Toronto native Jeffrey Kishner ’01S (MBA) shares plenty of picks for the perfect long weekend.
Meet your guide
Toronto native Jeffrey Kishner ’01S (MBA) is a finance and operations executive and founder of the consulting firm Epoche Insights. He’s also an active University of Rochester alumnus and a member of the Canada Network Leadership Council and the Simon Alumni Network.When Kishner isn’t working, he’s spending time with his wife, Jennifer Gotlieb, and their two children.
Known as one of the world’s most multicultural and cosmopolitan cities, Toronto draws nearly 28 million visitors each year for its culinary delights, sports culture, historic landmarks, and vibrant arts and cultural scene.
“Less than four hours north of Rochester, Toronto is really a city for everyone,” says Jeffrey Kishner ’01S (MBA), who was born and raised there. “It’s easy to explore by foot, bus, streetcar, or subway, and it offers an extensive network of trails, parks, and urban forests perfect for outdoor enthusiasts.”
Kishner, one of 1,000-plus alumni who call this city home, offers an insider’s insights into a few of its diverse neighborhoods, plus a few more of his favorite spots.
Downtown and the Harbourfront
Start off at the iconic CN Tower and, if you are up for thrills, brave its EdgeWalk, the world’s highest full-circle, hands-free walk. Harnessed 116 floors above ground, you can take in unparalleled views of the city. From there, venture over to the Hockey Hall of Fame for a deep dive into Canada’s favorite sport. Don’t miss the chance to get a photo with the Stanley Cup—a true national treasure. Sports fans might also want to catch a Blue Jays, Raptors, or Maple Leafs game, depending on the season. Insider tip: plan well in advance, especially for hockey games, as tickets can be notoriously hard to come by.
For dining, Gruppo Terroni offers authentic Italian cuisine in a historic bank building. For an extra-special experience, ask to see one of the old vaults. Or try contemporary Canadian fare at Canoe Restaurant, which boasts stunning city views. Next, explore the Harbourfront area, home to the Power Plant Contemporary Art Gallery and many family-friendly activities. Cap off the day with a short ferry ride to the Toronto Islands. This chain of small islands offers breathtaking skyline views, the Centreville Amusement Park (ideal for kids), and an array of beaches, parks, and trails.
The Distillery District and the Market
The Distillery District is a former industrial complex from the early 1800s that has been transformed into a pedestrian-friendly area with shops, restaurants, and breweries. Kishner recommends strolling some of the area’s historic cobblestone streets, too, including Colborne Street, known as the best-preserved street in Toronto’s Heritage District. Next, head to the St. Lawrence Market and order up one of Toronto’s signature dishes: the Veal Sandwich at Uno Mustachio. Cap off the day at the Rooftop at the Broadview Hotel, which offers great food and drink options, and more great views of the skyline.
Chinatown and Kensington Market
Explore the Frank Gehry–designed Art Gallery of Ontario, showcasing Canadian artists like Tom Thomson and Emily Carr and the Group of Seven along with the world’s largest collection of Henry Moore sculptures. Then visit the nearby Kensington Market, full of specialty food shops, eclectic restaurants (Kishner recommends Rasta Pasta for Jamaican fare), and vintage clothing stores. For cheese lovers, don’t miss Cheese Magic or Global Cheese.
Be sure to check out nearby Chinatown, too, known for its walkable streets and authentic cuisine. Kishner’s pick: Sunny’s Chinese restaurant.
Yorkville and Bloor Street West
The Bloor-Yorkville neighborhood offers a blend of galleries, shops, and cafes. It’s also the place for celebrity sightings. Films like My Big Fat Greek Wedding and The Shape of Water were shot in Toronto, which, in addition to Vancouver, is known as the “Hollywood of the North.” Visit the Royal Ontario Museum, too, featuring Daniel Libeskind’s crystal-like architectural addition, and dine at Fat Pasha for Middle Eastern food or ONE Restaurant, a contemporary hotspot.
If you have time. . .
Catch a show at the Second City, the legendary comedy club that launched Mike Myers, John Candy, Dan Ackroyd, Martin Short, Eugene Levy, and others. Plan to visit Ossington Ave., too, to find one of Kishner’s favorite places: Bang Bang Ice Cream & Bakery. His top pick: London Fog, a blend of Earl Grey tea and vanilla. For more great food, dine at Mamakas for Greek fare or the Pho Rùa Vàng Golden Turtle for its legendary Vietnamese pho. Save time for a drink at the Painted Lady or Sweaty Betty’s Bar.
Kishner, an avid concert goer, also recommends taking in a show at the Budweiser Stage, an amphitheater offering skyline views, or at the historic Massey Hall, where he’s seen Bob Dylan, B. B. King, and Neil Young. For a more intimate experience, check out Danforth Music Hall, the Horseshoe Tavern, or History, owned by the Canadian rapper Drake.
Deciding when to go?
If you plan ahead and don’t mind crowds, attend the Toronto International Film Festival, held every September. June is packed, with the Luminato Festival, Toronto’s International Festival of Arts and Ideas; Pride Toronto, one of the world’s largest Pride events; and North by Northeast, a music and arts festival modeled after Austin, Texas’s South by Southwest. In July, experience Caribbean Carnival (also called Caribana).
Says Kishner: “The carnival’s parade is a must-see.”
This story appears in the fall 2024 issue of Rochester Review, the magazine of the University of Rochester.
