Back in 1928, the club letterhead boasted "the best little golf club in the world where good folks get together and enjoy each other". Year after year this little missive has remained true of the club. 

In the early 1920's, Vermont golf towns Newport, Barton, and Derby already had courses. Meanwhile, the Orleans golfers played in the rugged Barton cow pasture. The men, however, wanted to find a way to not put money into a course leased by a farmer. A course that used cows as "fairway mowers." The local fairground offered them a flat meadow, surrounded by woods and a farmhouse, to build a golf course. The meadow became the links and the old farmhouse turned into a clubhouse. The Orleans Country Club course has come  long way. An old county road bisected the property that hosted fairs until the 1870s along with an oval racetrack ran that broadside to what is now the 12th tee. It also cut through the 14th green and across to the 16th tee into the fairways, leaving humps and ridges. Today, these pieces of history have resulted in slight uphill, downhill and side hill lies. Golfers 80 years ago eventually raised $9,550, and construction began on six holes in the meadow. They carved a "dog leg" out of the woods and connected it all to end in front of the farmhouse, which made a great makeshift clubhouse, complete with porches, a fireplace and locker rooms.