An experimental study has been conducted to examine the flow field about and the wake behind truncated cylindrical obstacles of varying height, which are towed through a fluid with a free surface in a rotating system. The results show the development of a vortex street-type wake downstream of the obstacle for retrograde (westward) flows, even for very small ratios of obstacle height to water layer depth. For short obstacles, a pronounced backward flowing jet is observed, which impinges on the Taylor column from downstream. Prograde (eastward) flows are found to have a meandering wake that extends farther than eight obstacle diameters downstream and do not exhibit backjetting or vortex street formation. Upwelling is believed to occur within the side boundary layers of the Taylor column, which could play a significant role in deep water production in the ocean.