High-rise mass timber buildings require beam end connections to maintain the fire resistance rating of the beam. Connections where a glulam beam ends bear directly onto a supporting glulam column are commonly utilized because they reduce cost, require only simple CNC fabrication, meet the desired architectural aesthetic, and have high load carrying capacity. In addition, a properly designed bearing connection can achieve a 1hr-to-2hr fire rating. A beam to column bearing connection designed and fire tested for a high-rise building project in the United States is presented in this paper. An assessment of the bearing area required to support the load under fire conditions required detailed review of the scientific literature to understand how the thermally impacted timber ahead of the char front reduces the perpendicular-to-grain mechanical properties at the bearing interface. An estimate of the reduced perpendicular-to-grain stiffness and strength at the bearing area was used to design the connection. Two 2 hr fire tests to ASTM E119 were performed to experimentally validate the design assumptions. This paper concludes with a discussion of how engineering guidance for bearing type connections exposed to fire can be further developed.