds of photos. Here are the best things to do in the Catskills we found for creating your own unforgettable Catskills story.

Barryville, NY – A Serendipitous Discovery

Our drive through Barryville brought an impromptu pause when the Bang Bang Bar at Stickett Inn beckoned with a vibe we couldn’t resist. While it could have been the place for cocktail stories, had it been open, even just a photo outside the door brings back a smile.

Bethel, NY – Touching History and Art

Bethel is home to none other than the iconic 1969 Woodstock festival site—now a hub for arts at the Bethel Woods Center. Fifty years on, this sanctuary serves not just gigs and learning but is a vibrant museum celebrating the bygone era. 

Wander through the throwback Woodstock exhibits, walk the hallowed festival grounds, and snap playful pictures with vintage props—catch yourself some ’60s spirit!

Fun Fact: Janis Joplin, Jimi Hendrix, Jefferson Airplane, and Joan Baez played at this fantastic concert. 

Don’t miss the charismatic Stray Cat Gallery. Run by the effervescent artist Stacy Cohen, it’s a trove of contemporary art, souvenirs, and tales that Stacy herself may share with you if you catch her on a visit.

Callicoon, NY – A Scenic Gem with History

Picture-perfect Callicoon melds history and scenic backdrops, offering outdoor activities from skiing to river paddling. The Western Hotel, dating back to 1852, adds charm to this picturesque hamlet, which the Delaware River cradles. 

Before you continue, pause at the historic three-arched stone bridge—a photographer’s dream and a fine send-off from this vintage nook.

Glen Spey, NY – A Dash of Eastern Europe in the Catskills

Spiraling through the winding roads of Glen Spey, an unexpected marvel caught our eyes—a stunning wooden church that teleported my friend Howard and me straight back to our Eastern Europe escapades. The spectacular St. Volodymyr Ukrainian Catholic Church commands attention and a respectful U-turn to appreciate its grandeur.

The locals fondly call Glen Spey ‘Little Ukraine,’ and it’s not hard to see why. The strong Ukrainian influence is palpable and beautifully manifested in yet another architectural gem just minutes away—the 1918 Ukrainian Orthodox Church.

Are you craving a sprinkle of mystery? Delve into the eerie allure of the Burn Brae Mansion. Now a quaint Victorian bed and breakfast, this century-old dwelling isn’t just a treat for the eyes—it’s a hotspot for paranormal enthusiasts, boasting ghost stories aplenty. 

Mike Fraysee, the captivating owner, Olympic coach, and former president of the US Cycling Federation, might share a goosebump-inducing tale or two as you explore the grounds and feel the atmosphere thicken with supernatural suspense.

Highland, NY – A Historic Haven

Step back in time at the Minisink Battleground Historical Park, an honorable tribute to the heroes of the Revolutionary War’s Battle of Minisink. Listed on the National Register of Historic Places, this site pairs serenity with education. Meander through the interpretive center and alongside the wildlife that roam the 57-acre memorial.

A stone’s throw away across the state line in Lackawaxen, PA, ventures into the literary world of esteemed Western author Zane Grey, whose museum is perched on the scenic banks.

Livingston Manor, NY – Picturesque and Star-Studded

Outshine your social media peers with a photo or selfie at the Livingston Manor Covered Bridge. Once known as Motts Flat and Vantran Bridge, this picturesque structure crowns the Willowemoc Creek, whisking you back to 1860 and inviting you to bask in its restored splendor.

Swing by some local favorites while you’re soaking up the small-town charm. Gear up for your next adventure at Morgan Outdoors, satisfy your foodie cravings at the upscale Main Street Farm, and toast to the day at Catskill Brewery. You might even bump into the talented Debra Winger, as this haven is her chosen home.

Monticello, NY – Glitz and Nature in Harmony

Resorts World Catskills will astound newcomers with its sheer magnitude and luxury. Nestled in the heart of the Catskill region, this gaming and entertainment behemoth stakes its claim with an 18-story complex teeming with slot machines, table games, and vibrant nightlife. 

The Epicenter hosts enthralling performances year-round, and the suites have direct access to an indoor pool. They’re a stroke of genius for a leisurely escape.

Narrowsburg, NY – Quaint Shops and Coffee Stops

There’s something about Narrowsburg’s darling Main Street that pulls you in. My favorites along this strip are Nest for stylish wear, jewelry, and décor, MayerWasner for chic apparel, and Narrowsburg Proper, my go-to for gourmet treats and a heartwarming brew.

For a meal to remember, The Tusten Cup dishes out tantalizing pasta salads (with fava beans!) and sandwiches that make a simple lunch an event to cherish. Try the iced mocha, which is made with powered premium cocoa. 

North Branch, NY – Chic Elegance & Culinary Delights

The next stop was North Branch Inn, circa 1868. This gorgeously restored inn meshes modern chic with timeless grace. Dine on exquisite farm-to-table marvels like Goat Cheese Ravioli and Dry Aged Ribeye, but leave space for those PB&J Churros that will redefine dessert for you. 

Between mouthfuls, roll a strike in their century-old bowling alley, or relish a stay enveloped in fine linens and upscale comforts amidst the quaint farmland scenery.

Roscoe, NY – For the Love of Trout and Craft

You can’t miss Roscoe’s pride as Trout Town USA. A mecca for anglers, this village, two hours from four states, hosts “in town” treasures and a stretch of five premier trout streams. Beer connoisseurs will relish the chance to savor award-winning brews at Roscoe Beer Co. alongside some hearty pub fare.

Villa Roma Resort – A ‘Dirty Dancing’ Throwback

Experience a Catskills stay that will whisk you back to the Dirty Dancing days of yesteryear. The Villa Roma Resort, echoing the grandeur of those legendary family retreats, is stacked with activities and golfing luxury, complete with breakfast and dinner.

It’s the getaway of the good times, just like the movies promised.

The Catskills Are Calling

I hope my snippets of adventure have sparked your wanderlust. There’s no better time to map your course to this picturesque part of the Empire State. Safe travels, and may the roads lead you to stories worth retelling!

Thanks to the Sullivan Catskills for hosting our travels. As always, opinions and reviews are 100% mine and unbiased. 

Check out more of our New York posts: 

A Winter Getaway to Lake George

Visiting the Lily Dale Assembly

24 Hours at Niagara Falls

To read about the Catskills on Howard’s blog, Backroad Planet.