17+ Art-Centric Things To Do In Catskill NY on a Couples Retreat

Though a part of the Great Northern Catskills, Catskill, New York belongs, also, to the Hudson River Valley. Right on the Hudson River, this is where our forebears, including the eminent American painter, Thomas Cole, came to revel in the beauty of the Catskill Mountains.

You can tour Cole’s home and studio, wander an adorable Main Street peppered with painted cats, and dine on the bounty of the Hudson River Valley. Scroll down for our curated list of all the best things to do in Catskill NY.

Pair this getaway with a visit to the other small towns in the Catskills. Discover a new casino and a vegan retreat in the Borscht Belt town of Monticello NY and Catskill Utopia in Mountain Dale NY. In Bethel NY, site of the infamous Woodstock Music Festival, visit a museum paying tribute to the history-making event. Cross the river into Hudson NY, to visit Olana, home of the other Hudson River School of Art great, Frederick Church. And explore that artsy downtown as well. 

Looking for more weekend getaway ideas? Check out our roundup of romantic getaways in New England.

Where Is Catskill NY?

Catskill is a charming town situated in Greene County, New York, along the western banks of the Hudson River. It’s approximately 110 miles north of New York City and about 40 miles south of Albany, making it an accessible escape for those coming from major metropolitan areas. Found on the eastern edge of the Catskill Mountains, the town serves as a gateway to the vast Catskill Park and is a magnet for outdoor enthusiasts, artists, and those seeking a quieter, scenic atmosphere.

Incorporating the Catskills towns of Tannersville, Haines Falls, Hunter, Prattsville, and Windham, and the notch in the mountains known as Kaaterskill Clove, you’ll find many days of pleasure in these hills. What doesn’t change now is the protection of green forests, even if not formally recognized like the Muir Woods in the West.

Romantic Things To Do in Catskill NY

CROSS: The Huson River Skywalk

The Hudson River Skywalk serves as a six-mile out-and-back pedestrian link between two seminal locations of the Hudson River School of Art: the Thomas Cole National Historic Site in Catskill and Frederic Church’s Olana State Historic Site in Hudson. This elevated walkway crosses the Rip Van Winkle Bridge, providing a stunning platform for panoramic views of the Hudson River and its surrounding beauty.

As you traverse this scenic connector, you’ll literally be walking in the footsteps of iconic artists Thomas Cole and Frederic Church, whose landscapes were deeply influenced by these very vistas. It’s more than just a walk; it’s a journey through art history set against the backdrop of the river’s natural grandeur.

WALK: Historic Catskill Point

Yes, the town of Catskill is on the Hudson River – and where Catskill Creek merges with the greater river. Check out both recreational and commercial boat traffic, marinas, and sailboats at moorings. And be sure to take pictures of the Rip Van Winkle Bridge – it makes for a perfect selfie or friendie background.

TOUR: Thomas Cole National Historic Site – Catskill NY

Like the Catskills Region’s writers, Washington Irving (Legend of Sleepy Hollow, Rip Van Winkle) and James Fenimore Cooper (Leatherstocking Tales, Last of the Mohicans), Cole romanticized nature. He viewed it as an expression of the divine.

Cole lived here, often taking forays into the mountains to paint. Much of the landscape is just as he rendered it on canvas (though he worked from sketches and tended to enhance and transform them from “real” to “ideal”).

Born in England in 1801, Cole emigrated to the US with his family in 1818. He visited the Catskills in 1825, roaming the peaks and valleys of the Catskill Mountain range, sketching its splendor and selling his work to New Americans who were eager for art that captured the spirit of the countryside.

Cole married Maria Bartow, whose uncle owned Cedar Grove, this Federal Style Catskill homestead. He subsequently moved in with Maria and her three sisters (all wards of “Uncle Sandy) here.

You’ll begin your tour overlooking the Catskills in the distance and the same tree that stood here in Cole’s day near the front door. Your guide reads excerpts from Cole’s letters and diaries: lyrical, poetic entries on his life and surroundings.  

Take a gander at the artist’s paint box, his writing desk and his old studio – rustic in “unplastered brick” just as he described it.  

Find this, Frederick Church’s Olana, and several of the hiking trails listed below on the Hudson River School Art Trail.

HIKE: The Catskill Mountains

Kaaterskill Falls Trail

This 2.6-mile out-and-back trail leads you to one of New York’s highest waterfalls, made famous by a Thomas Cole Painting. The scenery is striking, and it’s a popular choice for couples looking to capture some great photos together. Note – DO NOT ATTEMPT TO PARK ON NY Route 23A; the only parking available is at Laurel House Trailhead, and it can fill up quickly on weekends.

