Among the neighborhood’s art-minded hotels, the Gladstone is the most interactive, with shows, classes, and ongoing events. The 37 rooms, all designed by local artists, have breathed new life into the 128-year-old icon, which filmmaker Christina Zeidler took over in 2003 and revitalized in 2005. The Victorian landmark, named for its avenue (in turn named after four-time Canadian Prime Minister William Gladstone), has been a gathering spot for over a century. And it was home to legendary Toronto characters like cowboy Hank Young, who became a fixture at the hotel as a country singer in 1961 and manned the hand-operated elevator from 2005 to 2009, and Peter Styles, former host of Karaoke Night, with applause sign in hand. The legend of Hank lives on in a framed photo in the stairwell en route to the second floor.
The Gladstone continues to push the boundaries of community and culture with creative events like its educational workshop series, Get School’d, and its annual alternative design event, Come Up to My Room (CUTMR), which runs alongside the city’s Interior Design Show. Begin your stay in this architectural gem with a drink at the Café or Melody Bar (that is, if you’re not first thrust into Fameless Karaoke Night).