The total number of operating dairy farms in the US has decreased by 74.1% over the past 25 years, dropping from 155,339 in 1992 to just 40,219 in 2017. As milk prices have fallen and become more volatile, profit margins have tightened, causing farmers to leave the business due to low profitability. Some Vermont farmers are currently looking for new economic strategies. One approach has been to transition from conventional to organic production in order to take advantage of better prices and new market opportunities. In order to make production decisions, farmers need accurate financial information on the costs and benefits of the various options available. Since 2004, UVM Extension has collected panel data on organic dairy farms in Vermont to help meet this growing need. As a part of UVM's long-term organic dairy profitability research, this study analyzed 10 years of financial panel data (2006-2017) from an unbalanced panel of approximately 40 organic dairy farms in Vermont. For article 1, a multivariate fixed effects regression model was used to identify key factors influencing farm profitability and estimate their effects on Return on Assets. Variables related to feeding management, farm management, farm characteristics, input costs, and year were shown to be significant. For article 2, industry wide milk price trends were compared with descriptive statistics on Vermont organic dairy profitability outcomes across a 3-year period (2015-2017) in order to test the hypothesis that recent price shifts have a had a noticeable effect on farm profitability. Despite limited data for 2017, results indicated a study-wide reduction in ROA in line with national market trends. In identifying management and market factors associated with profitability, this thesis provides valuable decision-making information for farmers interested in switching to organic. Results suggest that feeding management and milk quality improvements can improve profitability outcomes on Vermont farms. Vermont farmers will also benefit from the updated cost of production and financial performance data presented here. Evidence from this thesis also supports a need for new supply management policies and a more nuanced approach to organic dairy profitability research.