In September 1903, Ernest Machado, a 35-year old Boston architect, his older brother Jose, brother-in-law Alfred Whitman and 3 park rangers, headed out from Canoe Lake on a 12-day canoe trip through the Algonquin wilderness. In the summer of 2013, over a century later, the author and four companions repeated this trip with view to contrast and compare the experiences. Earlier that summer, two young women attempted a marathon trek to paddle to Brent and back in less than 24 hours Three different canoe tripping experiences that are connected in time in so many ways. In the oral history tradition, this narrative provides insights into how canoe tripping in Algonquin Park has changed and yet not changed over the last 110 years.