Bridlemile's recorded history begins in the early 1850s, when Donation Land Claims carved the West Hills into private holdings. Albert Kelly was the first recorded landholder in what would become the neighborhood. For decades the area went by the name West Union, developing slowly along its creek-cut ravines and wooded slopes. The name changed in 1911, when Dr. John Powell created a bridle path across the hillside for his wife to ride, and the neighborhood took its identity from that trail. The historical Glencullen community, named for Captain John Cullen, occupied part of what is now Bridlemile and once had its own Southern Pacific station, providing brief rail access in the 1920s. One farmhouse predating 1860, built by Andrew Tigard (whose brother Wilson Tigard gave his name to the city of Tigard), still stands within the neighborhood, connecting Bridlemile to the earliest era of West Hills settlement. Fifteen properties now appear on Portland's Historic Resource Inventory, a count that reflects how much the neighborhood preserved through gradual, terrain-constrained development.