Robert and Margaret Martin and the 1936 founding
Robert and Margaret Martin built the Wagon Wheel Motel in 1936 with deliberate planning for the growing Route 66 traveler market. The Martins were Crawford County residents who had observed the rapid growth of automobile tourism along Route 66 during the highway's first decade and recognized the commercial opportunity in providing purpose-built overnight accommodation for cross-country travelers. The original construction was substantial — the main stone building and the surrounding stone cottages were built using local Crawford County limestone in a style appropriate to the rural Ozark setting.
The motor court design reflected mid-1930s accommodation practice. Detached stone cottages arranged around a central court allowed travelers to park their cars directly outside their rented room — a substantial convenience compared to the era's hotel format where travelers parked in shared lots and walked through public lobbies and corridors. Cottages were small but private: each unit had a bedroom, a small bathroom, and basic amenities at the level appropriate to mid-1930s travel.
The Martin family operated the motel through World War II and into the post-war Route 66 commercial peak. The 1940s and 1950s were the motel's strongest decades — Route 66 traffic was substantial, Cuba was a recognized overnight stop, and the Wagon Wheel's combination of distinctive stone-cottage architecture and convenient downtown location produced steady occupancy. Various ownership transitions occurred across the subsequent decades but the property continued to operate through Route 66's commercial peak and into the I-44 decline period.