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Mention that you’re planning a road trip through New York’s Catskills and questions always follow. Isn’t that where the movie Dirty Dancing was set, and HBO’s Marvelous Mrs. Maisel vacationed with her family? Are you going to the Woodstock anniversary?

While the Catskills remain as alluring as they are onscreen in real life, there’s much more to them than picturesque views and Woodstock history. Native Americans hunted the region for eons, following trails and foraging as they went. You can still trek from the Hudson Valley, following the Catskills all the way south to the Appalachian range, but the route is much easier by car or train, especially on a trip with multigenerational companions.

The Catskills are beautiful whatever season you go. Roads wind through verdant hills in the warmer months, forests are resplendent with ruddy colors in the fall, and winter brings picturesque blankets of snow. There are multitudes of roadside attractions and unique villages, historical sites, and estates open to visitors year round.

Spice up your multigenerational road trip with these stops through the region.

Owego's Parkview Restaurant and Pub in upstate New York.

Owego And The Haunted History Trail

The village of Owego is full of friendly locals who love to share their stories about hauntings. The Parkview Inn, which was abandoned for years, stands near the river and has just been renovated. The construction has revealed secrets and apparently disturbed several deceased guests who departed in an untimely manner.

During the Halloween season, the annual Owego Zombie Fest roars to life with parties and costume contests, but you can investigate the hotel as part of New York State’s Haunted History Trail year round. Try communing with guests who died or were involved in murders in the building. You may even hear a dinner bell ringing. That’s two-year-old Marguerite who rocked her chair too close to the fireplace and perished in 1909.

The daily coffee klatch at the bar may be attended by three ghostly cowboys accused of killing a man in the basement where his bones were discovered. While 2012 renovators were putting in new plumbing, a sealed-off room was found. The “Crying Room” was named by a paranormal expert who claimed that a child died there.

Not smitten with Owego’s otherworldly offerings? All is easy along Main Street, with its shops, galleries, tempting bakeries, and cafes, ensuring something for everyone at this Catskill road trip stop.

The Philipsburg Manor in Sleepy Hollow.

Ghosts, Headless And Chained

If someone in your group needs more ghouls, Sleepy Hollow is another must-visit Catskill stop for you. Washington Irving envisioned the chilling characters in his stories of the Headless Horseman and Rip Van Winkle at his Sleepy Hollow estate, Sunnyside. Each Halloween, ghostly visitors and spooktacular events happen throughout Sleepy Hollow from Sunnyside to the opulent Van Cortlandt Manor, built right after the American Revolution.

During the holiday season, nearby Philipsburg Manor hosts a Holiday Boutique. Encounter Ebenezer Scrooge and his ghostly visitors during productions of Charles Dickens’s A Christmas Carol in the Old Dutch Church across the lane from Philipsburg Manor.

A photo from inside the Woodstock Museum.

The Original Woodstock

Don’t miss the Bethel Woods Center for the Arts, the concert center and collection of galleries built to memorialize the original Woodstock Festival. The stone building houses several galleries and a fascinating museum, and sits adjacent to the concert grounds where the 1960s rock-and-roll experience changed the world.

Celebrate Woodstock’s 50th anniversary with parties and concerts through 2020. Whether or not you’re a fan of music and American history, you won’t regret taking the family through the best Woodstock museum on the planet. Cross the grounds to overlook the field where the Summer of Love began. You might meet members of the original Woodstock generation who still hang out there and are happy to share their recollections.

The Resorts World casino and spa in the Catskills.

Jefferson Slept Near

The seat of Sullivan County, the town of Monticello, is named after President Thomas Jefferson’s Virginia estate. Outside of town, the palatial Resorts World casino and spa rises above the treetops. While Resorts World caters to anyone looking to get their game on, families are welcome. The indoor pools provide space for children as well as adult-only waters.

The Yo1 Wellness Center, also in Monticello, opened in 2018 on 1,300 acres of forest. The lakeside center offers Ayurvedic treatments and diet plans in a sleek, new setting. Relaxing Crystal Life Signature Rituals include massages and facials.

