The Roxbury Motel: Imaginations Unleashed in the Catskills

The beauty of walking into the Catskills’ Roxbury Motel is that whatever was weighing you down that day—money, parenting, traffic—vanishes instantly. Roadside lodging rarely offers jaw-dropping moments, but as soon as you slide that key into one of the lime-green doors and step into your assigned room you’ll have one, and be too enchanted to wallow in your daily stresses.

And it doesn’t matter which room you walk into: MaryAnn’s Coconut Cream Pie (room 27) or Miss Kitty’s Saloon (room 22) or maybe it’s Samantha’s Cloud (room 16), because each one has a theme that is meticulously designed by owners Greg Henderson and Joseph Massa, who hunt flea markets, estate sales, New York City design shows and the Internet for just the right bathroom tiles or one-of-a-kind lampshade. No detail is too small for their scrutinizing taste.

Each room is a thoughtful valentine, and the owners’ enthusiasm is infectious. When I stepped into “Amadeus’s Bride,” a sumptuous, turquoise and gold two-story suite decorated with 18^th century flair and anchored by a spiraled staircase, I prayed that this is how the afterlife will look.

To call the Roxbury Motel roadside lodging feels misleading despite its classic midcentury motel shape and location on County Highway 41 in Roxbury, New York, 150 miles north of Manhattan. Known officially as The Roxbury, Contemporary Catskill Lodging, this unapologetically funky, colorful oasis is surrounded by the beautiful blue Catskill Mountains and rolling farms, landscape that was once home to the so-called Borscht Belt, named for its popularity as a summer playground for New York City’s Jewish residents.

In the past decade, the Catskills have been experiencing a renaissance, with the opening of many new or renovated inns and resorts that strive to integrate quotidian pastoral tranquility. There’s often a self-serious vibe to such places. Reclaimed barn doors turned into dining room tables. Organic farm-to-table dining. Rustic cabins that lack TVs.

Forget all that.

In this quiet town of approximately 2,500 people where there is no grocery store, the Roxbury Motel has been making a name for itself since opening in 2004 with only 10 rooms.  Fast-forward to 2018, a few expansions later, and people from all over the world now come to stay and experience rooms that are tributes to the owners’ childhoods and favorite pop culture icons from the 1950s, 1960s, and 1970s.

Room 26, known as “Maria’s Curtains,” is an homage to the 1965 Best Picture The Sound of Music; the lamps are indeed “small paper packages tied up in string.” In Room 21, or “The Wizard’s Emeralds,” you can walk the yellow brick road. There are 28 rooms like this, including “The Digs,” a stand-alone, three-bedroom extravaganza with a 400-gallon saltwater fish tank. Oh, and I lost count of all the chandeliers and candelabras throughout the motel, including those in the spa and conference room (decorated in black, white and yellow). Lighting is mood, and Henderson and Massa take both very seriously.

My absolute favorite room is “MaryAnn’s Coconut Cream Pie,” a love letter to the television show Gilligan’s Island. It’s not that I was ever a fan of Gilligan’s Island, but that I became a fan of the owners’ fandom. I love that Henderson and Massa took their creativity to crazy theatrical heights; each room feels like walking onto a stage (both men worked the New York City theater scene), especially “Mary Ann’s Coconut Cream Pie.” The room includes autographed photos of actress Dawn Wells, who played Mary Ann, as well as tiki-style knickknacks, a faucet that echoes a captain’s whistle, and the pièce de résistance—a hand-sculpted ceiling of whipped cream dollops and pie crust with a meringue-like king-sized bed to match. I’ve slept on five continents, in cities, mountains, and on beaches, inside a yurt, a giant nest, and sky-high five-star luxury. Nothing parallels sleeping in a room shaped to look like a pie. You wake up under those faux dollops reborn; you can’t go back to chain hotels after something like that.

“We sell out pretty much every weekend of the year, especially during the summer, fall foliage and ski seasons,” said Henderson, who is often seen on Roxbury’s Instagram feed reporting the arduous undertaking of their current multimillion dollar expansion: the conversion of a historic mansion and the addition of eight cottages.

The mansion and surrounding property, which sits by scenic Stratton Falls, has reportedly only changed hands four times in nearly two centuries. In 2014, Henderson and Massa were approached by the current owner to purchase the property and bring their theatrical wizardry to it. Guest rooms inside the 1848 mansion will be a tribute to Roxbury’s history, such as “The Beautiful Blacksmith,” “The Ghost and Mrs. Hicks,” and “The Brothers Stratton.”  The eight cottages near the mansion will create a fairytale setting with themes such as “Vampire’s Fangs,” and “Cinderella’s Gown,” the latter inspired by one of Henderson’s favorite childhood books.

Finding the perfect detail is part of the fun for Massa and Henderson, who shared his find of a goose-and-gosling-shaped faucet for the future “Cinderella’s Gown” cottage in an Instagram video.

“We’re not a franchise,” Henderson said. “There’s nothing quite like us.  There are other themed hotels, but no one goes to the level of details that we do. Having 92 varieties of light bulbs makes no business sense, [but] we get so many repeat guests. People want to experience the different themes.”

I am soon to be a newly-minted repeat guest. I enjoyed my stay there so much in December, splitting my time between “Amadeus’s Bride” and “MaryAnn’s Coconut Cream Pie” that I’m returning this month to spend my entire birthday weekend back in room 27, ensconced in faux whipped cream. I’m not alone; the Roxbury has become a popular place for weddings, family vacations, romantic weekends, and girlfriend getaways.

The Roxbury includes a robust continental breakfast that goes beyond the standard stale muffin and coffee to feature a range of pastries, yogurt, fruit, meats, cheeses, cereals, jams, and six types of hot cocoa, plus always-filled candy dishes. Parking and Wi-Fi are free. Cell phone boosters are available since cell signals can get spotty in the Catskills. Rooms come equipped with small refrigerators, handy for storing restaurant leftovers (the Roxbury does not have a restaurant). There’s a small onsite spa featuring another one of the motel’s stunning chandeliers.

The new addition, known as The Roxbury at Stratton Falls, is scheduled to open in 2019, and will feature more spa amenities and an in-ground swimming pool. Skiing is available in all directions with Windham Mountain, Hunter Mountain and Belleayre Mountain and (with its new Catskill Thunder gondola) all about a half-hour drive away. The Roxbury posts ski condition updates near reception and the ski season can be quite good right through March, as the recent Nor’easters dumping inches of snow have demonstrated. Once the snow melts, the region is well-known for outdoor fun, including hiking and ziplining, as well as flea markets and antiquing, art galleries, wineries, and distilleries. Or relax in your room; once your friends and family see your photos of the Roxbury, they would understand why you decided to cocoon in there.

The author visited the Roxbury as a guest of the property.