This beautiful location just west of Dering’s Inn was originally a 12-acre private picnic grounds with twelve hundred feet of lake frontage.

Prior to 1879 George Ross and his brother James became interested in the lovely Pleasant Point Picnic area while they would stay at the Oakwood Resort down the road. The Oakwood was becoming very crowded, and the brothers felt that Dartford could use another resort accommodation. On November 22, 1879, the Ross brothers bought the Pleasant Point property from Charles A, Mather.

At the time that the brothers purchased the property they operated an insurance company in Chicago. James would stay in Chicago and run their insurance business and George would come up to Dartford and develop their resort. In the Spring of 1880, George built a 60×32 building that was quickly expanded to 130 feet long. Later seven tiny cottages were added to the original building. The hotel could accommodate over two hundred guests at its peak. An amusement hall, billiard room, bowling alley, tennis courts, boat rentals, and riding stables were all added later to provide enjoyable entertainment for all. A 60-acre farm was developed across Seminary Road (Illinois Ave) to provide fruit, vegetables, butter, milk, and eggs for the resort.

The last operator of Pleasant Point Hotel was George Mapps, who rented Pleasant Point Hotel along with running the Sherwood Forest Hotel. The end of Pleasant Point Hotel came in 1928 when a fire raced through the dry old wooden building and leveled it so quickly that guests and staff barely made it out with their lives.

Heritage History of Green Lake p127