Shepard Hills Golf Club sits in the rolling Catskill Mountain foothills near Roxbury, New York, a region that experienced a modest golf boom in the early twentieth century as resorts and private clubs emerged to serve visitors from New York City. The course was designed by Finley Shepard, a figure whose work in the area reflects the era's approach to routing golf holes through natural terrain with minimal earth-moving. The layout takes advantage of the property's elevation changes and wooded corridors, characteristics common to Catskills golf courses where designers worked within the constraints of hillside farmland and forest edges. The routing moves through varied topography, with holes that climb and descend across the property's natural contours. Players encounter approach shots to elevated greens and tee shots from high ground that reveal the surrounding mountain landscape. The course reflects a straightforward design philosophy typical of its period, emphasizing strategic placement over length and rewarding golfers who navigate the terrain thoughtfully rather than relying solely on distance. Shepard Hills operates as a semi-private facility, serving both members and daily-fee players in a region where golf remains a seasonal pursuit. The club maintains a low-key atmosphere consistent with rural Catskills golf culture, where the focus remains on the game itself rather than elaborate amenities. The course provides a representative example of mountain golf in upstate New York, offering a traditional layout shaped by the land's natural features.