Highland Golf Club occupies rolling terrain in Shelton, a small city in the lower Naugatuck River Valley of southwestern Connecticut. The course was designed by Frank G. Gates, a prolific architect active in the early twentieth century who worked primarily throughout New England and the Mid-Atlantic states. Gates designed or redesigned dozens of courses during his career, often creating layouts that made efficient use of available land while incorporating the natural contours of New England's glacially-shaped landscape. The routing at Highland takes advantage of the property's elevation changes and wooded character typical of this region of Connecticut. The course features tree-lined fairways and greens that reflect the design principles of the era in which it was built, with strategic bunkering and green complexes that reward accurate approach play. The layout moves through varied terrain that includes both open and forested sections, providing a mix of hole styles and shot requirements. Highland serves as a traditional member club in the Shelton community, maintaining the kind of unpretentious atmosphere common to many established New England clubs of similar vintage. The course provides a straightforward test of golf without excessive length, relying instead on shot placement and course management. It represents a typical example of early American course architecture adapted to the rolling, wooded landscapes of southern Connecticut.