This study uses observed data and a numerical simulation to examine the generation of thermally driven flows across the Colorado mountain barrier on meso-β to meso-α scales. The observations were collected from remote surface observing systems at exposed mountaintop locations throughout the state of Colorado, over the summers of 1984–88, as part of the Rocky Mountain Peaks Experiment (ROMPEX). The data show the development of a recurrent circulation system across the Colorado mountain barrier, operating on a diurnal timescale. From the observations, the basic structure of the flow system appears as a daytime inflow toward the highest terrain, and a nocturnal outflow away from it. However, when examined in detail, the flow system exhibits more unusual behavior, especially west of the barrier crest. Here, winds in the early evening are occasionally observed to onset abruptly from an easterly direction, generally counter to the upper-level winds. Observations from ROMPEX for 26 August 1985 are used to provide comparison data for a numerical simulation with the Regional Atmospheric Modeling System (RAMS). This three-dimensional case study experiment is initialized with data from the National Meteorological Center and incorporates two-way interactive grid nesting. From the observed data and case study simulation, four distinct phases of the regional-scale circulation system have been identified. In the development phase, a deep mountain-plains solenoid is generated through terrain heating along the Front Range. This circulation system transforms in the late afternoon transition phase into a westward-propagating density current (WPDC). The third phase, called the “density-current propagation phase,” occurs as the WPDC moves westward across the mountains, leaving in its wake strong southeasterly flow at the mountaintop level. This current appears to be the cause of the peculiar easterly component winds found in the ROMPEX mountaintop observations along the western slope. In the final late-night adjustment phase, the WPDC dissipates near the western edge of the Colorado mountains and a steady southerly flow evolves over the high mountain terrain. This southerly flow is the steady response to the differential heating that develops between the low-lying plains and the intermountain region.