Harnessing the power of the 400th anniversary of the arrival of enslaved Africans to the U.S. in 1619, scholars have designed a mindfulness-based learning experience that supports communities with taking a contemplative walk through history to process our collective past. This presentation explores the use of a 4ft x 20ft timeline as a contemplative learning tool that engages communities in mindful listening for the purpose of deepening their understanding of entrenched racial and socio-economic inequality in the U.S. This presentation highlights practices, personal anecdotes, and findings of a contemplative qualitative inquiry on the facilitation of the timeline experience with over 3,000 people throughout the country. Looking at the efforts of creating a more compassionate and inclusive society with the longstanding legacy of structural inequality in the U.S.A, there has been a hunger for learning processes that bring people together to engage in difficult conversations on issues concerning diversity, inclusion and social justice. In addition, the present socio-political struggles the country faces has generated unprecedented levels of polarization. The Contemplating 400 Years of Inequality experience has leveraged these social forces along with mindfulness-based and contemplative practices to invite communities to re-imagine how we can transcend both implicit bias and structural inequality in order to develop a more compassionate society.