Home of the World's Largest Kaledioscope.

Big Sights And The Largest Kaleidoscope

Mount Tremper's Emerson Resort & Spa hosts the World's Largest Kaleidoscope and the adjoining gift shop runs a kaleidoscope-inspired film by Heady Productions daily. Recline and allow the music and twisting colors, shapes, and reflections to transport you and all your travel companions. Children under 12 are admitted to the show for free. Older guests pay $5 per person. The shop is full of hundreds of kaleidoscopes from small to giant; some include precious stones as well as cut glass.

The Byrdcliffe Theater in Woodstock Village.

Woodstock, The Village

It’s easy to be confused, but this is not where the 1969 Woodstock Festival took place. Woodstock Village reneged on its promise to host the original festival after tickets and the iconic poster were printed, but the concert organizers went ahead with the name. Luckily, Max Yasgur offered acres of his dairy farm in Bethel Woods for the concert, never expecting it to be so large. His neighbors in surrounding villages protested to no avail and the rest is history. Today, the town where Woodstock would’ve been hosted has embraced its adopted legacy. A vibrant arts scene flourishes here, and the 1960s hippie vibe carries on in shops and galleries.

Park near the Byrdcliffe Theater and grab a one-hour self-guided walking tour map inside the Byrdcliffe Arts Colony gallery. There are 30 different Arts and Crafts style buildings on the route. A few highlights include the Eastover House built in 1904-05 to house the Byrdcliffe Art School faculty. Since then it's been a home and studio for The Band, Chevy Chase, and Sally and Milton Avery. Follow the stream that runs past the ruins of a little playhouse near the Fleur de Lis caretaker's house. When it’s hot out and after plentiful rain, the whole family can cool off in the Old Swimming Hole near the Barns Building.

The Thomas Cole National Historic Site.
Elaine Masters

Arts And Parks

The Thomas Cole National Historic Site is a quiet spot where you can stand on the veranda and glance across the river, which is still verdant and lush. Connect with the conservation spirit that drove British immigrant and painter Thomas Cole to founding the Hudson River School of Art, the first major art movement in the country.

In spring and summer, the home’s heritage garden overflows with plants and vegetables popular during the colonial era. The New Studio on the historic estate is an invitational art space for contemporary creators next to the 1939 Old Art Studio that’s still set up as if Cole had just stepped away from his easel. Follow the Hudson River School of Art Trail, where you can witness many of the settings that inspired artists from the movement.

Entrance to the Beekman Arms Inn.

Rhinebeck Antiques And Historic Taverns

In the center of Rhinebeck Village, Beekman Arms and Delamater Inn is America's oldest continuously operated inn and one of the Historical Hotels of America. Built in 1766, the rooms feature luxurious linens and colonial-style decor updated for comfort. The Antique Market behind the main building is packed with high-end pieces from many different vendors.

Nearby, the Dutchess County Fairgrounds stays busy year-round with classic car and antique shows, plus sheep and wool and wine and food festivals. Walk the town to window shop, sample teas, and dine at noted restaurants like Terrapin, known for its fresh take on local ingredients, or Foster’s Coach House Tavern, which has been operating in the same location for over 125 years.

If you’re looking to do something more active, get out on the Hudson River. Charter a sailboat through Tivoli Sailing or join a sunset or sightseeing cruise with Hudson River Cruises.

FDR and Eleanor Roosevelt's garden gravesites.

FDR Sleeps Here

Hyde Park is the setting of the nation’s first Presidential Library and the birthplace of Franklin D. Roosevelt, America’s 32nd President. The spacious estate also features his and Eleanor Roosevelt’s garden gravesites. Tours via mini-tram or trails will lead you from the visitors center into the family home, and to the Library and Museum. The Museum galleries are full of World War II posters and colorful displays that will appeal to children of all ages. The Vanderbilt Mansion and the Eleanor Roosevelt Historic Site are nearby.

Aerial view of Poughkeepsie from the Walkway Over the Hudson.

