The area around Lake, Main, and Water Streets was an early industrial center of the community that became Penn Yan, beginning with David Wagener’s sawmill on the south bank of the Crooked Lake Outlet and a second sawmill on the north bank in 1801. Along the seven-mile outlet, about 40 industrial enterprises and 12 dams included grist mills, sawmills, carding machines, fulling mills, tanneries, plaster mills, distilleries, woolen and cotton factories, spoke factories, shingle factories, and triphammers. After the Crooked Lake Canal opened in 1833 just north of the outlet, the ravine became busy with industry and commerce, and when the steamboat Keuka began operating in 1835, mainly towing canalboats on the lake, the Keuka Lake area was linked by water to wider markets as lake boats and canal boats met along the outlet between this area and the boat launch upstream from the Liberty Street Bridge. By 1844, wheat, corn, barley, oats, butter, cheese, eggs, dried apples, dried peaches, plums, potatoes, and other products were shipped to Seneca Lake and beyond on the canal. By the end of the 1800s, nine dams remained, along with three grist and planing mills in Penn Yan, and the only surviving water-flow regulation is the dam beside the Main Street Bridge. During the canal era, canalboats passed under a cantilever at the Randall & Eastman Warehouse to load through trap doors, and that warehouse is the only canal building left in Penn Yan. By 1875, two malt houses stood on the Water Street side of the outlet and a cooperage stood on the Lake Street side, and when another Water Street warehouse was remodeled in 1893, workers found a sign reading “S.S. Hutchins, keeper of the Fugitive Home.” After the canal was abandoned in 1870, businessmen bought the right of way and completed a rail spur for the Penn Yan & New York Railway in 1884; it later became the Fall Brook branch ending at the foot of Keuka Lake, and the Main Street Bridge was completed that year to allow locomotives to pass. Flooding in 1972 damaged the tracks beyond repair, leading to abandonment in 1974, and about 1979 Yates County and the village of Penn Yan bought the right of way from the railroad, with the county’s portion later turned over to the Friends of the Outlet. Across the outlet, the former Penn Yan Gas Light plant was built in 1899 on the site of the H. Tuttle and son Malt House, converting coal into gas for illumination, and a lengthy environmental cleanup there was completed in 2020. Other businesses along the canalway included a Dairymen’s League creamery and Walker Bin, built as a sash and molding planing mill in the late 1800s and run by steam engine.