This study was intended to measure construct validity for the Outward Bound Outcomes Instrument (OBOI) and to predict outcome achievement from individual characteristics and course attributes using multilevel modeling. A sample of 2,340 participants was collected by Outward Bound USA between May and September 2009 using the OBOI. Two phases of data analysis were conducted. Phase I was to validate the OBOI using both exploratory factor analysis (EFA) and confirmatory factor analysis (CFA). Phase II of the data analysis was to investigate the effect of both individual characteristics (i.e. age, gender, ethnicity, and scholarship) and course attributes (i.e. course length, course type, activity type and group type) on Outward Bound outcomes using multilevel modeling. A two-level model for each outcome variable was fitted. The Level 1 model described between-individual variability in the relationships of dependent variables, and includes all individual characteristic variables. The Level 2 model captured variance between course variability and includes all course attribute variables. Phase I results supported the theoretical design and provided support for the instrument's construct validity. While the Character Development and Leadership factors occurred as expected, the Service factor findings differed from the hypothesized outcome. Phase II analysis included a series of models that indicated two of the course attributes (Male Group and Course Length) accounted for more than 40% of the between course variance for all three dependent variables (Character, Leadership, and Environmental Service). Two out of four individual characteristics (Scholarship and Ethnicity) explained about 5% of the between individual variance for all three dependent variables. The results of this study provide an example of an evaluation procedure that provides relevant and adequate program accountability measures for adventure education programs. The results of this study not only provide useful information regarding how adventure education outcomes are achieved, but also suggest an improved way of conducting outcome evaluations to acquire scientific evidence on various program components and approaches. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]