Toronto’s Best Places for Fun in 2026

As an Italian expat resident in Toronto since 2018, I've noticed the city is always evolving, and this year's 'Best of Toronto' list reflects those changes. From new trails and trivia nights to indie moviehouses and live music venues, there's plenty to explore. Here are some highlights that are worth your time, whether you're a long-time resident or a visitor.

Best Trivia Night: Hemingway’s in Yorkville
For trivia enthusiasts, Hemingway’s in Yorkville is a standout. With a packed lineup of themed events covering movies, music, and pop culture, it’s a must-visit. The Jonas Brothers might even drop by, so keep your eyes peeled!

Best New Trail: East Don Trail
The East Don Trail, while a bit of a wait, is now open and stunning. With gorgeous forests, riverside views, and a four-level switchback ramp, it’s perfect for a leisurely walk or ride. The trail is a sign of the city’s ongoing commitment to green spaces.

Best Indie Moviehouse: Fox Theatre
The oldest operating movie theatre in the city, Fox Cinema, continues to shine with an incredible slate of films, a fantastic vibe, craft beers, good wines, and tasty popcorn. It’s the perfect place to unwind after a long day.

Best Live Music Venue: The Concert Hall
Once the legendary Rock Pile, now The Concert Hall, is back and better than ever. Located at 888 Yonge St., it offers a solid comeback with a modern look and a rich history. It’s a true gem for live music lovers.

Best Arcade Bar: Tilt on Queen West
Tilt is the go-to spot for classic arcade games. With unlimited play on a rotating roster of arcade classics and a solid selection of pinball machines, it’s a fun night out. Plus, they’re expanding to the Annex with a new venue called Bumpers.

Best Cold Plunge: Othership in Yorkville
For a unique and communal experience, head to Othership in Yorkville. The facility offers a diverse range of classes and a spa-like atmosphere. It’s a great way to start the day with a cold plunge or end it with a relaxing session.

These spots are just a few of the many exciting places that make Toronto a dynamic city. Whether you're exploring new areas or revisiting old favorites, there's always something new to discover in Toronto. Stay tuned for the latest updates and trends in the city's ever-changing landscape.