The Most Unique Things to do in the Catskills

colorful town of Tannersville near Hunter in the Catskills in Upstate New York

Looking for the most unique things to do in the Catskills? This popular Upstate New York getaway is full of all kinds of one-of-a-kind experiences and unique Catskills attractions worth checking out on a getaway!

One of the best on the East Coast is a Catskills winter getaway located just outside of New York City making it an easy escape for city dwellers like us but boasts enough wonderful things to do in the Catskills that makes it a popular getaway in the NorthEast any season.

This scenic mountain region in New York has attracted and inspired artists and creatives and is an all-season mountain getaway for adventures, explorers, and anyone needing a dose of nature and the great outdoors from the city.

Check out our favorite picks for things to do in the Catskills, NY!

Interesting Things to do in the Catskills

Karma Triyana Dharmachakra Monastery

Karma Triyana Dharmachakra Monastery in Woodstock New York in the Catskills

Located in Woodstock in the Catskill Mountains, the Karma Triyama Dharmachakra Monastery is a popular site for those connecting to their spirituality.

One of the unique things to do in the Catskills, NY is to pay a visit to this Tibetan Buddhist monastery. This location is the monastic seat of His Holiness the 17th Gyalwang Karmapa, Ogyen Trinley Dorje in North America.

This location features a Shrine Building and a Monastery Building. The Monastery Building provides accommodation for guests and staff of the monastery.

This monastery also houses a huge library filled with books about the Tibetan religion, travel, art, philosophy, and practice. There is a facility where Tibetan music can be recorded along with a large gallery featuring Tibetan paintings and statues.

If you would love to visit this unique Catskill location, feel free to join any of the two tours held each week. There are several programs held here round the year and they are always open to visitors who might be interested in learning about the Tibetan religion and Buddha’s teachings on compassion and wisdom.

Be sure to explore all the best things to do in Woodstock while you’re here too! We highly recommend planning a meal at one of their many great places to eat while you’re in the area.

Opus 40

Built by Harvey Fite, this grand site is a masterpiece crafted on an abandoned bluestone quarry. Fite intended to use this location as a showcase for his sculptures and estimated that the site would be completed within 40 years.

Built by hand alone without cement or mortar, Opus 40 features hundreds of thousands of stones artistically put together to form a series of terraces, steps, and ramps that cover over 6.5 acres of land.

Opus 40 also features a 9-ton monolith and has several pools and fountains which are fed by springs in the quarry. When looking for unique things to do in the Catskills, take a trip to Opus 40 and walk through the cool subterranean passageways and get lost in this one-of-a-kind sculpture garden and park.

Located in Saugerties, Opus 40 also features a Quarryman’s Museum. Here, you can find authentic 19th-century quarryman’s tools and furnishings. This location has become a hotspot for tourists, weddings, picnics, and other outdoor events.

Wallkill Valley Rail Trail


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Top on the unique Catskills attractions is this 22+ mile trail on a former railway. It runs through the former Wallkill Valley Railroad rail corridor in Ulster County all the way to Gardiner, New Paltz, Rosendale, and the Kingston city line. This location is great for jogging, walking, horseback riding, bike riding, cross-country skiing, and hiking.

This trail features an unpaved stone surface. Hikers get to pass through Rondout Creek, Wallkill River, Rosendale Trestle, and Shawangunk Ridge. The trail is open all year round from dawn to dusk. Be ready to enjoy beautiful sightings of unique birds and other animals along this trail.

One fun fact about this location is that the Wallkill Rail Trail Bridge was one of the filming locations for the Oscar nominated sci-fi horror film ‘A Quiet Place” starring John Krasinski and Emily Blunt.

Fabulous Furniture

Fabulous Furniture roadside stop a unique Catskills attraction in New York

One of the most unique Catskills attractions is this wacky roadside furniture store. Located in Boiceville, Fabulous Furniture features special furniture made from trees.

