Wide-area database replication technologies and the availability of content delivery networks allow Web applications to be hosted and served from powerful data centers. This form of application support requires a complete Web application suite to be distributed along with the database replicas. A major advantage of this approach is that dynamic content is served from locations closer to users, leading into reduced network latency and fast response times. However, this is achieved at the expense of overheads due to (a) invalidation of cached dynamic content in the edge caches and (b) synchronization of database replicas in the data center. These have adverse effects on the freshness of delivered content. In this paper, we propose a freshness-driven adaptive dynamic content caching, which monitors the system status and adjusts caching policies to provide content freshness guarantees. The proposed technique has been intensively evaluated to validate its effectiveness. The experimental results show that the freshness-driven adaptive dynamic content caching technique consistently provides good content freshness. Furthermore, even a Web site that enables dynamic content caching can further benefit from our solution, which improves content freshness up to 7 times, especially under heavy user request traffic and long network latency conditions. Our approach also provides better scalability and significantly reduced response times up to 70% in the experiments.