Chequessett Yacht & Country Club sits on Cape Cod in Wellfleet, Massachusetts, occupying land that overlooks Wellfleet Harbor and the tidal flats characteristic of the Outer Cape. The course was designed by Van Kleek and reflects the modest scale and intimate character typical of many Cape Cod layouts from the early-to-mid twentieth century. The property's coastal setting means golfers encounter steady breezes and the visual backdrop of marshland and water that defines this stretch of the Massachusetts coastline. The routing makes use of the natural topography, with holes playing across gently rolling terrain and through stands of pitch pine and scrub oak. The course measures relatively short by contemporary standards, placing emphasis on accuracy and course management rather than length. Several holes offer views toward the harbor, and the layout's connection to the water and surrounding landscape gives it a distinctly Cape Cod feel. Chequessett functions as a traditional yacht and country club, serving both boating and golfing members in a community known for its fishing heritage and summer colony atmosphere. The club maintains a low-key, family-oriented character consistent with Wellfleet's reputation as one of the quieter towns on the Outer Cape. The alternate tees provide flexibility in course setup and allow for varied playing experiences across different skill levels and conditions.