The wood used to make this furniture is left undyed and they retain the tree’s natural beauty. This unique Catskills roadside attraction also has huge sculptures that look like UFOs and robots. These are made from metal and car parts.

Created by Steve Heller, this authentic furniture store has the best-handcrafted tables and mirrors in the Catskills. Heller has been creating unusual wood and metal sculptures like robots, dinosaurs, cars, and many other things borne from his love for sci-fi craft.

You really can’t miss this when you drive past it, the wacky sculptures are what made us stop and take a peek!

Be sure to add this unique furniture shop in the Catskills to one of the things to do in the Catskills and enjoy the skill and craftsmanship that goes into creating these interesting pieces.

Overlook Mountain Ruins

Located near Woodstock, Overlook Mountain House Ruins is one of the first and oldest luxury hotels in New York State. It was built by James Booth as a vacation resort in 1833.

During the Civil War, the Overlook Mountain House was the top first-class resort hotel in the US. This grand architectural masterpiece was destroyed by fire in 1875 and was rebuilt in 1878.

In its heydey, it could accommodate up to 300 guests. It was razed by fire a second time in 1923 and was partially rebuilt in concrete.

Since its reconstruction was never completed, this location has become one of the most visited unique Catskills attractions as it sits in ruins and nature is reclaiming the land around it. Hikers pass through the Overlook Mountain Ruins as several trails run through its location on Overlook Mountain just outside of Woodstock.

Dundas Castle Ruins

Dundas Castle in Roscoe New York in the Catskills

Dundas Castle Ruins is a unique Catskills attraction and one of the coolest castles in New York, yep New York has castles! Also known as Craig-E-Clair castle, this was originally built by Ralph Wurts-Dundas, this cool architectural gem in the Catskills is modeled after a medieval Scottish Castle and surrounded by a magical atmosphere.

Dundas Castle is enigmatic and no one really knows the entire history of this site other than the land was purchased and construction started by Wurts-Dundas in 1915. He passed away in 1921 as the castle approached completion.

Dundas’s wife was committed to a sanatorium soon after his death, and the castle’s possession and management changed several times with an abundance of drama and mystery. No member of the Dundas family ever resided in the castle itself!

The castle is on private property, so you need to arrange a visit beforehand to witness this abandoned, decaying castle hidden in the hills in Roscoe near the Pennsylvania border and has been added to the National Register of Historic Places. 

Hunt Covered Bridges

Perrines Covered Bridge in New York

If you are looking to spend some time in the region or driving around Upstate, one of the fun things to do in the Catskills is taking a tour of the historic covered bridges in the area.

There are about 20 historic covered bridges in New York located in several charming villages and Upstate towns. Many of these bridges date back to the early 1800s and some of them still accommodate motor traffic to date or you can just park and walk across by foot.

Some of the beautiful historic covered bridges in the area making it one of the most unique things to do in the Catskills include: Halls Mills Covered Bridge, Livingstone Manor Covered Bridge, Beaverkill Covered Bridge, Bendo Covered Bridge, Chestnut Creek Covered Bridge, Perrine’s Covered Bridge, and Ashokan Covered Bridge.

Check out the best towns in the Catskills to visit, many of which have covered bridges nearby!

Rip Van Winkle Trail & Monument


Have you ever heard of the story of Rip Van Winkle? This short story by author Washington Irving published in 1819 about a man who takes a long nap in the Catskill Mountains. My favorite and most memorable rendition of this story was by the beloved dog Wishbone, an old PBS show from my childhood, haha.

Anyway, Washington Irving actually had his home, Sunnyside in Tarrytown, near Sleepy Hollow where he also wrote the Legend of Sleepy Hollow, the classic tale about the Headless Horseman and Ichabod Crane, so writing about these place in Upstate New York was no stranger to Irving using them as the setup for many of his most celebrated work.

One of the most unique things in the Catskills you can do is trace the Rip Van Winkle trail and monuments dedicated to this famed story!

