To get from New York City to Greenwood Lake required an economical and reliable car that could make the journey and return home. Fortunately, Greenwood Lake was filled with automobile service, repair, and maintenance stations that could guarantee that you could make the trip at 14 miles per gallon in the 1920s. A Model T had a 10-gal capacity in those days. When the U.S. developed a better system of roads after the First World War, drivers needed longer-range vehicles that could go the 50-mile distance. New sources of crude oil helped to reduced the price of gasoline, making both car ownership and car maintenance more affordable to the average consumer.

Otherwise, travelers took the ferry to the train in Hoboken and then hopped on the train to Greenwood Lake, which often had to stop and chase herds of cows off the tracks. Upon arrival they were greeted by a steamboat which took them to their favorite hotel on the lake. Train service was halted in the late 1930s, after The Depression, when road systems increased and cars became the preferred mode of transportation.