Mass timber has moved to the forefront of the North American construction industry, driven by demands for sustainable, efficient, and aesthetically pleasing alternatives to steel and concrete. Mass timber construction capitalizes on engineered wood products (EWPs), including glued-laminated timber (glulam), which is manufactured by laminating smaller wood sections together to create a massive timber element. While timber has long been used as a structural material, EWPs have enabled engineers to build larger and taller timber structures. Consequently, it is critical that their behaviour is well understood so that these structures are functional and safe for their occupants. While EWPs are highly manufactured, they are still composed of natural material, which leads to questions surrounding the influence of anomalies (e.g., knots, cracks, and finger joints) on their structural performance. Furthermore, because glulam beams are derived from smaller laminations of timber, they can be formed into complex shapes (e.g., curved beams), however, questions remain surrounding the structural behaviour of these complex elements. Finally, as the use of mass timber expands across North America, so too will the need to develop innovative strengthening solutions so that these structures can evolve and adapt to changing occupancies or address degradation. This research aims to address some of these challenges and is focused on two main themes. The first theme focuses on improving the fundamental understanding of the behaviour of glulam timber beams, including straight, curved, and deep beams. The second theme focuses on developing strengthening techniques for flexure critical and shear dominant timber beams using advanced composite materials. In all elements of this work, distributed fibre optic strain sensors are employed to provide unprecedented insight into the behaviour of glulam timber beams. Results of the study highlight the complexity of glulam timber as a material and the efficacy of using advanced composite materials to improve their strength.