Walks And Wines Near Poughkeepsie

Poughkeepsie is a growing town less than two hours from Manhattan. Set alongside the Hudson River, it overflows with natural beauty as well as great restaurants and affordable lodging. The train station sits below the Walkway Over the Hudson -- currently the world's longest and tallest elevated pedestrian bridge. Stroll or bike the 3.6-mile Walkway Loop Trail for thrilling river views and cross over to the spur trail that will afford you access to Franny Reese State Park.

Poughkeepsie’s proximity to the Culinary Institute of America gives locals and visitors great dining choices as graduate chefs have opened restaurants and cafes throughout the downtown area. Consider lunch at The Artist's Palate and enjoy the culinary artistry on your plate as well as the rotating gallery of artwork.

East of Poughkeepsie, Millbrook Vineyards boasts sprawling acres of vines and nationally recognized wines available for sampling in Millbrook’s lavish tasting room. Family events include Millbrook’s Jazz at the Grille series, lobster bakes, and Friday food truck nights. The Vineyard Walking Trail winds along a hilly route to the top of the estate to expansive views of the Shawangunk and Catskill Mountain ranges.

The Culinary Institute of America.

Where Famous Chefs Are Created

The impressive Culinary Institute of America’s grounds rise from the Hudson River to a plateau in Hyde Park. Join a student-led tour of the immense building that was once a monastery. The halls are decorated with pictures, awards, and sculptures. There are large windows throughout -- all the better for observing future Top Chef winners honing their skills.

Four Culinary Institute restaurants are open to the public: American Bounty serves national favorites; classic French fare is available at The Bocuse Restaurant; authentic, regional Italian dishes are on the menu at Ristorante Caterina de'Medici; and casual dining is available in the Post Road Brew House. Reservations are highly recommended.

One Culinary Institute spot doesn’t need reservations. If your family still has room for dessert, take a seat in the Apple Pie Bakery Cafe or grab something for the road from the take out counter.

Chuang Yen Monastery in Carmel, New York.

Biggest Buddha

Before leaving the Catskills region, head to the town of Carmel and walk up the sculpture-lined entrance to marvel at the largest Buddha in the Western Hemisphere inside the great hall of the Chuang Yen Monastery. Renowned architect I.M. Pei consulted on the design and construction of the Hall of Ten Thousand Buddhas Encircling Buddha Vairocana. Visitors are welcome to respectfully walk around the giant Buddha to marvel at the 360 degrees of carvings and statues within. Look for towering statues of the goddess Quan Yin in the nearby temple and adorning the lake trail.

After working up an appetite at the monastery, stop by the river village of Cold Spring. The colorful village offers local brews, sandwiches, and much more. Walk the main street, where local artisans and farmers sell their wares. Then venture through the tunnel under the railroad tracks to admire Cold Spring’s riverside views. Cold Spring’s visitors can enjoy museums or take the trails that lace through the area. Beginner or advanced hikers have many trailheads around town to choose from.

The zipline at Hunter Mountain.
Elaine Masters

Choose From A Multitude Of Adventurous Excursions

The Catskills’ mountain-top towns are adventure central, with diversions to please everyone, year-round. The New York Zipline Adventure Company in Hunter runs the longest and fastest zipline in Northern America. In Haines Falls, Rip Van Winkle Snowmobiling and ATV keeps the intrepid racing -- with or without snow. Greenville is home to the World Championship-qualified Sunny Hill Viking Obstacle Course with hanging rope and wall climbs, log balancing, and more. Zoom Flume Water Park is a great place to splash down during warm summers in East Durham. Test your mettle on the 700-foot zipline over the park and gorge.

Closer to the Hudson River and the city of Catskill, Bailiwick Ranch and Animal Park will excite wildlife enthusiasts of all ages. The family residence, Bailiwick Castle, was built by Ashcan School artist Everett Shinn in the center of the property. While you’re in the area, admire views of the Hudson-Athens Lighthouse or climb aboard one of several charter tours in the area.

Whether your Catskills road trip companions are adults, toddlers, or teens, driving the hills and valleys will build memories for a lifetime.

Photo Credit: Murloc / Shutterstock

Photo Credit: Brandt Bolding / Shutterstock

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