Things To Do in the Catskills: New York’s Quaint Hamlets

(UPDATED JULY 2022) Driving north of New York City about 90 minutes brings you to the Sullivan Catskills of New York. This well-known area is famous for magnificent mountain views, festivals, history, and farm-to-table cuisine. It is an upscale retreat for those wishing to escape the hustle and bustle of the city. My travel-mate and friend Howard of Backroad Planet and I began our trip in the Catskills by exploring the quaint region as we drove countless miles and took hundreds of photos. Here are some cool suggestions for awesome things to do in the Catskills, separated into hamlets.

Bethel, NY

Located at the site of the 1969 Woodstock festival is the Bethel Woods Center for the Arts. This beautiful outdoor venue is the site that the famous rock festival was held 50 years ago. Today, it poses as a music venue, learning center, and museum.

After touring the Woodstock exhibits, be sure to wander the grounds and see where the festival took place. A memorial/dedication plaque lists the performers who graced the Woodstock stage. Looking straight ahead from the memorial, you can see the concrete marker where the stage once stood. We loved taking cheesy photos with the dress-up props and boarding the hippie bus for the footage of the festival.

After leaving Bethel Woods, pop into Stray Cat Gallery, an art gallery chock full of treasures, owned by dynamic artist Stacy Cohen. Browse exquisite contemporary art pieces by New York artists as well as a host of Woodstock souvenirs and apparel. If Stacy is there, ask her to tell you about her Woodstock experience. Her stories are almost as great as the cool framed artwork and unique items for sell in her shop. 

North Branch, NY

A fantastic farm-to-table meal and more is what you’ll get from North Branch Inn, a newly restored inn done in modern, yet timeless elegance. Enjoy farm-to-fork cuisine, such as Goat Cheese Ravioli, Dry Aged Ribeye, and Cauliflower Salad, but be sure to save room for the PB&J Churros.

While waiting for your food, bowl a few games in the 100-year-old bowling alley within the restaurant. You can also stay at the North Branch Inn (circa 1868) which showcases royal linens, luxurious amenities, and high-end toiletries, positioned in a the rolling farmland of Catskills. 

Roscoe, NY

I came across the adorable Trout Town USA sign and quickly detoured for a visit to the village of Roscoe. A two-hour drive from four states, Roscoe touts the claim of being home to five of America’s best trout streams. This angler’s paradise has a small strip of businesses “in town” to see, but most of all great scenery and a fisherman’s dream.

You may also want to check out the award-winning craft beverages at Roscoe Beer Co., also great for pub food. 

Callicoon, NY

Callicoon is another precious Sullivan Catskills area that looks like a vintage postcard scene to me. The town offers a rich railroad history, gorgeous scenic areas, and has many outdoor opportunities such as skiing, hiking, and paddling. My favorite thing was the Western Hotel, a circa 1852 western bar, supper club, and inn in Callicoon on the Delaware. I would have loved to stay there!

Callicoon runs along an admirable section of the Delaware River, along New York and Pennsylvania. Don’t miss the amazing three-arched stone bridge, circa 1873, that spans Callicoon Creek before you leave. These Instagram-worthy gold spots are few and far between. 

The Catskills are famous for a hotel experience like no other, or one you might recall from the Dirty Dancing movie. Like many New Yorkers, guests traveled upstate to stay in these all-inclusive “Dirty Dancing era” resorts that include a plethora of activities and world-class golf. Villa Roma Resort is where family-friendly and offers plenty to do to keep everyone in your party entertained and happy during your visit. Breakfast and dinner are included. 

Narrowsburg, NY

I fell in love with the quinessential small town of Narrowsburg. The downtown is so adorable and filled with cute little locally-owned shops on Main Street. The shops I recommend are Nest (clothing, accessories, jewelry, and home decor), Mayer Wasner (ladies’ apparel), and Narrowsburg Proper, a specialty food shop. I had a delicious coffee drink at Narrowsburg Proper and brought home some locally-made gourmet kitchen items and a cookbook. 