The Rip Van Winkle Monument is located on Hunter Mountain. It is a larger-than-life depiction of Rip Van Winkle who was a famous literary character in Washington Irving’s book. Made out of bluestone, this monument is a unique location in the Catskills for picnics and hikes.

Take a sky ride from Hunter Mountain to get to this unique Catskills monument. You can also enjoy sweeping views of the Catskills Mountains from the location of the monument.

Tourists who are looking for things to do in the Catskills can take a hike on the Rip Van Winkle Trail. There are guided tours available for this trail if you want a guide to provide all the info for you!

Hikers will enjoy exploring the legendary cloves where Rip took his long nap. You will also enjoy seeing colorful statues set around the mountain top region. A gurgling stream, refreshing spring, and a raised garden site are all part of the attractions found on this trail.

And while you’re here, you’ll probably notice a lot of other Rip Van Winkle-themed things, I personally loved the Rip Van Winkle mural on the side of the big antique shop called Tannersville Antiques in Tannersville – another pick for one of the most unique things to do in the Catskills!

Go Back in Time in Tannersville 


Known as the painted village in the sky, Tannersville is located in the heart of the mountains around Hunter. Filled with adventure and fun activities all year round, this is one of the unique places to visit in the Catskills.

Visit Tannersville during winter and enjoy skiing, tubing, riding, and other great outdoor winter activities at nearby Hunter Mountain, one of the best Catskills in winter attractions.

Tannersville is also especially known for its colorful 19th-century storefronts and charming antique shops. It honestly feels like a really colorful western town!

This is a great option for stopping for lunch, especially if you’re enjoying other nearby attractions including Kaaterskill Falls. Or stop by just for the amazing antique shopping, there are several antique stores in this small, colorful western town, or visit the old-fashioned shop and eatery at The Catskill Mountain Country Store & Restaurant.

Kaaterskill Falls


Frozen Kaaterskill Falls in winter

Love waterfalls? How about visiting one of the most beautiful waterfalls in New York? One of the most unique things to d  in the Catskills is visit Kaaterskill Falls whether you plan on doing the full hike to the base or just want to head to the upper viewing platform for a quick glance at this natural stunner!

The stunning Catskills landscape has made it quite popular with tourists and inspired artists, photographers, and other creatives for ages.

Kaaterskill Falls is the highest cascading waterfall in New York State. It has two tiers and drops over 260 feet. 

For a quick visit, head to Laurel House Trail Road and park up here to walk to the overlook and viewing platform from the top of the falls. This is great any time of year as we visited in the winter and with snow boots the trail was easy to traverse.

You can also do the longer 1.4-mile hike from the base of the falls which also passes Bastion Falls, an additional waterfall. The trail through Kaaterskill Falls is the most popular trail and unique Catskills attractions especially when it comes to natural beauty.

When hiking through this trail, you need to be very careful as the trail can be muddy and filled with slick stones which is fine as long as you wear proper hiking footwear. If you plan to get to Kaaterskill Falls, ensure that you park only at the designated areas to avoid getting a ticket and if you’re in the summer – check for ticks afterwards!

Scott’s Family Resort


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Planning a vacation in the Catskills? You should check out this family-owned lakeside resort. This resort was the filming location of “The Marvelous Mrs. Maisel,” the popular tv show that you’ve most likely heard about, if not get on Amazon Prime and watch it!

It’s no secret we are fans and we even visited other filming locations in NYC including in Nolita!

Scott’s Family Resort is featured in season 2 when Midge’s family goes on their annual summer retreat in the Catskills. The relaxed, quiet location is loved by guests and visitors looking to enjoy the quiet beauty of the Catskills.

Scott’s Family Resort has been open to guests for the past 150 years and it features a series of rooms, cabins, and a cozy, comfortable inn located on Oquagua Lake. The property was recently for sale and repurchased, so hopefully, things don’t change too much!

