Following World War II, veterans returned to Sherwood to find their town dangerously cut off from the Portland area's transportation routes. Old Sherwood Town's reliance on the Southern Pacific Railway Company had proved to be a costly mistake. And so some of our veterans staged the most successful public relations campaign in Sherwood history. Playing off the popularity of recently produced Robin Hood movies, Sherwood Oregon's Robin Hood and Crew could not accept all the invitations they received to appear in other Oregon towns, including Portland. For the record, the original crew was composed of Wilber Shloneker, John Gibson, Bob Scheller, Pete Kowal, Don Dahlke, Ted Riech, and Don Cocheran (per Don Dahlke, who warned that the spellings are approximate. There were also some key players that do not appear on Dahlke's list: Ben Langston, Doc Stearn, Les Oyler, Floyd Johnson, James Ferry, and Lorn Drummond). Meanwhile, a group of archers, The Sylvan Archers, challenged the Nottinghamshire Archery Society to an annual archery match that began a tradition that survives to this day. NBC News reported on Old Sherwood Town's success in cementing ties with America's ally from the Great War.

There is a long association between the Robin Hood Legend and the military veteran. In 1381, when the bow and arrow was still state of the art, unemployed veterans rose up to demand a more democratic society in England. The most colorful moment during this rebellion was when Wat Tyler, a genuine Robin Hood type, walked up to the fourteen year old King Richard II and shook his hand and addressed him as though he were just another little kid. Tyler's impertinence cost him his life, but the Robin Hood ballads became very popular during the reign of Richard II. The Robin Hood icon became even more well established as a symbol of rebellion against oppression during the 15th Century, during the Wars of the Roses, when several prominent rebel leaders took the name "Robin" as a way of signalling their commitment to the poor and dispossessed of England. All this time, Robin Hood ballads were being generated that would become the basis for at least one Shakespeare play (Henry IV, Part One, wherein Sir John Falstaff and the Crown Prince of England, Henry VI, compete for the title of legendary greenwood thief.) as well as countless Hollywood movies.

The spirit of Robin Hood was an important motivating force in American history, and Sherwood remained an example of it well into modern times. To this very day there is an axiom stating that when the majority of Washington County voters go one direction, "Sherwood always votes No. " During the 1970s, the Sherwood City Council fought tooth and nail to stay out of Portland's Urban Growth Boundary. It was the massive pollution problems created by a local tannery that forced the town to belong to Portland's service district.