While in Narrowsburg, enjoy a fresh salad or perfectly prepared sandwich from The Tusten Cup. The side order of pasta salad (with fava beans) that accompanies the sandwiches even outshines the tasty main course. Tusten Cup has delicious coffee and tea drinks, as well. I loved their iced mocha, made with powered premium cocoa. 

Glen Spey, NY

Driving along the curvy, country roads of Glen Spey and boom, Howard and I saw this amazing wooden church that immediately took us to back to our Eastern Europe travels. The St. Volodymyr Ukrainian Catholic Church certainly made us do a U-turn and come back. We loved admiring the grand architecture.

Due to the influx of Ukrainians in Glen Spey, the area is often referred to as “Little Ukraine” because it reminded them of their country. Minutes down the road was a second impressive church, the 1918 Ukranian Orthodox Church. 

Looking for a good ghost story or even a fright? I love to visit haunted locations and the Burn Brae Mansion delivered one for the books. This century-old Victorian bed and breakfast along the Delaware River is owned and run by Mike Fraysee, a most-interesting man (Olympic bicycling coach who was also president of the US Cycling Federation) who shared first-hand stories about the ghost sightings at the mansion. We also toured the estate.

I felt the air thicken as we walked down the hall where many of the occurrences have taken place on the second floor. Paranormal activities are no strangers to Burn Brae. Besides the frights and stories, Burn Brae Mansion is a beautiful place to visit and learn about. 

Barryville, NY 

While driving through Barryville, alongside the Delaware River, Howard and I ran into a  cute little place that we couldn’t resist. The sign on the door introduced us to the Bang Bang Bar at the Stickett Inn.

We had to take a photo there, but unfortunately the Bang Bang Bar was closed at that time of day. Of our whole trip, this was the saddest moment because we knew how cool it would have been to sip cocktails at the cozy retro bar. Fresh rose cocktails are highly recommended. The inn offers four wooded suites with luxury amenities. 

Livingston Manor, NY 

Have a photo shoot at the beautiful the Livingston Manor Covered Bridge, a bridge that beckons to be the star of your social media feed. It was previously called both the Motts Flat and Vantran Bridge, spanning the Willowemoc Creek. The gorgeous covered bridge was built in 1860 and restored to its grandeur in 1984.

While in town, visit Morgan Outdoors (a great outfitter), Main Street Farm (upscale market, grocery, coffee shop, and cafe), and the Catskill Brewery. You may even run into actress Debra Winger, who calls Livingston Manor home. 

Highland, NY

The Minisink Battleground Historical Park is listed on the National Register of Historic Places. It is dedicated to the brave men fought and died at the Battle of Minisink, a major Revolutionary War battle in the Upper Delaware area. The park has an interpretive center that explains the areas of the park, while skittish wildlife wander the expansive 57-acre grounds.

While in the area, you may also choose to visit the Zane Grey (American westerns author) Museum over in Lackawaxen, PA. 

Monticello, NY

I nearly croaked at the sheer size when we pulled up to the mammoth property known as Resorts World Catskills in the heart of the Catskill region. This 18-story 7 billion dollar luxury casino offers 100,000 square feet of gaming action (2150 slot machines and 150 table games), as well as 10 onsite bars and restaurants. A 2,500 seat Epicenter entertainment complex offers year-round musical performances. A portion of the casino is dedicated to Chinese-themed table, card, and dice games.

Resorts World Catskills has all-suite hotel rooms but I recommend one that leads directly out to the indoor pool area. 

The Catskills: A Place Worth Getting To Know

As you can see, from quaint villages to ritzy casinos, Woodstock Music Festival roots to farm-to-fork cuisine, there are amazing things to do in the Catskills of New York. All of the places you see pictured here are on the 70-mile stretch of the Upper Delaware Scenic Byway and just waiting for you to pay them a visit. 

I hope you enjoyed some of my suggestions. If given the opportunity, I would encourage you to explore this beautiful region of New York for yourself. Drive safe!

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

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Check out more of our area 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.