The lodge that is now Paradise Trail Lodge began as a hotdog stand along the old Highway 26, the then main thoroughfare through the Mount Hood National Forest. After initial success, the enterprising hotdog vendors chose to build a permanent establishment, and in 1925, the Oregon Trail Tavern was built. For over fifteen years, the Oregon Trail Tavern served as an eatery, lodging (three cabins were also built on the property), and gas station. Hard to imagine, when one stands on what is now a quiet property on a dead-end road with very little traffic. In the years that followed, the tavern closed down permanently.
Eventually, the chalet was used by the Oregon City Ski Club for a number of years before becoming Paradise Trail Lodge and Campground, named for the nearby popular hiking trail, Paradise Park Trail.