North-South Lake Loop – Famous For The Fried Chicken War

This easier, 4.2-mile loop offers a flat terrain and beautiful vistas of the lake, mountains, and foliage. Look for signs of the remains of the Catskill Mountain House and Kaaterskill Hotel – at 1,200 rooms, once the largest mountain hotel in the country.

Local lore has it that Philadelphia businessman, George Harding, stepped into the 400-room Catskill Mountain House and demanded fried chicken for his daughter, who could not eat red meat.

As The Catskill Mountain House was serving only Roast Beef that evening, the owner bellowed – “If you want fried chicken, you’ll have to build your own hotel.” Harding took the challenge – opening the bigger and better Kaaterskill Hotel right at the top of Kaaterskill Falls, less than a mile away.

The feud, known as “The Fried Chicken War,” was forever stamped in Catskills history.

Indian Head Mountain Loop

A 5.6-mile loop trail that offers a more challenging hike featuring a summit with breathtaking panoramic views. Ideal for couples who are experienced hikers and enjoy a good physical challenge.

Platte Clove Preserve

Spanning 2 miles, this trail takes you through a ravine and to a series of waterfalls. With the enchanting sounds of cascading water, it’s an ideal setting for romance.

Pratt Rock

Put your sturdy boots on for the 500-foot climb up the crumbly steps of what has been termed a “monument to vanity.”   Zadock Pratt, tannery tycoon and Congressman, born in 1790, hired an out-of-work stonemason to sculpt his life story in the soaring cliffs near his house.  The result is as offbeat an attraction as they come, with views of the surrounding area worth the ascent.

Afterward, drive a few miles into Prattsville to the Pratt Museum in Zadock’s home for more information about the man.

Windham High Peak

A 7.4-mile out-and-back trail offering stunning vistas and a challenging climb. The summit makes a perfect backdrop for a romantic lunch, overlooking the Hudson Valley and the Catskill Mountains.

WALK: RamsHorn-Livingston Sanctuary

On the far side of the creek, you’ll find this oasis for birds and other shoreline wildlife. Take a two-mile walk through forest, ponds, and wetlands –  a nice feathered-friend diversion after all of those cats.

SKI/HIKE/BIKE: Hunter Mountain

Hunter Mountain, located in the Northern Catskills of New York State, stands as a year-round destination for outdoor enthusiasts. Known primarily for its winter sports, the resort offers a range of skiing and snowboarding options across its 320 acres of skiable terrain.

In the warmer months, the mountain transforms into a haven for hiking, and mountain biking. The 4,040-foot summit provides breathtaking panoramic views of the surrounding Catskill Mountains and Hudson Valley.

SKI/MOUNTAIN BIKE: Windham Mountain

Ski in the winter, bomb down the mountain on two wheels come summer. Windham is building up its reputation as a mountain-biking mecca. The Huckleberry Trail, which begins in Tannersville, has been expanded from an easy 2.2 miles into more difficult portions of the mountainside.

VISIT: Foreland – Catskill NY

Housed in a meticulously restored 19th-century mill, Foreland is a creative hub that features art galleries, artist studios, and artisan shops. Walking through Foreland feels like exploring an ever-changing canvas where local and national artists display their work.

The site often hosts workshops, art openings, and other events that make it a dynamic part of Catskill’s cultural scene. It’s a spot where creativity and history intersect, offering visitors a chance to soak up the artistic atmosphere while enjoying the mill’s architectural charm.

VISIT: Greene County Council of the Arts Gallery – Catskill NY

See what artistic locals are up to in this great little art gallery. From paintings to ceramics, and um, colorfully designed pistachio shells, it’s got something for everyone. Even if you just want to browse.

But you just might want to help an emerging artist by picking up a painting or work of art at a fraction of what you’d pay for a piece from an established artist.

SHOP: Main Street – Catskill NY

It’s that typical art-commerce-regular humble downtown where the small police station is next door to a pizza slice place, which stands next to the firehouse, and on and on. But in recent years, more and more shops are popping up, offering an eclectic range of wares on Main Street.

Head to Stinging Nettle Apothecary for herbal remedies, custom tea blends, and handcrafted products that celebrate the healing power of plants.

Stop into L&M Studio to watch artisans crafting porcelain tableware or into Catskill Chocolate Co., to see artisanal chocolates being crafted with love.

