Originally named Wautonga Cemetery, a Native American word meaning Oak Forest or Oak Wood, was the original name of this cemetery. The first eight acres of land that would become Oak Grove Cemetery were likely purchased in 1861, by Deacon Samuel T. Smith as a private venture. However, the cemetery contains the remains of people who died before 1861, such as that of David Darst, murdered by William Watts in 1852. Because the land was largely sandy and flat, the people of early La Crosse continued to use their pioneer burial grounds, a more scenic location, near the corner of 3rd and Badger streets, to bury their loved ones. Smith soon sold his investment to C. S. Strasberger, who enlarged the cemetery to 32 acres in 1869. Gradually the land began to be used for burials. Because the cemetery wasn't recognized by any singular church or religious group, little interest went into care or improvements of the land. Several newspaper articles from the 1860s make mention of the poor conditions of the area, where broken fences allowed farm animals to wander into the cemetery. Hogs dug up the fresh, muddy graves, cows tipped over tombstones and local citizens themselves thought nothing of taking apart the surrounding fences to use as firewood. However, it was really the interest and dedication of local lawyer Joseph W. Losey that brought the neglected land out of a state of chaos. Losey spent many years devoted to beautifying the cemetery, raising funds from private donors and encouraging the city council to contribute to the cause. With his efforts, grottos were constructed, gravel walkways were laid out, and a fountain erected. Although little of Losey's improvements still exist today, he will be forever remembered and memorialized by the arch monument built in his honor in 1902 which welcomes mourners and visitors into the main entrance of the cemetery on La Crosse Street.

Another addition to the cemetery in recent years was the crematorium. Although it remains independent of the cemetery itself, the Oak Grove Crematorium was built on space that is leased from Oak Grove Cemetery and originally was the site of the cemetery sexton's house. The need for a crematorium was a much disputed topic in La Crosse for many years. As early as the mid 1880's, plans were drawn for a crematorium in Oak Grove but the idea was scrapped. Bodies had to be shipped to Milwaukee via railroad to be cremated. Local interest in cremation again became widespread in the late 1970's, and the independent group calling itself the Oak Grove Crematorium Ltd., led by President Sally Cremer and directors Marjorie Nixon, Carroll Gundersen, Diana DeVoll, Jake Buchel, Dave Baptie, Ray Sundet and Dr. Sigurd Gundersen Jr., was successful in hiring the architectural firm of H. S. R. & Associates and contractor H. E. Martell in constructing a crematorium in Oak Grove Cemetery. The crematorium finally came to be in early 1979. Helene B. Traister was the first cremation in early March 1979. The area was leased to the People's Mauseolum Company doing business under the name Oak Grove Crematorium Ltd. The crematorium proved to be viable and in November 1981 the Oak Grove Cemetery Association took over the assets of the group. A new crematorium was constructed in 1989 as part of the current office complex and chapel. Although the cemetery has endured several vandal attacks in the past decade, the scenic cemetery remains a constant tribute and source of pride to the citizens of La Crosse. In September, the La Crosse County Historical Society hosts the "Silent City" program, bringing to life the history of La Crosse through re-enactors of some of the cemetery's citizens.