In 1969, the Pinedale Boat Club held their first race at Fremont Lake. 50 years later, the Fremont Lake Sailing Regatta is considered one of the top events in the country, earning the nickname "Little America's Cup".

"Most sailors in the western states have come to know that the second weekend of August is the annual pilgrimage to Fremont Lake," longtime skipper Jason "The Pirate" Essington told Pinedale Online. "To fellowship with other nautical types, commiserate about the trials of a 3 month sailing season, tell sailing lies, and occasionally sail their craft in a circle on one of the most spectacular sailing venues in the country."

Essington is one of the event organizers and founder of the Karma Pirates, who describe their motto as "achieving inner peace through limited sobriety". The two-day regatta features five races with teams competing for the prized Regatta Burgee, a flag awarded to the fastest, and slowest, vessels.

"The race is sort of like musical chairs for boats," Terry Allen wrote for Pinedale Online. "There were cowboy whoops and “yeehaw’s” all over the fleet as the wind almost threw everyone off their feet. I crashed into one side of the cabin or the other until I learned to anticipate the changes, but I cracked a few body parts pretty good in the process."

Located just outside of Pinedale, Fremont Lake is the second-largest natural lake in Wyoming, over 12 miles long and a 1/2 mile wide. The glacial lake is also the seventh-deepest lake in the country, with a maximum depth of 610 feet. Along with a Lakeside Lodge and Marina, the lake also features a restaurant, picnic tables, and a sandy beach.