The Ultimate Tragically Hip Cocktail & Theatre Getaway in Kingston

Looking to escape the hustle of Toronto, Ottawa, or Montreal this weekend? Just down the road, Kingston offers a world away - combining big weekend energy with small-city ease. As the proud hometown of some of Canada's most legendary musical innovators, Kingston is always in tune.

From October 22 – November 8, 2026, the spotlight shines bright on the Kingston Grand Theatre for a spectacular production of the musical It's a Good Life If You Don't Weaken. To help you travel like a local, Kingston’s premier culinary and nightlife hotspots have crafted a curated lineup of Hip-inspired cocktails to power your pre- and post-show celebrations.

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

Start your evening at 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.

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.

Atomica

71 Brock St

• 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.

Black Dog

69 Brock St

• 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.

Dianne’s

195 Ontario St

• 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.

Harper’s Burger Bar

93 Princess St

• 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. Skip the tourist traps and head where the locals go to experience our thriving indie 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, known for hosting fantastic local rock bands.
• The Broom Factory: A relentlessly creative, all-ages innovative hub and music venue that showcases incredible indie talent. 
• Hotel Wolfe Island: Just a short, free scenic ferry ride away, this spot offers a wonderfully distinct, community-centered live music vibe.