Timber covered bridges have a long history of use in North America and have served as vital transport connections to remote communities and critical economic resources since the earliest European settlers spread across the continent and many are still in use today. There are various recommendations and guidelines for design and evaluation of these unique bridges, however there is a distinct omission amongst all the methodologies. When analysing, the effect of the cladding is largely neglected, except for when calculating the wind loads to be applied, where the cladding is not explicitly modelled, and the load is transferred directly to the trusses. There is significant variability in modelling techniques of a covered bridge which can often lead to unrealistic results in the analysis as compared to reality. Understanding the impact of the cladding will serve to decrease the discrepancies between the models and reality and improve the engineering understanding of the behaviour of these bridges. A series of numerical models have been developed using finite element software based on the structural geometry of the Larwood Covered Bridge in Oregon, U.S.A., which is a Howe truss bridge. Cladding is applied in different arrangements: full coverage, eaves-level slit openings, intermittent windows, large opening and full coverage with no cladding stiffness. The models explore the impact of these arrangements on the displacements and internal member forces of the Larwood Bridge under wind loading. The study demonstrates that accounting for the cladding decreases displacements in critical structural elements by between 10–70% depending on the configuration. The cladding arrangement also impacts the load distribution to the structural elements, with height and size of opening leading to changes in element stresses. Variations with greater degrees of cladding coverage, and thus stiffness, transfer tensile forces from the vertical tension elements of the truss to the bottom chord.