Pick up a great book at indie Magpie Bookshop or everything you want but nothing you’d ever buy for yourself at Mahalo Gift Shop.

SEE: The Catskill Cats

They might not be “clean as country water, or wild as mountain dew.” But these painted, decorated, dressed-up plastic kitties are all the rage every year. People make a fe-line to Catskill just to see them. 

VISIT: Catskill Fly Fishing Center & Museum – Livingston Manor NY

Nearby Roscoe, NY was “Trout Town USA.” In fact, fly-fishing actually begat tourism in the Catskills. So it makes sense to stop into this informative museum, set on 53 riverfront acres, dedicated to preserving the fly-fishing heritage.

In addition, you can fish in the Willowemoc Creek, picnic in a family pavilion, and practice casting. The museum itself features lots of glass cases, walls, and corners filled with everything to do with the Angler lifestyle. Peruse delicate hand-made flies, photos of famous fly-tiers, tourism posters, and a unique Casting Simulator Machine.

The Fly Fishing Center is a fascinating institution, and not just for seasoned fly fishers. Located amidst lush landscapes, the museum showcases the rich history of fly fishing, complete with vintage fishing gear, educational displays, and interactive exhibits. They also host fly fishing workshops and events throughout the year.

Catskill NY Restaurants

EAT: Willa’s Bakery Cafe

Located in the same industrial structure as Foreland, Willa’s is a must-visit spot for foodies exploring Catskill, NY. We love it for a casual, yet hearty, weekend brunch, but they also serve lunch. This is where to meet locals and artists based next door.

EAT/LOWBROW: A&G Texas Weiners

It’s an old-fashioned fountain shop with counter service, round stools, and dogs sizzling on the grill. In other words, awesome. Try the Texas Dog with chili or the Italian Hot Dog with onions, peppers, and potatoes. Splash on some of Nick’s homemade hot sauce (you can buy some to take home) for an extra kick.

EAT: Village Pizza II

Many say you won’t find a better pie outside of NYC. 

EAT/VIEW: Frank Guido’s Port of Call

The food is decent, but the views are outstanding at this creekside spot. Come for a glass of wine and a couple of appetizers, and you’re all set. The pours, thank you very much, are generous, providing you with ample time to watch the sunset over the docks.

EAT: New York Restaurant

New York Restaurant offers a blend of old-world charm and modern culinary flair. Housed in a historic building, the establishment is known for its Eastern European-inspired dishes as well as American classics. It’s an ideal place for couples looking for a unique dining experience, complete with wine pairings and artisanal cocktails.

DRINK/EAT: Rip Van Winkle Brewing Company

Joey LaBianco is the master brewer, while his Mom, Angela, cooks the food at this casual Italian eatery. Come for homemade pasta – and wash it down with award-winning house-made beer. 

Catskill NY Hotels

STAY: The Kaaterskill Inn – Catskill NY

A few miles out of town, this rustic-luxe property is winning raves from guests with posh rooms that Mother Nature herself would adore.

STAY: Rosehaven Inn – Haines Falls

Situated at the head of the magnificent Kaaterskill Clove, high in the hills above Route 23, this restorative, four room Arts and Crafts B&B is literally a breath of fresh air. Owned by the ebullient Kelly Coughlin, Rosehaven is a true haven.

Guestrooms are beautiful and immaculate, with high-end bedding you don’t want to leave. In the common areas, whatever is not polished wood – floors, wainscoting, some overhead surfaces – is covered with fancy wallpaper. In fact, the wallpaper not only lines walls but adorns ceilings as well (a signature Coughlin embellishment).

Take breakfast in a stately dining room or on the home’s inviting wraparound porch with fantastic Catskill Mountain views. The fare, especially Kelly’s Cheesecake Scones, vies with the vista for excellence.

STAY: Fairlawn Inn – Hunter

Just past the entrance to Hunter Mountain on Route 23, this beautiful nine room B&B was once the 1904 summer home of prominent Jewish philanthropist, Harry Fischel. Fischel helped establish a kosher kitchen on Ellis Island and was benefactor of many Jewish institutions including Yeshiva University.

Updated with an inviting patio, fantastic architectural features, and a wild, don’t-know-where-to-look-next fantasia of Victoriana (including Tiffany Lamp reproductions), the Fairlawn is a terrific “offbeat” yet upscale place to bed down.

More Weekend Getaways In Catskill Towns

• Woodstock NY
• Bethel NY
• Monticello NY
• Mountain Dale NY

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