Viscoelastic flow around a confined cylinder at high Deborah numbers is studied using microfluidic channels. By varying fluid properties and flow rates, a systematic study of the roles of elasticity and inertia is accomplished. Two new elastic flow instabilities that occur at high Deborah numbers are identified. A downstream instability of disordered and temporally varying streamlines is observed at a Deborah number above 10. This instability is a precursor to an unsteady vortex that develops upstream of the cylinder at higher Deborah numbers. Both instabilities occur at moderate Reynolds numbers but are fundamentally elastic. The size and steadiness of the upstream vortex are primarily controlled by the Deborah and the elasticity number.