Tollgate is an unincorporated community in Umatilla County, Oregon, United States. It lies between Weston and Elgin on Oregon Route 204. The area was first homesteaded by David J. Woodward. After co-forming the Summerville and Walla Walla Road Co., Woodward purchased land near the headwater of Lookingglass Creek (later dammed in 1922 to create Langdon Lake). A road leading east from the city of Milton and the city of Walla Walla, Washington to the city of Summerville and the Grande Ronde Valley crossed Woodward's property. Woodward installed a toll gate across this portion of the road and charged travelers a fee for access through the gate. The toll road was frequently used as a means to move farm products from Union County to Umatilla County and Walla Walla County.