Tropical cyclones (TCs) of varying shapes, sizes, and intensities form in nearly every ocean basin and can potentially impact heavily populated areas, threatening human life and property. As a TC moves poleward, it can interact with a variety of synoptic-scale features, which results in either the dissipation of the TC or a transition into an extratropical cyclone (EXTC) through the process of extratropical transition (ET). Given an ideal synoptic-scale setup, a TC can transition into a fast-moving and rapidly developing EXTC, which could extend TC-like conditions such as strong surface winds and intense rainfall over a broad area at high latitudes. In recent years, three TCs, Irene (2011), Sandy (2012),and Andrea(2013), transitioned to EXTCs while approaching the middle latitudes and subsequently impacted the Northeast as EXTCs. In order to analyze the ET of these TCs, the cyclone phase space, developed by Hart (2003), was utilized. This product aids in determining the structural evolution associated with ET in which a symmetric, warm-core TC transitions to an asymmetric, cold-core EXTC. Changes in the structure, motion, and intensity of TCs during ET are highly dependent on the midlatitude environment into which the TC moves. A variety of factors contribute to the intensity of the resultant EXTC, including the overall large-scale pattern, track of the TC, time of year, as well as the intensity of the TC and the frontal system with which the TC interacts. Synoptic-scale features were analyzed for three phases of evolution throughout the ET process: tropical phase, transition period, and post-tropical phase. The TCs were not influenced by the upper-level flow until shortly after the onset of transition. It was not until the mid-waypoint of the transition period when the TC circulation was incorporated into the flow and began to exhibit baroclinic features. Due to differing tracks and TC intensities, the synoptic-scale features analyzed in each phase vary among each case in the tropical phase and beginning of the transition period. There are generally more similarities in synoptic-scale features between the cases toward the end of the transition period and in the post-tropical phase. As these EXTCs impacted the Northeast, reports of heavy rainfall and strong surface winds spanned across vast areas of the region.