The history of Highland began on the shores of the Hudson River in 1754, when entrepreneur Anthony Yelverton started a sawmill, later followed by a brickyard, store, and ferry service to Poughkeepsie. During the 19th century, steamboats made regular stops near Yelverton's settlement. Starting around 1830, riverfront businesses began to relocate to the 'high land' above the river, and a new Highland business district was born. The West Shore Railroad was completed in 1883, with a station at the riverfront. The area was called Highland Landing. The Poughkeepsie-Highland Railroad Bridge, now the Walkway Over the Hudson, was completed in 1888, and in 1897, a trolley line began operation from Highland Landing up to the Highland village and, from there, westward. Highland had a new claim to fame as the 'Gateway to Ulster County.'