In one embodiment, an agricultural system includes a tool bar configured to couple to a tow vehicle. The tool bar is configured to support at least one row unit assembly. The agricultural system also includes a lift assist assembly coupled to the tool bar such that rotation of the tool bar relative to the lift assist assembly about a vertical axis is blocked. The lift assist assembly is configured to provide lifting support to the tool bar. The lift assist assembly comprises a frame, one or more rolling elements configured to contact a surface of a field, and one or more telescoping members configured to adjust a configuration of the lift assist assembly along at least one of a lateral axis, a longitudinal axis, and the vertical axis.