This study presents an experimental investigation on the effects of winglets on the near wake flow around the tip region and on the tip vortex characteristics downstream of a 0.94 m diameter three-bladed horizontal axis wind turbine (HAWT) rotor. Phase-locked 2D particle image velocimetry (PIV) measurements are performed with and without winglets covering 120 deg of azimuthal progression of the rotor. The impact of using winglets on the flow field near the wake boundary as well as on the tip vortex characteristics such as the vortex convection, vortex core size, and core expansion as well as the resultant induced drag on the rotor are investigated. Results show that winglets initially generate an asymmetric co-rotating vortex pair, which eventually merge together after about ten tip chords downstream to create a single but nonuniform vortex structure. Mutual induction of the initial double vortex structure causes a faster downstream convection and a radially outward motion of tip vortices compared to the baseline case. The wake boundary is shifted radially outward, velocity gradients are diffused, and vorticity and turbulent kinetic energy levels are significantly reduced across the wake boundary. The tip vortex core sizes are three times as big compared to those of the baseline case, and within the vortex core, vorticity and turbulent kinetic energy levels are reduced more than 50%. Results show consistency with various vortex core and expansion models albeit with adjusted model coefficients for the winglet case. The estimated induced drag reduction is about 15% when winglets are implemented.