In the following paper we explore the dynamics of single colloidal particles and particle aggregates in a counter-propagating cavity-enhanced evanescent wave optical trap. For this study we make use of Fabry-Perot like cavity modes generated in a prism-coupled resonant dielectric waveguide. The advantage of using this type of optical structure is that there is an enhancement in the electric field of the evanescent at the sample surface that may be used to achieve greater coupling to colloidal particles for the purposes of optical micromanipulation. We demonstrate an order of magnitude increase in the optical forces acting on micrometer sized colloidal particles using cavity enhanced evanescent waves, compared with evanescent wave produced by conventional prism-coupling techniques. The combination of the enhanced optical interaction and the wide area illumination provided by the prism coupler makes it an ideal geometry for studying the collective dynamics of many particles over a large area. We study the different type of ordering observed when particles of different sizes are accumulated at the centre of this novel optical trap. We find that for large particles sizes (greater than 2μm), colloid dynamics are primarily driven by thermodynamics, whilst for smaller particles, in the range of 200-600nm, particles ordering is dictated by optical-matter interactions. We suggest a qualitative model for the observed optically induced ordering occurs and discuss how these results tie in with existing demonstrations of twodimensional optical binding.