In the nearly 40 years since the Little Italy BIA was founded, the neighbourhood has become a hub of activity. Trendy restaurants and bars line Ossington Avenue, ranked #14 on Time Out’s 2022 list of “the 33 coolest streets in the world.”
Despite its stylish reputation, Little Italy and surrounding area boasts a range of options for music lovers to enjoy a night out — from DJs to singer-songwriters.
For roots-inclined music fans, there are a few local venues. The most well-known is The Dakota Tavern, at Ossington Ave/Dundas St. The Dakota is a small venue with warm lighting and a rustic, homey vibe. Local artists play on a low stage, adding intimacy for a great listening room and a fun, lively party space. The club has a 130 person capacity, but being a basement makes it cozier. Artists who’ve played The Dakota Tavern include Blue Rodeo, Ron Sexsmith, Kathleen Edwards, Jason Collett and more.
The Painted Lady, a small bar with a saloon-like atmosphere and an eclectic range of live shows, is nearly kitty-corner to the Dakota. You can find musicians playing roots, rock, or jazz, or see a burlesque performance or a DJ. There’s an open mic night every Monday at 8 p.m.
For a roots music option on College Street (east of Bathurst St.), there’s The Cloak and Dagger Pub, an established Irish bar for over two decades. Like a true Irish pub, The Cloak and Dagger is dark and cozy, with a solid beer list. They’ve hosted many roots acts, including bluegrass performances and Celtic music for St. Patrick’s Day.
The Little Jerry is special because few bars design their space around their sound system. It opened in late 2019, located west of The Cloak and Dagger on College St. Thankfully, it survived the pandemic, and the business is thriving. The concept of The Little Jerry is inspired by Japan’s jazz kissa, which are cafes designed for playing and listening to jazz records. DJs spin records of all genres at The Little Jerry, and audiophiles will appreciate the quality sound from their high-end system.
Monarch Tavern, established in 1927 and located at 12 Clinton St., south of College, is in the heart of Little Italy. The Monarch is two levels, with a bar/music venue on the main floor and an old-school pub atmosphere above, appealing to fans of the Imperial Pub at Yonge/Dundas. The Monarch hosts all kinds of music, from dream pop to folk. They host karaoke every Thursday at 10 p.m. A bonus is Bitondo’s Pizzeria across the street, a popular, cash-only pizza joint.
You’ll find The Garrison, the “older sibling” of The Baby G, on Dundas just west of Ossington. The Baby G is another music venue on Dundas, west of Dufferin. The Garrison is more midsize, with a capacity of about 350. Many local and touring indie bands play there, and this gritty venue proudly declares itself independent and artist-run. Visit for cool indie acts, dance parties, and DJ sets.
The Axis Club, formerly The Mod Club, is another midsize venue in Little Italy. Its capacity is larger than The Garrison at 618 but is great for catching emerging artists. The Axis Club is at Crawford St./College St., just east of Ossington. It hosts acts from all genres and has a club look and feel. The venue was renovated before reopening as The Axis Club with upgrades to the sound and lighting systems.
Near The Axis Club, there is a down-to-earth, spacious (yet cozy) bar called Houndstooth, by College/Ossington. Bands play Wednesdays at 9 p.m., DJs from Thursday-Saturday at 10 p.m., and sometimes karaoke. Check Houndstooth’s monthly calendar on Instagram to see who’s playing.
Also in the heart of Little Italy is Mrs. Robinson, a cool music-centred cocktail bar with a “modern soul food” menu. The bar has a beautiful atmosphere, with stylish decor and an eye-catching wall of audio equipment and vinyl. You can hear soul, funk, disco and hip-hop being spun at Mrs. Robinson, plus live music of a similar feel.
Wiggle Room at Bathurst/Dundas, on Little Italy’s edge, hosts live dance music. It’s also an event planner, record label, and talent roster. Torontonians flock there for house and techno music, and regulars say it’s a nice atmosphere where they feel comfortable.
Finally, mark your calendars for the annual Taste of Little Italy in June and College St. Beats, running June-September. College St. Beats features live music on College for folks to enjoy as they shop, stroll, or enjoy a patio beverage. It’s a lovely way to experience this dynamic, artistic neighbourhood.
This is a taste of the music scene in and around Little Italy’s, which is full of established venues and hidden gems.
