Renewed interest in urban forestry has resulted in significant public investment in trees during the past few years, yet comprehensive urban forest monitoring programs are uncommon. Monitoring is an integral component of a program to sustain healthy community forests and long term flows of net benefits. Volunteer-based monitoring will promote continued public involvement and support in community forestry. To overcome constraints to monitoring in urban environments, programs must be personally relevant, socially desirable, scientifically credible, and economically feasible. A three-tiered monitoring approach is presented. Canopy cover analysis documents net gains and losses in regional urban forest cover. Simplified detection monitoring uses trained volunteers to better understand tree population dynamics, while intensive monitoring characterizes urban forest functions and stressors. Implementation of an urban forest health initiative to develop, place, and evaluate monitoring programs is advocated.