This paper introduces Guess the Age of Photos, a web platform engaging users in estimating the years of historical photographs through two gamified modes: Guess the Year (predicting a single image's year) and Timeline Challenge (comparing two images to identify the older). Built with Python, Flask, Bootstrap, and PostgreSQL, it uses a 10,150-image subset of the Date Estimation in the Wild dataset (1930-1999). Features like dynamic scoring and leaderboards boost engagement. Evaluated with 113 users and 15,473 gameplays, the platform earned a 4.25/5 satisfaction rating. Users excelled in relative comparisons (65.9% accuracy) over absolute year guesses (25.6% accuracy), with older decades easier to identify. The platform serves as an educational tool, fostering historical awareness and analytical skills via interactive exploration of visual heritage. Furthermore, the platform provides a valuable resource for studying human perception of temporal cues in images and could be used to generate annotated data for training and evaluating computer vision models.