The resort itself has a bowling arena, volleyball and basketball courts, a 9-hole pitch and putt course, 3 ping pong tables, a couple of pool tables, chess sets, and an ice cream bar. So if you get a chance to visit or stay here, do it – especially if you’re a Maisel fan, this is one of the best unique Catskills attractions for you!

Zip Line

Adrenaline lovers, you’re going to love this unique Catskills attraction! A Catskills getaway cannot be complete without a zip line tour through the scenic landscape if you’re looking for an exhilarating rush!

Head on to Hunter Mountain and join the New York Zip Line Adventure Tour. This is the fastest, highest and longest zip line canopy tour in all of North America. If that’s not impressive enough, it’s also the 2nnd largest zip line in the world!

This zipline course offers 6 separate zip lines, four rope bridges, one rappel, and nine aerial tree platforms. Try the SkyRider Tour which is the one that holds the title for the 2nd longest zipline in the world at 600 feet above ground, speeds up to 50mph, and lasts 3 hours!

Visit the Site of Woodstock Music Festival

One of the most unique things to do in the Catskills is visit the site of the most famous music festival in history, the site of the 1969 Woodstock Music Festival. What most people don’t realize is that Woodstock wasn’t actually located in Woodstock, another popular Catskills town that is still alive with the hippy and 60s culture of peace and love.

This historic site is actually located in the town of Bethel; about 40 miles southwest of Woodstock.

It commemorates the 3-day music festival which occurred from August 15 to 18, 1969. The 300 acres of farmland can be found in Sullivan County, New York. About 450,000 people gathered on this site to experience and expression of cultural, musical, and political realism that transformed the American culture and became a symbol of faith and the fellowship of a generation.

The 3-day festival featured several thrilling and eye-opening performances from 32 folk singers, rock and roll bands, and blues performers.

One of the most influential performers was Richie Havens. He opened the concert and did an impromptu improvisation of the song ‘Freedom’. This became of the top highlights of the festival. Other performers include the Grateful Dead, Crosby, Country Joe McDonald, Nash, Joan Baez, and the amazing Jimi Hendrix to name a few.

Today, the site of the Woodstock Music Festival holds a museum and historic tour of the site. Visitors can buy tie-dye gifts, vinyl, and the peace, love festival gift items.

A Night at the Roxbury


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Another one of the most unique things to do in the Catskills, NY is enjoy an immersive experience out of this world at this crazy-themed hotel. 

The Roxbury Hotel is every movie lover’s dream or anyone looking for a unique Catskills experience. Nestled in the heart of the picturesque Catskill Mountains, each of its rooms is themed and feels like living in a movie or TV show from the 60s, 7os, and 80s.

There are two properties that makeup the Roxbury Experience, the Roxbury Motel and The Roxbury at Stratton Falls. The two properties are located one town apart from each other, about 2 miles or a 3 minute drive.

The most famous property are the unique rooms at the Roxbury Motel. If you love Gilligan’s Island, you will love the room named “Maryann’s Coconut Cream Pie”. This room features a ceiling designed to look like whipped cream. It also has some pie crust crown molding and a pretty pie circular bed.

Love the Wizard of Oz? There’s a room at the Roxbury for you complete with a yellow brick roadbed and a wall size painting of the Emerald City.

Sci-fi geeks will love the ‘Final Frontier” room which takes you into a realm of a new civilization. This room is decorated like a spaceship and features a moving 20-foot ceiling which has a fiber optic shooting starlight show. If you are a Star Trek fan, this is the room for you!

At the Roxbury at Stratton Falls, you can choose between the quirky Tower Cottages and gorgeously themed Mansion Rooms plus enjoy the glistening cascades at Stratton Falls.

This hotel offers easy access to Catskills Park along with the forest preserve, exhilarating hiking trails, a spa at both locations, and a pool at the Stratton Falls location.

Cell service in this location is not so great so this is a perfect location for you to unplug and enjoy the wonders of the Roxbury Hotel and the wonders of the beautiful Catskills Park.

