Journey through the outskirts of Greater Kendall Square on I | Cleveland Circle, past the fabled 77 Massachusetts Avenue entrance to MIT and across the Harvard Bridge into the City of Boston. You then pass through Kenmore Square, a block from Fenway Park, home of the Boston Red Sox, then across the Masspike and into Brookline. High quality biking infrastructure is then with you most of the way through Brookline – through St Mary’s Circle, Coolidge Corner and Washington Square as you wind up at Cleveland Circle. At Cleveland Circle, you are a stone’s through from the Chestnut Hill Reservoir.