Nestled in the rolling hills and lush valleys of New York’s Catskill Mountains, the stretch of road now known as Route 28, running from Kingston to Pine Hill, is more than just a scenic byway—it’s a testament to the vision and enterprise of the Winne family.
In the 19th and early 20th centuries, the Winne family not only played a pivotal role in constructing this vital artery through the Catskills but also leveraged their land holdings to establish a network of boarding houses and hotels that laid the foundation for the region’s tourism industry. Their legacy is woven into the fabric of the Catskills, where their properties welcomed travelers, artists, and adventurers, helping to transform the area into a beloved destination.
Building the Road to Opportunity
In the early days of the Catskills, before the region became synonymous with summer retreats and outdoor adventure, transportation was a significant barrier to development. The rugged terrain made travel difficult, limiting access to the natural beauty and resources of the area. Enter the Winne family, whose ambition and ingenuity led to the construction of the road that would eventually become Route 28. This thoroughfare, stretching from Kingston to Pine Hill, opened up the heart of the Catskills, connecting small hamlets like Mount Tremper, Woodstock, and Phoenicia to the broader world.
The road was a monumental undertaking, requiring significant resources and determination. The Winne family, with their deep roots in the region and substantial land holdings, were uniquely positioned to spearhead this project. Their efforts not only facilitated easier travel but also set the stage for economic growth, as the road became a lifeline for commerce and tourism. By creating this vital link, the Winnes ensured that the Catskills could welcome visitors from near and far, setting the stage for their own entrepreneurial ventures in hospitality.
The Winne Family’s Hospitality Empire
With the road in place, the Winne family capitalized on their strategic land holdings to establish a series of boarding houses and hotels that catered to the growing influx of visitors seeking the Catskills’ fresh air, scenic vistas, and cultural charm. These properties, scattered along Route 28 and its surrounding areas, became cornerstones of the region’s burgeoning tourism industry. Each establishment reflected the family’s commitment to hospitality, offering unique experiences that drew travelers from across New York and beyond. Below, we explore the key properties that defined the Winne family’s legacy.
Winne House in Mount Tremper, NY
Run by Davis Winne, the Winne House in Mount Tremper was a beacon of comfort for travelers exploring the heart of the Catskills. Nestled along the Esopus Creek, this boarding house offered a cozy retreat for those seeking respite after a day of hiking or fishing. Davis Winne’s establishment was known for its warm hospitality and prime location, making it a popular stop for visitors traveling along Route 28. The Winne House capitalized on the natural beauty of Mount Tremper, with its proximity to trails and scenic overlooks, helping to establish the hamlet as a destination in its own right.
West Shokan Hotel in Mount Tremper, NY
Cornelius Winne operated the West Shokan Hotel, another gem in Mount Tremper that catered to the growing number of tourists flocking to the Catskills. This hotel, situated in a picturesque setting, offered guests a blend of rustic charm and modern comforts for its time. Cornelius leveraged the hotel’s location near the newly constructed road to attract travelers heading toward Pine Hill or exploring the nearby Catskill Mountains along the Esopus Creek. The West Shokan Hotel became a hub for social gatherings, with guests enjoying the serene landscapes and the opportunity to connect with the local community. It is now underneath the Ashokan Reservoir. 🙁
Woodstock House in Woodstock, NY
In the vibrant artistic enclave of Woodstock, A.E. Winne ran the Woodstock House, a lodging that became synonymous with the town’s creative spirit. Woodstock, already gaining fame as an artists’ colony in the late 19th century, was an ideal location for a hotel catering to musicians, painters, and writers. The Woodstock House offered a welcoming environment where guests could immerse themselves in the town’s burgeoning cultural scene, from live music to art exhibitions. A.E. Winne’s establishment helped solidify Woodstock’s reputation as a haven for creativity, drawing visitors who sought both natural beauty and cultural enrichment.
Eagle Hotel in Kingston, NY
A.E. Winne, in partnership with J.S. Winne, operated the Eagle Hotel in Kingston, a bustling hub at the eastern end of Route 28. As the gateway to the Catskills, Kingston was a natural starting point for travelers, and the Eagle Hotel served as a grand introduction to the region. The hotel offered refined accommodations for its time, catering to both business travelers and tourists embarking on their Catskill adventures. The Winne brothers’ management ensured that the Eagle Hotel was a place of comfort and elegance, setting the tone for visitors’ journeys along the newly built road.
Pine Grove Villa in Mount Tremper, NY
J.B. Winne’s Pine Grove Villa in Mount Tremper was another standout in the family’s portfolio. This villa offered a more intimate experience, with its charming accommodations nestled among the pines. The Pine Grove Villa attracted guests seeking a peaceful escape, with easy access to the outdoor activities that defined the Catskills, such as hiking, fishing, and skiing. J.B. Winne’s attention to detail and commitment to guest satisfaction made the villa a beloved retreat for those looking to unwind in nature.
Winne’s Cottage in Mount Pleasant, NY
Operated by Mrs. Robert Winne, Winne’s Cottage in Mount Pleasant provided a cozy, family-oriented lodging option. This cottage-style accommodation was perfect for small groups or families seeking a home-away-from-home experience. Mrs. Winne’s warm hospitality and the cottage’s idyllic setting made it a favorite among visitors looking for a more personal touch. Its location along the Route 28 corridor ensured easy access to nearby attractions, further enhancing its appeal.
Winne Hotel in Phoenicia, NY
In the charming village of Phoenicia, C.C. Winne ran the Winne Hotel, a cornerstone of the town’s hospitality scene. Situated near the Esopus Creek and just minutes from Belleayre and Hunter Mountains, the Winne Hotel was ideally positioned to attract outdoor enthusiasts. C.C. Winne’s establishment offered a blend of comfort and adventure, with guests enjoying everything from tubing on the creek to skiing in the winter months. The hotel’s proximity to Phoenicia’s vibrant dining and shopping scene further cemented its status as a must-visit destination.
A Legacy of Tourism and Community
The Winne family’s contributions to the Catskills extended beyond their individual properties. By building Route 28 and establishing a network of hotels and boarding houses, they created a framework for tourism that continues to thrive today. Their properties were more than just places to stay—they were gateways to the Catskills’ natural wonders and cultural heritage. From the artistic vibrancy of Woodstock to the tranquil beauty of Mount Tremper and the adventurous spirit of Phoenicia, the Winne family’s establishments helped define the region’s identity as a premier destination.
The road they built, now Route 28, remains a vital lifeline, carrying visitors through the heart of the Catskills to explore its trails, waterfalls, and charming towns. The Winne family’s foresight in recognizing the potential of their land holdings and their ability to create welcoming spaces for travelers laid the groundwork for the region’s enduring appeal. Today, as visitors flock to the Catskills for hiking, skiing, and cultural experiences, they follow in the footsteps of those who stayed at the Winne House, West Shokan Hotel, Woodstock House, Eagle Hotel, Pine Grove Villa, Winne’s Cottage, and Winne Hotel—testaments to a family that helped shape a region.
