This paper presents millimeter wave propagation measurements in New York City and an analysis of signal outage at 28 and 73 GHz using similar spread spectrum sliding correlator channel sounders that employed high gain, directional steerable antennas (24.5 dBi gain antennas at 28 GHz and 27 dBi gain antennas at 73 GHz) at both the transmitter and receiver. Three identical transmitter locations were used for both the 28 and 73 GHz campaigns, while the 73 GHz campaign included two new TX locations. The 28 GHz campaign tested 25 receiver locations for each of the three transmitter locations, and the 73 GHz campaign tested 27 receiver locations in various combinations with the five transmitter sites. Overall, 75 TX-RX location combinations were tested at 28 GHz and 74 TX-RX combinations were tested at 73 GHz, with T-R (transmitter- receiver) separation distances up to 425 m. The maximum transmit power was 30 dBm at 28 GHz and 14.6 dBm at 73 GHz. Our analysis shows that the estimated outage probabilities at 28 and 73 GHz for the cellular communication scenario are 14% and 17%, respectively, and is 16% for the 73 GHz backhaul scenario.