Fall is here, and it’s serving all the cozy vibes - think gorgeous fall colours, pumpkin spice, warm drinks, and of course, the ultimate sweater weather. If you’re on the hunt for the perfect date night to enjoy with your boo this autumn in Downtown Kingston, you’re in luck! I’ve curated a list of fun activities to spice up your season and make some unforgettable memories.

So, message your boo, grab your cutest fit, and get ready to explore all the amazing things Downtown Kingston has to offer this fall!

Feeling the cozy vibes and want to elevate your night in? Swing by The Everly Wine Shop for a great selection of curated wines, artisan cheeses and meats that are perfect for your next chill night at home.

Perfect for planning a cozy date night for two, they’ve got everything you need to create the ultimate wine and cheese board. Cheers to good times and even better bites!

Hop on the Kingston Trolley Tour for their 2-hour Fall Colours Tour. This charming ride takes you through the iconic Fort Henry for spectacular views of the city from atop the hill, up Highway 15 to Kingston Mills, a short stop at Waddell Farms, a cute apple orchard and scenic views through the Village of Sunbury, Kingston Mills, and along the Rideau Canal. Enjoy the stunning fall colours together. 

Level up your date night and treat yourselves to a delicious meal at spots like Black Dog Tavern, Olivea, Tango Nuevo, HEIST, Miss Bao, or AquaTerra. Each place brings its unique flavour and vibe to make your night special.

If you’re craving something a bit more upscale, don’t miss out on The Bank at the Frontenac Club or Le Jardin - they’re absolute must-visits for a romantic evening. 

Ready to keep the vibes going after dinner? Hit up Bar Mayla, The Everly, or Bobbi Pecorino’s Italian Wine Bar for some seriously crafted cocktails and wine. Each spot offers cozy, intimate settings - perfect for winding down and creating that relaxed ambiance.

Whether you’re toasting to the night or just enjoying each other's company, these restaurants have the perfect drinks to elevate your evening! 

Check out Musiikki Café & Whiskey Bar for a great evening of live music! This spot tucked away on Brock Street is known for showcasing local talent in its cute outdoor courtyard that’ll set the mood just right supporting homegrown artists.  

Grab your partner and head on a fun art crawl through Downtown Kingston! Stroll hand in hand as you explore local galleries such as Martello Alley, Gallery Raymond, Martello on Brock, Tri-Art Gallery and more - each stop is a new adventure waiting to be discovered. 

Looking for a laid-back date idea? Start with a stroll down Princess Street. Swing by Balzac’s Coffee and grab a warm drink - maybe a chai latte or some hot apple cider (two of my favourites!) to sip on as you walk.

Then, make your way down to the waterfront and find a spot to chill by the water while watching the sunset. It’s the perfect way to enjoy each other’s company and the beauty of fall! 

Join the Tapas Tour with Kingston Food Tours for a tasty adventure! This guided walking tour takes you on a drool-worthy journey through Downtown Kingston's best small plates, perfect for foodies eager to sample local flavours.

 You’ll enjoy stopping at four restaurants, and trying out a variety of dishes while soaking up all the culinary insights along the way. It’s a fun way to enjoy the season and indulge in Kingston’s finest eats! 

Check out Red House and Kingston Brewing Company - absolute gems in the pub scene for a laid-back date night. With good food, a wholesome ambiance, and plenty of cozy spots for great conversation, these places are perfect for kicking back and enjoying some quality time together. Grab a drink, settle in, and let the good times roll! 

Head over to The Screening Room, Downtown Kingston’s very own independent movie theatre on Princess St, where you can kick back and enjoy a unique lineup of indie films, Hollywood films, timeless classics, and seasonal favourites. Grab some popcorn, snuggle up, and get ready to vibe with each other over some great flicks! 

Ready to get your spooky vibes going? Take the Haunted Walk of Kingston! This outdoor tour takes you through the city’s most haunted spots so get ready for a night of ghostly tales and local legends!  

Wrap up your date night with a delicious fall-inspired gelato from Mio Gelato! Treat yourself to seasonal flavours that capture all the cozy vibes of autumn - think dulce de leche, maple walnut, and more. It’s the sweetest way to celebrate the season together, so grab a scoop (or two) and indulge in a little extra sweetness!