“There are deeper gorges, greater streams and higher mountains but in no other place is the combination so blended into a harmony so perfect as to form such tempting bits for the camera or the brush.”

– “The Switzerland of America”, Edward F. Bigelow

Callicoon Hills old image

The History Of Callicoon Hills

Steeped in History

Before New York was New York, and Upstate was Upstate, America’s first wilderness beckoned. Dutch frontiersmen settled into the Hudson Valley, drawn to the abundance of timber, riverbanks, rolling hills, and wild turkeys – so many in fact that it became our town’s namesake.

Though the centuries have evolved wilderness to Woodstock, the majestic landscapes and rolling hills of the Hudson Valley continue to captivate travelers through generations as a cure-all for city-life.



While difficult to mark an officially beginning of our property, the Boarding House can be traced back to the turn of the century. Under a different name but the same wrap-around porch, the Wenzel Boarding House was home to acres of farmland on the west side of the Catskills with apartments held by the workers that helped the small town thrive.

Transitioning from a private estate to a hospitality holding shifted as gracefully as the other transitions of the times. The Progressive Era shifted trade towns to cosmopolitan cities, horses replaced by early automobiles, and the draw to the Western Catskills went from business to leisure – and stayed that way.

In the 1940s, the Hill family acquired the property and started the process of upgrading it from a boarding house to Hill’s Villa – a luxe vacation resort with additional buildings, an on-site kitchen, and new facets, while the restorative mountain air and leisurely pace as its calling card.

No longer a single manor house, the resort dropped the “villa” but added an alpine creek-fed pool and reintroduced themselves to the Catskills. The popularity of our signature pool led to the arrival of Terrace Hall, perhaps the only Catskills addition that doesn’t mind being put in the corner of our 23-acre expanse.

Callicoon Hills old image
Old Image


The 1960’s brought on the famed “Borscht Belt” era which came to be a defining aspect of vacationing in the Catskills. Resorts, bungalows, and summer camps continued to draw thousands from the crowded streets of New York City and the introduction of “all-inclusive” properties became the popular majority.

While innovative enough to still be an offering in hospitality today, the concept of being all-inclusive and inclusive-to-all became not only a Catskills characteristic, but one we use as a compass to this day. Discrimination might have been the graceless push that made resorts like ours landmarks, but creating the sense of belonging and authenticity is at the helm of our community and Callicoon experience.


Food for Thought

Arguably one of the most important gifts of living on the East Coast is the food and Hill’s was no different. In a tale for the ages, the executive chef of the property caught the eye of Marie Hill, daughter to the proprietors. Together, the newly minted couple because the unofficial yet charismatic hosts of the resort, saying “We provide the magnificent setting, facilities, companions… then let you set your own pace.”

The connection to history, hospitality and culinary excellence has remained our guide throughout the past few decades as we have become Callicoon Hills. As one of the last remaining mainstays that has seen Upstate New York through all of its seasons since 1905, our dining room has hosted countless dinners, our halls house countless memories made, and we look forward to welcoming you in the years to come.

Callicoon Hills