The present study assessed the Bailey Bridge’s condition and investigated its adaptation as a permanent structure, targeted the Acrow Bailey Bridge in Japan. Field diagnostic loading experiments were performed under various loading conditions, such as dynamic and static loading tests. The onsite data were obtained using a transducer, friction strain gauge, target measurements for the image processing approach, and accelerometer. From the field measurements, the deflection and stresses of the bridge were found to operate within the linear elastic region. The bridge was then accurately modeled based on the in situ geometric configuration of the bridge, and Finite Element Analysis was performed. The model’s accuracy was validated with the onsite data under the linear elastic domain. The model was deployed to check for resistance of critical members. A nonlinear analysis based on the linear and nonlinear buckling method was performed to determine the subject bridge’s Serviceability Limit State and Ultimate Limit State. The results showed that the first out-of-plane eigenvalue buckling analysis could monolithically assess bridge members. Further, the study established digital twin models resolve for historical data through in situ modeling measurements. Therefore, the findings obtained in this study highlight the bridge’s Structural Health Condition, bearing capacity, and propose a framework for adaptation as a permanent structure.