Field-scale and wind tunnel experiments were conducted in the 2D to 6D turbine wake region to investigate the effect of geometric and Reynolds number scaling on wake meandering. Five field deployments took place: 4 in the wake of a single 2.5-MW wind turbine and 1 at a wind farm with numerous 2-MW turbines. The experiments occurred under near-neutral thermal conditions. Ground-based lidar was used to measure wake velocities, and a vertical array of met-mounted sonic anemometers were used to characterize inflow conditions. Laboratory tests were conducted in an atmospheric boundary layer wind tunnel for comparison with the field results. Treatment of the low-resolution lidar measurements is discussed, including an empirical correction to velocity spectra using colocated lidar and sonic anemometer. Spectral analysis on the laboratory- and utility-scale measurements confirms a meandering frequency that scales with the Strouhal number St = fD/U based on the turbine rotor diameter D. The scaling indicates the importance of the rotor-scaled annular shear layer to the dynamics of meandering at the field scale, which is consistent with findings of previous wind tunnel and computational studies. The field and tunnel spectra also reveal a deficit in large-scale turbulent energy, signaling a sheltering effect of the turbine, which blocks or deflects the largest flow scales of the incoming flow. Two different mechanisms for wake meandering—large scales of the incoming flow and shear instabilities at relatively smaller scales—are discussed and inferred to be related to the turbulent kinetic energy excess and deficit observed in the wake velocity spectra.