Around 1870, the Ulster & Delaware Railroad started offering comfortable passenger travel between Kingston and Phoenicia, with many stops in between. This allowed Olive residents to compete with the great mountain house resorts like The Tremper House, which could accommodate 275 guests. Family homes became boarding houses during the tourist season, often accommodating 10 to 30 guests. Soon Olive entrepreneurs built large boarding houses with rooms for 100 or more. Unfortunately this expansion happened just years before the railroad was demolished for reservoir construction. Olive's boarding house history can be explored through their advertisements in railroad travel guides and postcards.