In this paper we present the design of a Variable Structure Interacting Multiple Model (VS-IMM) estimator for tracking groups of ground targets on constrained paths using Moving Target Indicator (MTI) reports obtained from an airborne sensor. The targets are moving along a highway, with varying obscuration due to changing terrain conditions. In addition, the roads can branch, merge or cross-the scenario represents target convoys along a realistic road network with junctions, changing terrains, etc. Some of the targets may also move in an open field. This constrained motion estimation problem is handled using an IMM estimator with varying mode sets depending on the topography, The number of models in the IMM estimator, their types and their parameters are modified adaptively, in real-time, based on the estimated position of the target and the corresponding road/visibility conditions. This topography-based variable structure mechanism eliminates the need for carrying all the possible models throughout the entire tracking period as in the standard IMM estimator, significantly improving performance and reducing computational load. Data association is handled using an assignment algorithm. The estimator is designed to handle a very large number of ground targets simultaneously. A simulated scenario consisting of over one hundred targets is used to illustrate the selection of design parameters and the operation of the tracker. Performance measures are presented to contrast the benefits of the VS-IMM estimator over the Kalman filter and the standard IMM estimator, The VS-IMM estimator is then combined with multidimensional assignment to gain "time-depth." The additional benefit of using higher dimensional assignment algorithms for data association is also evaluated.