State DOTs has started including phased deployment of Connected and Automated Vehicle (CAV) technologies in their transportation plans and programs. While theoretical analyses have indicated significant benefits of CAVs for improving system performance, actually deploying these technologies at existing or upgraded highway facilities concerns more than technological issues. This study reported a large-scale simulation-based real-world case study initiated by the Federal Highway Administration in collaboration of the Virginia Department of Transportation to investigate CAV early deployment opportunities on Interstate 66 outside the Beltway. Discussions include applicable technology bundles, infrastructure upgrades, operational strategy enhancements, technology algorithms and implementation, and simulation results for managerial insights.