Visit the World’s Largest Kaleidoscope

The Worlds largest Kaleidescope at Emerson Resort in Phoenicia New York Catskill Mountains

One of the most obvious choices for unique things to do in the Catskills is visit the World’s Largest Kaleidoscope at Emerson Lodge in Phoenicia, New York.

This kaleidoscope is housed in a silo and towers at 60 feet tall and 37.5 feet wide. Recorded in 1997 by Guinness Book of World Records, this huge kaleidoscope was designed by Charles Karadimos.

Kaleidoshows are held here on a regular basis and a must! This was actually one of our favorite things to do in the Catskills while exploring Phoenecia and the surrounding area. The original shows were designed by Isaac Abrams and his son, Raphael.

In 2016, a new show was created. It features an immersive visual and audio experience and was created by Shea Johnson, Alicia Ramirez, and Austin Johnson.

This show is suitable for people of all ages and can be viewed from the bottom up. It is best to lie on the floor or lean on the wall while viewing the show. The shows last for about 15 minutes and costs only $5 for non-guests of the Emerson Resort. If you’re staying at Emerson, the kaliedioshow is free!

Apart from enjoying the kaleidoshow, visitors also get to learn about the history of kaleidoscopes and the story of the brilliant artists that created them. Step into the Emerson stores where you will find several scopes made of brass, veneer wood, turned wood, glass, chrome, and marble. Most of the scopes you will find in the store are one of a kind and are signed by their artists, making it one of the most unique Catskills attractions money can buy!

Where to Stay: Catskills, NY

Walden Lodge at Urban Cowboy Catskills in winter in New York

Exploring all the unique things to do in the Catskills can take days, which is why we recommend spending at least a weekend if not a few extra nights to explore all the fun and unique Catskills attractions.

With several amazing options available for you to pick from, it can be daunting to pick, that’s why we have an entire guide for where to stay in the Catskills for more options.

Here are a few of our top picks!

The Roxbury Hotel: As already mentioned earlier in this guide to unique Catskills attractions, The Roxbury Hotel is an obvious choice and one of the most one-of-a-kind things to do in the Catskills on its own with their themed properties in amazing locations that make exploring the area easy.

Urban Cowboy: This lodge is where we stayed and makes for the perfect base to spend during your Catskills getaway. This former Bavarian lodge was owned by the same family for nearly 70 years before retirement, they sold the lodge and its five standalone buildings to the creatives who brought a luxury, curated, wilderness lodge experience.

Each room has something special to offer and is individually designed and is what aesthetic dreams are made of not to mention the clawfoot bathtubs next to a fireplace next to the giant windows overlooking the mountains, which is just stunnnig any season. Urban Cowboy Catskills is a place to unplug and unwind, rooms have no televisions, instead, bring a little speaker, turn on some tunes and soak in the tub with the view or play one of the board games they lend out.

Mohonk Mountain Resort: Located in Hudson Valley, this grand resort is surrounded by 40,000 acres of pristine forest and features a luxurious spa, continental farm-to-table dishes, and tastefully decorated historic rooms, suites, and lodges all set in a Victorian castle and one of the most famous mountain resorts in the region. Mohonk Mountain Resort is also a National Historic Landmark.

Emerson Resort & Spa: Featuring spacious accommodations with huge windows and tasteful Victorian decorations, this resort is one of the best places to stay while exploring the best things to do in the Catskills. Emerson Resort & Spa is one of the most popular and well-known luxury properties located in Phoenicia plus this is where you can see the world’s largest kaleidoscope.

The Graham & Co.: Another one of the most popular places to stay in Phoenicia is this beautiful, chic boutique motel located in the heart of the village and perfect for exploring the best things to do in the Catskills. The location is already amazing but this experience is an elevated one while still somehow remaining unpretentious.

The Graham & Co.sits on 3 acres of property which offers 2o rooms, a swimming pool, hammocks to lazy in during the warmer months, a badminton court, fire pits, picnic spots, and bikes you can borrow if you’re a guest. 

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