The streets along this walk owe their names to the very first summer cottages in Toronto (Castle Frank), a hill that looked like a sugarloaf (Drumsnab), two families that were among the first residents in the area (Hogarth and Playter), and the Duke of Wellington (Wellesley). One of the oldest Toronto neighborhoods, Cabbagetown has rows of interesting old houses and a famous cemetery. The view of the downtown towers from Broadview Ave. is one of the best in the city.

Highlights

• Castle Frank Subway Station
• 5 Drumsnab Rd., 1834: An early Toronto residence that overlooked a quiet Don Valley.
• 316-334 Wellesley St., Armstrong Terraces, circa 1890: Look for the matching towers on opposite sides of the street.
• 156 Winchester St., Lamb House, circa 1860s
• 200 Winchester St., Necropolis Cemetery, 1850: Many famous Torontonians are buried here, including William Lyon MacKenzie and William Peyton Hubbard, Toronto’s first Black alderman.
• 201 Winchester St., Riverdale Farm: In 1978, this urban farm replaced the Riverdale Zoo, which was a popular attraction from 1894 to 1974.
• St. Matthew’s Lawn Bowling Clubhouse, circa 1906: In 2009, this heritage building was moved from Gerrard St. to its present position on Broadview Ave.
• 469 Broadview Ave., Cox House, circa 1800: This house may well be the oldest family home in Toronto, built by John Cox, a soldier and storekeeper.
• 58 Hogarth Ave., 1875: One of the first houses built in what was a very rural neighborhood before the streets were laid out.
• 28 Playter Crescent
• Chester Subway Station