There are many speculations as to just exactly how Jeffrey’s Bay ended up with its name. There was a ship trading captain that plied his trade along the East Coast of Africa during the 1800s and sometime in 1840 the crew of his vessel came down with scurvy. To save his crew Captain Jeffrey’s landed his ship on the now main beach of Jeffrey’s Bay, he later returned 10 years later and bought erven 1, 2, 9 and 10 for 79, here he build his home on what is now the corner of Woltemade and Jeffrey’s Streets. The prominent Reilly family moved to Jeffrey’s Bay in 1928 and it is reported that they used the original timber from Captain Jeffrey’s ship to build their home.

There are other speculations that the name came from a prominent trader in the area in the 1850s, or from a whale hunter from St Helena, who used JBay as a harbour and trading post.

The land that Country Feeling is standing on today belonged to the Reilly’s who build a Wimpy Bar on it during the 1960s which was demolished in 1964 to make place for a double story residential flats that included a tea garden and gift shop on the same property.

In the 1850s the well known Jeffrey’s Bay Hotel was build which was renamed the Savoy in 1937, it was demolition in 1968 along with a part of Jeffrey’s Bay history.

The legendary John Whitmore, also know as the father of South African surfing, was travelling the Garden Route of South Africa during the 1950s on a business trip and came across what is considered to be one of the best surfing waves in the world, the rest is history. Today thousands of surfers from across the globe make the pilgrimage to Jeffrey’s Bay to pit them against the best right hand point break in the world and to pay homage to this awe inspiring wave. Jeffrey’s Bay also hosts the international Billabong Pro competition which is the half way point to determine the next world surfing champion.