Some places are forever connected to the artists who shaped them. Kingston is one of those places.
As the hometown of The Tragically Hip, Kingston has long celebrated the band's enduring legacy. From October 22 to November 8, the city invites fans to experience its Forever Hip spirit with It's a Good Life If You Don't Weaken at the Grand Theatre, Hip-inspired cocktails crafted by local restaurants, live music, and the vibrant downtown that continues to inspire visitors and locals alike.
There's no better time to plan a few days in Kingston, where Canadian music, theatre, unforgettable food and drink, and a rich cultural scene come together.
Here is your official roadmap to a weekend of live music, show-stopping theatre, and sophisticated sips.
The Main Event: It’s a Good Life If You Don't Weaken
Plan your stay around the historic Grand Theatre, a cornerstone of Kingston’s culturally vibrant arts community. Catching a performance of It’s a Good Life If You Don't Weaken isn't just a night out - it’s an immersion into local storytelling and creative energy.
It’s a Good Life If You Don’t Weaken immerses audiences in a powerful original story set to the timeless music of The Tragically Hip, capturing the raw energy, heartfelt lyrics, and unmistakable spirit that have become central to Canada’s musical identity.
Locals' Tip: Make sure to book your theatre tickets well in advance, as this highly anticipated musical is the ultimate draw for culture lovers across the region.
Photo credit: Dahlia Katz
Sip the Discography: The Hip Cocktail Crawl
Before the curtains rise or after the final bow, head into the vibrant downtown to taste these creative, themed cocktails.
71 Brock St
Named straight after "Bobcaygeon," the Hip's 1998 single from Phantom Power, one of the most iconic Canadian rock lyrics ever written about small-town Ontario.
- Bobcaygeon Old Fashioned: A deep, rich take on a classic featuring Lot No. 40 dark oak whiskey, Angostura bitters, and smooth maple syrup.
- Dry Bobcaygeon Old Fashioned (0% ABV): All of the sophisticated flavor with none of the proof, crafted with HP Juniper 0% single malt whiskey, Angostura bitters, and maple syrup.
69 Brock St
One of these drinks takes its name from the Hip's 1998 album Phantom Power, which includes "Bobcaygeon" and "Fireworks."
- The Modern Spirit: A bold, complex 2.75oz pour blending El Jimador reposado, Del Maguey mezcal, Tio Pepe fino sherry, Harvey’s bristol cream sherry, Licor 43, cardamom bitters, and a touch of saline.
- Phantom Power (0% ABV): A moodier, non-alcoholic masterpiece made with Oracle 'gin', NOA N/A coffee liqueur, NOA N/A Italian bitter, grapefruit bitters, chocolate bitters, and simple syrup.
195 Ontario St
NOlA Sinking plays on "New Orleans Is Sinking," the Hip's 1989 breakout single. The Silver Suit nods to "Silver Jett" (2002).
- The Silver Suit: A visual stunner that brings the glamour. Sip on NOA 'dry gin', white cranberry, lemon, rosemary, and a dash of festive edible glitter.
- NOLA Sinking: A beautifully textured cocktail featuring Twase whiskey, Luxardo, egg white, and black walnut bitters, served over a striking mango & pineapple King cube and finished with an Amarena cherry garnish.
93 Princess St
Both drinks riff on "Fifty-Mission Cap," the Hip's 1992 track about Bill Barilko, the Leaf's player who vanished in 1951.
- Fifty Mission Smash: Refreshing and vibrant, mixing gin, St. Germain, lemon, house-made blueberry syrup, and fresh mint.
- Mission Zero Smash (0% ABV): A clean-drinking alternative utilizing NOA non-alcoholic gin, elderflower syrup, lemon, blueberry, and mint.
Keep the Music Playing: Where to Catch Live Music
In Kingston, the music doesn't stop when the theatre lights go down. Head where the locals go to experience Kingston's thriving nysuc scene:
- Musiikki Cafe: An intimate, low-lit haven for whiskey lovers and acoustic sessions.
- The Toucan: A classic, high-energy Irish pub tucked into a historic limestone alleyway, where The Tragically Hip got their start in the music scene.
- The Broom Factory: A relentlessly creative, all-ages innovative hub and music venue that showcases incredible indie talent. Entrance is by ticket only, be sure to keep an eye on their current events.
- Hotel Wolfe Island: Just a short, free scenic ferry ride away, this spot offers a wonderfully distinct, community-centered live music vibe.
