History & Culture · Hudson Valley
Hillsdale's East Gate Toll House Remembers the Columbia Turnpike
Hillsdale's East Gate Toll House recalls a rare tollgate tied to the 1799 road between Hudson and Massachusetts.
Published June 24, 2026 · Last verified June 24, 2026
Hillsdale’s East Gate Toll House turns road history into something you can actually picture. Town materials say the toll house was added to the State and National Register of Historic Places in early 2016.
The same town account ties the building to a 1799 act creating a turnpike from Hudson to the Massachusetts line and says the toll house was built around 1799. That is practical history, not just a plaque: Hillsdale once sat on a commercial route carrying goods, especially wool, between rural Columbia County and Hudson’s market.
The East Gate Toll House gives Hillsdale a little of its old road sound back. It suggests wagons, tolls, market trips, and a town that made sense because people and goods had to cross the hills in particular ways. Modern Route 23 feels different when that older turnpike story is still visible.
For a small Columbia County place, that is a strong bit of identity. Hillsdale is more than scenery and a road to somewhere else; it has a surviving building that remembers how movement, commerce, and hill-town geography once worked together.