History of The Roxbury Motel

The breathtaking beauty of the region and their close proximity to New York City have made the Catskill Mountains a popular destination for travelers since the nineteenth century.  The first major wave of visitors began when railroads were built, connecting the Catskills with steamships and trains that ran between New York City and Rondout (near Kington, New York). The rails reached Stratton Falls in 1871 and were extended to Roxbury the next year. Following the Great Depression and mirroring the ease of travel by automobile, a second wave tourism began after the Second World War and extending into the 1960s. The latter was primarily to the “Borscht Belt,” where luxury resorts spawned a generation of famous comedians and entertainers.

With the construction of the railroad, Roxbury received its own share of tourists, although it was never as densely populated and always more rural and bucolic than the Borscht Belt region, an hour and a half to the south.

At the height of the tourism boom in 1900, there were 35 hotels and boarding houses in Roxbury and nearby Grand Gorge capable of housing nearly 700 guests. Two-thirds were in Roxbury. But by the 1950s with the demise of rail travel, the advent of air travel, and the new affordability of air conditioning units in warmer tourist destinations, lodging in the Roxbury area had dwindled to only one establishment, the Roxbury Hotel.

In 1959 Bonnie and Gary Hinkley, local Roxbury residents with a family history in the area dating back many generations, opened the Plattekill Ski center which brought a renewed surge in tourism. To help serve skiers discovering the beauty of Roxbury for the first time and to the fill the void left by the demolition of the Roxbury Hotel, the Hinkley’ s in 1963 built the Roxbury Motor Lodge. The couple lived in a house next door to the Motor Lodge. In 1984 the property was sold to Frances McCardle, who turned the building into small apartments.

From 1984 to 2004 there were no conventional hotels or motels in Roxbury until Gregory Henderson and Joseph Massa purchased the former Motor Lodge and renovated it into The Roxbury, Contemporary Catskill Lodging, aka “The Roxbury Motel.”  The Hinkley’s house next door was converted into a check-in and common area, while the upstairs became an additional suite. The “strip motel” building adjacent to the house received a gut renovation with its nine units redesigned as ten.  On July 24, 2004 (Gregory’s 40^th birthday), The Roxbury Motel first opened its doors, ushering in a new age of tourism for the region.

In 2006, The Roxbury Motel broke ground on its first expansion, adding a new wing adjacent to the original motel along with a firepit/lounging deck and a spa with hot tub and sauna. At the time, Gregory and Joseph were slated to build a franchise hotel in neighboring Margaretville. But after a devastating fire destroyed their residence and most of their personal belongings and memorabilia, they re-thought their life goals and decided to take a risk with a new concept:  building one-of-a-kind theme rooms that were whimsical in nature without sacrificing quality and elegance. The goal was to provide a sense of wonder without becoming “kitsch.” In July 2007, seven new-construction theme rooms and suites debuted. Each paid homage to the films, TV shows, and cartoons of the 1960s and 70s, the era when the original Motor Lodge was built and roadside motels were in their heyday.

Two years later the Roxbury Motel broke ground on a second expansion, with nine more rooms and suites again showcasing the TV shows and films of the 1960s and 70s (and the owners’ passion for them). The new building was across the street from the existing motel. Opening in September 2010 the expansion included a much larger spa area with multiple treatment rooms, a relaxation and reading library, and a conference facility.  The building became known as The Roxbury North, while the original buildings across the street were dubbed The Roxbury South.

In 2011, The Roxbury Motel broke ground on its third expansion, the renovation of a house adjacent to The Roxbury North. The former residence was converted into a luxury cottage entitled The Archaeologist’s Digs, aka The Digs, drawing its inspiration from “Indiana Jones” and other archaeology/adventure/fantasy film franchises. The design of The Digs was to advance the theme concept to guest rooms and suites to a new level of experiential detail.  The Digs takes its guests on a journey through the treasures and collections of its archaeologist-creator via experiences, including secret passageways, hidden treasures, a Mayan Temple, and a bathroom shower featuring a 500-gallon saltwater aquarium housing Cleopatra’s sarcophagus There is also a full, gourmet kitchen.

In 2014 the popularity of The Digs led Gregory and Joseph to begin formulating the concept for The Roxbury at Stratton Falls.  The Digs taught them that there really is no such thing as “too over-the-top.” So long as elegance, customer service, and of course, cleanliness remained top priorities, there was no limit to the public’s appetite for a quality themed-lodging experience.

In October 2017, two miles down the road from the existing motel, ground was broken for The Roxbury at Stratton Falls. The new project was to include the renovation of an 1848 Italianate mansion into seven guestrooms, each with an ensuite bathroom and a design scheme inspired by the rich history of the Stratton Falls locality itself. In addition, plans were drawn up for construction of eight stand-alone 800-900 sf, two-bedroom, two-bathroom, two story, “tower cottages” with” fairy-tale-esque” themes. Other features were to include conversion of an existing carriage house into a manager’s residence; a swimming pool and lounge area; and a spa with hot tub, sauna, relaxation area, treatment rooms, common activity room, and parking for guests. Finally, the property would include a system of spectacular trails and observation decks surrounding the property and its biggest attraction: a 50-foot waterfall that cascades into a beautiful scenic pool.

All of these dreams are now reality.

We invite you to explore the History of Stratton Falls section of this website to learn more about The Roxbury at Stratton Falls – our sister property to The Roxbury Motel.