Jefferson Park, Chicago Community Area #11 is 10 miles northwest of the Loop. Nicknamed, the “Gateway to Chicago”, farmers once came from far and wide to sell their goods in Jefferson, named to honor Thomas Jefferson. Jefferson’s ideal location began as two Native American trails, grew to include the area’s earliest toll plank roads, and was thereafter augmented by rail and commuter lines. Today the area has a population of over 40,000, a tremendous amount of green space, historical homes and buildings throughout, and a namesake park on the National Register of Historic Places. Hop on your bike to visit an extra and intra-urban experience that barely feels like Chicago at the same time that it typifies it.