Walking Tour: Historic Dogtown­ – A Walk Back in Time

Sunday, October 18, 2026 10:00 a.m. – 12:00 p.m. Babson Boulder Parking Cherry Street, Gloucester, MA 01930 CAM Members $15, Non-Members $25. Registration Required On Cape Ann, the name “Dogtown” conjures up many things—vast woodlands and trails; stone walls and cellar holes; tales of witches and widows; an ill-fated bullfighter; pastures, picnics and blueberries; a sea of rocks. Dogtown is all of these things and more. But first, it is a place where proud people once lived and worked, at the center of Gloucester, for nearly 150 years—until it became “Dogtown” and died out. This tour will take you down the main roads of this early settlement, to meet some of the people, see where they lived and hear their stories. You will learn how Dogtown got its name, why people left, and how it has changed in the 200 years since the last house came down. You will hear about writers and artists who were inspired here, and reservoirs that were built here. Finally, you will see some of the inspirational word-boulders along the trails that are the lasting legacy of entrepreneur and philanthropist Roger Babson (1875-1967), and a symbol of the enduring nature of this special place called Dogtown. The Historic Dogtown walking tour is almost three miles and will take approximately two hours. The route is over hiking trails that are generally easy, but uneven, with rocks and roots underfoot. The terrain is up and down throughout, over gentle hills. Hiking attire and closed footwear advised; walking poles are useful. Bring water and insect repellent, as they are not supplied. Please note that this tour is not suitable if you have mobility concerns. Image Credit: Marsden Hartley (1877-1943). Summer Outward Bound, Gloucester, 1931, oil on board. Collection of Cape Ann Museum. Gift of the estate of Robert L. French, 2009 .