The existence of Happy Hollow was spear-headed by eleven prominent Omaha businessmen led by Mr. Erastus A. Benson (the founder of the small community of Benson in North Omaha). On April 2, 1907 these men held the first stockholder meeting and adopted the Articles of Incorporation. Curiously, the very first resolution by these first Directors of Happy Hollow Club was to prohibit the selling of any form of alcohol on the club grounds. As years passed the club was dubbed the "Grape Juice Club." This did not deter the growth of the club as the membership mounted rapidly and steadily.
The Directors purchased the original clubhouse located at the site that is now known as Brownell-Talbot School from the J.N.H. Patrick family for the sum of $30,000. This was considered quite a bargain as the purchase price included two massive homes that cost the Patricks $67,000 to build and eleven acres of land. The Patricks were quite prominent in Omaha society and entertained quite often and rather lavishly. References were made frequently referring to their home as "Happy Hollow House." It is stated in one article concerning the forming of the club that: "The name Happy Hollow will be retained, preserving the name of a place for many years the scene of cultured hospitality and its many pleasant associations." The club first opened its doors on July 20, 1907.
For the Golf Course and other Field sports the Directors negotiated a fifteen-year lease on 90 acres just west of the clubhouse. The Directors failed to obtain an option on the land as the extension of a lease would have been only temporary and at a prohibitive price.
As the expiration of the lease on the Golf Course neared, the Directors began their search for a new home for Happy Hollow. In 1921 the clubhouse was sold to Brownell Hall for $100,000. A temporary arrangement was made with Brownell to share the buildings with the Happy Hollow members. Brownell would conduct school during the regular school year and the Happy Hollow Members would have use of the facilities during the summer months. On September 16, 1922 the Directors settled on a lease/purchase of the current Happy Hollow site. This new site included a 27-hole golf course and the clubhouse. The new course was open for play October 31, 1924 and the Clubhouse celebrated a formal opening on May 30, 1925. The formal dinner dance was by reservation only and strictly limited to members and their families. The cost was a whopping $2 per person.
Like all successful clubs, Happy Hollow has undergone many face-lifts and additions throughout the years. The club's most recent endeavors have been by far the most involved and most beneficial. In 1987 the club began a program to renovate the entire golf course. The initial phase was to construct three new golf holes to facilitate a program whereas the club would renovate three of the original holes each year until complete and at the same time provide the membership with eighteen holes of golf during the construction program. The final phase of golf course construction was completed in the fall of 1994. As if the golf course construction program was not enough, 1992 saw the beginning of a new project of unprecedented proportion. This project included demolishing and replacement of the pool, golf pro shop, tennis pro shop, cart barn, the east end of the clubhouse and the entire interior of the clubhouse. The project of replacing and renovating these facilities and adding new amenities like an exercise and fitness center, all new tennis court surfaces, expanded parking facilities, new practice putting green and all new furniture and fixtures cost over six million dollars. The end product of the years of golf course and building construction provided the membership with the premiere club in Omaha.