During seismic events, mass timber gravity connections must be able to accommodate the induced lateral deformations while still maintaing their load bearing capacity. Large-scale experimental testing can demonstrate and provide data or different connection configurations and numerical simulations can further inform the behaviour of these connection under lateral demands. However, there is a lack of data available for benchmarking numerical testing modelling. This paper will summarize a comprehensive large-scale testing regime performed at Oregon State University on five glulam beam-to-column connections, three custom designed connections and two pre-engineered connections. Each connection was tested under both monotonic and cyclic loading demands and the data from one of the connection tests was used to develop preliminary numerical modelling techniques for glulam beam-to-column connections. The tests demonstrated that all of the connections were able to be tested to 7.2% drift in the monotinic test and 4% drift in the cyclic test without losing load bearing capacity. The experimental testing regime develop data on maximum force demands in the connections, connection rorations, and connection stiffnesses that were used to characterize the connections on a scale of pinned to fixed connections.