This paper will present my current work on the Hajj Trail, a digital teaching tool which aims to present the cultural history of the early modern Ottoman World through an interactive and accessible historical simulation. The project aims to bring the experiences found in early modern pilgrimage narratives to students through an interactive digital platform. The format of The Hajj Trail simulation builds off the style of the 1970s educational simulation 'The Oregon Trail' that generations of American public-school students played during their elementary education. The Hajj Trail expands on the concepts of that older educational tool and repurposes it for an educational introduction to the cultural history of the early modern Islamic World – and in particular the Ottoman Empire. The simulation takes students along the Ottoman caravan route from Istanbul to Mecca where they encounter the beauty and difficulty of traveling in the early modern world as sourced from early modern travel and pilgrimage narratives themselves. The most prominent examples being the travelogues of Evliya Çelebi, Yusuf Nabi, Abu Salim al-Ayyashi, Qutb al-Din al-Nahrawali, Ambrosio Bembo, and Richard Pococke among others. The paper will examine educational outcomes from the use of this teaching tool in classroom. Moreover, I will explain how the project came together, the utility of the user-friendly coding tool Twine, and how similar projects could be put together for the study and teaching of the Islamic World in the future.