In September of 2000 the Historical Society staged its first Walk in the Park. This fundraiser evolved into a very popular annual event until 2011, where community actors and actresses portrayed historic Highlands characters near their graves in Memorial Park.
Over eleven years Walk in the Park featured such well-known historic figures as golf-legend , who opened Highlands' first major golf course the year before his grand slam in 1930, here portrayed by Tony Potts; and medical pioneer , who established one of North Carolina's first TB sanatoria (known in Highlands as "Bug Hill") in 1908, here portrayed by Becky Schilling.Glenda Bell portrayed Helen Wright Wilson, founder of Helen's Barn, where buck dancing, square dancing, and mountain clogging thrived in Highlands for 50 years, amalgamating summer and winter residents alike into a single class of foot-stomping revelers; and Derek Taylor played renowned photographer George Masa, who photographed almost 100 scenes of Highlands and its surroundings in 1929.
Stell Huie played Native storyteller Herman Wilson, who charmed his listeners for years with fascinating tales of early Highlanders who survived hard times because they grew and made what they needed; and Brian McClellan was Dr. Alexander Anderson, who discovered the method for producing what became known through the Quaker Oats Company as "Puffed Wheat" and "Puffed Rice.
Other historic characters portrayed in Walk in the Park have been midwife Ida Henry (Jane McNairy), eponymous founder of the Highlands library Ella Hudson (Becky Schilling on the left), police chief Ed "Bennie" Rogers (Charles Edwards on the right), Biological Station director and scientist Thelma "Doc" Howell (Bonnie Powell), educator and botanist Prof. Thomas G. Harbison (Ted Shaffner), town mayor during the Moccasin War H. M. Bascom (Wiley Sloan), town founders Samuel Kelsey and C. C. Hutchinson, corundum miner Charlie Jenks (Thomas Craig), and many, many more.