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The Greatest Music Cities to Road Trip to From Toronto

What’s a road trip without reason? There’s nothing like hitting the road to see live music, whether it’s the festival circuit or just making the trek to catch one of your favourite artists in their hometown.

Here are six music cities worth a road trip to from Toronto.

Austin, Texas

South By Southwest has evolved to become one of the world’s premier music events. Top artists and industry leaders from around the world descend upon Austin, Texas every March to experience the best in music, films, and interactive media. There’s also Austin City Limits, which runs over two consecutive weekends in October and has featured the likes of Radiohead, LCD Soundsystem, and Wilco.

It’s a long ride south, but worth the venture for the lure of good old southern hospitality along the way.

Travel Commitment: You’re looking at a 24-hour drive from Toronto, or roughly 2,600 km.

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Nashville, Tennessee

“Music City USA” has long been an attraction for country music fans, but Nashville has become a mecca of sorts for emerging punk rock artists. The rise of bands like Diarrhea Planet, JEFF the Brotherhood, Music Band, Daddy Issues, and Natural Child have helped the city become a destination for more than just cowboy boots and bourbon. Jack White has set up headquarters for Third Man Records there, and Canadian-owned and operated Dine Alone Records also keep offices in Nashville.

Nashville’s country music history is rich, with spots like The Grand Ole Opry, Music Row, and the Country Music Hall of Fame all on the must-see radar for music enthusiasts.

Travel Commitment: Toronto to Nashville by car runs about 12 hours or 1,250 km. Don’t sleep on the hot chicken!


Chicago, Illinois

Chicago offers a little something for the music fan in everyone. The city that’s produced hip hop heavyweights Kanye West and Chance the Rapper lays claim to some of the biggest events on the festival circuit.

The Chicago Blues Festival has been running since 1984, and the June festival’s list of past performers reads like a who’s who of the greats. Blues not your thing, breeze through the “Windy City” for one of the major summer festivals like Lollapalooza or the Pitchfork Music Festival.

Travel Commitment: It’s like a day at the office, driving to Chicago takes approximately eight hours (835 km).



New Orleans, Louisiana

The birthplace of jazz is the best place to take in the genre live. Whether it’s the numerous clubs that line Bourbon Street, the wealth of street performers, or the New Orleans Jazz and Heritage Festival that runs from late April to early May, “The Big Easy” offers the ultimate jazz experience year-round.

Travel Commitment: It’s a long haul at 20 hours (2,100 km), but offers plenty of attractions on the way down south.


Halifax, Nova Scotia

The provincial capital of Nova Scotia is probably best known in music circles for its celtic roots, but Halifax is no slouch in the modern music scene. Artists like Joel Plaskett, Matt Mays, Sloan, and Wintersleep have all called Halifax home at one point in their respective careers.

While you can always find a good local band rocking one of the various venues like The Seahorse Tavern, The Company House, and Bearly’s, many of the pubs around the city offer live house bands playing more traditional “East Coast” music. Every music fan should make a trip to the iconic Marquee Club at some point, and the Halifax Pop Explosion is a great festival that’s especially accessible given the walk-ability factor of the city.

Travel Commitment: It’s roughly 17 hours (1,800 km) from Toronto to Halifax.


Montreal, Quebec

New Orleans wasn’t the only place where jazz was thriving in the 1920s. Much of Montreal’s reputation as a music city was born out of its history in the Jazz Age, when it became a Canadian hub for jazz musicians. Since then, the city has developed quite the underground music reputation, birthing indie artists like Arcade Fire, Grimes, Stars, The Stills, and Wolf Parade. On the festival side, Montreal’s Osheaga in August is a must-see event for every modern music fan.

Travel Commitment: It’s but a mere six-hour (540 km) drive by car, so what are you waiting for?

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