The Chequessett Yacht and Country Club (CYCC) was established in 1929, eleven years after the dike at the mouth of the Herring River was built (1908) to restrict tidal flow.

Several low-lying greens and fairways of the golf course have been wet or flooded following heavy rains or other conditions raising the water table – particularly holes #7 and #8, which are traversed by Mill Creek. (See the image.) But the Herring River project would permanently flood five fairways and greens. Therefore, for the project to proceed, the planners would have to mitigate this problem. Negotiations commenced as early as 1999, when Cape Cod National Seashore Superintendent Maria Burks and Seashore ecologist John Portnoy met with the CYCC Board of Governors to discuss increasing tidal flow in the Herring River.

A deal was eventually struck whereby the Herring River project would solve the existing problem of wet fairways and greens by mitigating the permanent flooding that would result from the project. But this solution would be a double-edged sword because the golf course would have to close operations for two years during the extensive construction required. The negotiations were long and sometimes contentious. The Herring River Restoration Committee eventually signed a memorandum of understanding with the CYCC, which was drafted four years earlier in 2017, pledging that the HRRC would seek funding and permits for the work needed to mitigate the golf course flooding.

The committee made good on its promise to seek funding to mitigate the project's flooding of the CYCC golf course. On February 9, 2021, the Wellfleet Select Board approved by a vote of 5-0 the signing of an agreement between the town of Wellfleet and the CYCC that would allocate $6.7 million for flood mitigation, most of which will be used to elevate the five low-lying tees, fairways, greens, roughs, and sand traps that would be flooded by the tidal restoration. The CYCC Golf Course Construction Budget totals $5.7 million for the renovation, with an additional $975,000 to compensate the club for loss of business during the estimated two years of construction.

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