Fall is for day tripping, whether a simple hike, a stroll along the beach or a weekend getaway. Kingston is popular for many reasons: It’s the original capital of Canada, a bit of an up-and-coming foodie hub, it’s the home of Queen’s University where thousands of Torontonians attend each year and so much more.
So, we went, And here are our impressions.
Friday night: Arrival and first impressions
There’s a moment in early October when Kingston feels like it’s been purpose-built for autumn. The limestone buildings glow in the autumn sun.
It’s the season when the Limestone City slows down just enough for visitors to slip comfortably into its rhythm — to savour the food, and history, maybe even take in the colours of the Thousand Islands from the deck of a cruise boat.
With a mix of waterfront scenery, old-world architecture, and a vibrant culinary scene shaped by local farms, Kingston makes for an ideal fall weekend escape. It’s compact and walkable, brimming with historical intrigue and contemporary energy, hidden alleyways and courtyard patios while being close enough to Toronto to make “48 hours in Kingston” feel like a proper getaway without the stress of long travel days.
And, if it’s a weekend to see the kids at uni, it’s also a great guide to those moments when you need to just relax for a few hours.
By the time you roll into Kingston on a Friday evening — whether by train, bus, or a scenic two-and-a-half-hour drive from Toronto — the city has already begun to glow. The limestone façades, the waters of Lake Ontario rippling in the sunset. Students from Queen’s spill out of cafés, locals stroll the streets, and the faint sound of live music drifts from pubs and bars.
There are a number of centrally located hotels, including the Kingston Marriott, which offers fantastic views and spacious accommodations including some with balconies with water views.
There are also plenty of smaller inns and hotels downtown offering heritage charm and walkable access to everything worth seeing.
Friday night dinner: Farm-to-Table, Kingston Style
Fall is harvest season here, and Kingston’s chefs take it seriously. The city’s restaurants draw on the bounty of local farms from Prince Edward County and the Rideau corridor — expect menus rich with squash, root vegetables, and Ontario cheeses.
The Kingston food and restaurant scene really took off, according to local lore, with the establishment of Chez Piggy, founded by former musician Zal Yanovsky of The Lovin’ Spoonful, which serves hearty fall fare in a rustic former stone stable.
Fun fact: There are also more restaurants per capita in Kingston than any other city in Canada.
One great way to get the lay of the land is on a food tour, which can include some fantastic local spots such as Dianne’s. A restaurant that boasts the unlikely fusion of East Coast and Mexican cuisines. But, it works and it’s a charmer.
Other spots worth noting from our tour include Olivea for delish Italian, and Atomica Kitchen for amazing pizza and delish craft beers in a very lively fun atmosphere.
A great option for dinner is The Everly Restaurant & Lounge just a couple of blocks from the Marriott at 171 Wellington St. Owned and operated by local hospitality vets Amber Thom and Jamie Hodges, The Everly offers a rotating menu of refined yet approachable classic dishes crafted from fresh, local ingredients. We found the service to be top-notch with food to match, while the stylish room was bustling with activity.
Saturday morning: Coffee, markets and old stones.
Wake early — Kingston mornings in October are crisp and quietly beautiful. Step out into the chill and follow the smell of baking bread to Pan Chancho Bakery & Café, the local institution for buttery croissants, house-made granola, and dark roast coffee. .
From there, stroll to Springer Market Square, home to the Kingston Public Market, the oldest continually operating market in Ontario. On fall weekends, it bursts with seasonal colour: baskets of apples, maple syrup, honey, late-harvest vegetables, and local flowers. Chat with farmers, taste fresh cider, and pick up a snack for later — maybe an apple fritter or a wedge of aged cheddar from a nearby producer.
The market sits in the shadow of Kingston City Hall, a gorgeous domed building that feels more like a state building than a municipal office — fitting, since this limestone charmer was actually Canada’s capital in the 1840s before moving up river to Ottawa. Take a few minutes to wander the square and admire the architecture, then follow Ontario Street toward the lake.
Saturday afternoon: Bike rides, waterfront history
Kingston’s waterfront tells its story better than any museum — though there are plenty of those, too. Start at the PumpHouse Steam Museum, a beautifully preserved 19th-century waterworks building where massive steam engines once powered the city’s pumps. There is always something interesting going on at this revamped facility.
Walk south about 20 paces and rent a bicycle at Ahoy Rentals, and hit the waterfront trail, which breezes past some fantastic parkland, the southern edge of Queen’s University and the now iconic Gord Downie Memorial Pier.
Next stop is the Tett Centre For Creativity & Learning, a city-run arts centre that sits on Lake Ontario. Stop by the little gallery inside the arts centre then sashay down the corridor to the Juniper Café, an absolute stunner on the shore of Lake Ontario. Wonderful coffee and snacks.
Then make your way to the Kingston Penitentiary Museum, just up the road from the now-decommissioned Kingston Penitentiary itself. Tours of the penitentiary, led by former corrections officers, are both haunting and fascinating. Then head for home.
Saturday Night: Music and More
As the light begins to fade, make your way up to Fort Henry, the city’s crown jewel of history and high ground. The 19th-century limestone fortress, built to defend the harbour and the Rideau Canal entrance, looks particularly atmospheric at dusk.
From here, the view of downtown Kingston is unforgettable: the gold dome of City Hall glimmering above a patchwork of rooftops, the lake catching the last light, and the silhouettes of islands fading into mist.
It’s also a perfect time to explore the city’s hidden alleyways, former carriage roads that wind through the downtown core.
For dinner, tuck into the bustling and fun Black Dog Tavern, a classic brasserie in the best possible way with delish cocktails and fantastic fare from massive delicious salads to French pub classics and even some very delicious pasta.
Time for some music, one of the things Kingston does very well from big concerts and carefully curated shows at the Isabel Bader Centre for the Performing Arts. Some of the best shows in town will happen at smaller venues whether a pub for an Irish session or a bar such as the Toucan or Musiikki Cafe there is always something happening in downtown Kingston.
Sunday morning: campus, culture and coffee
Start your second morning at De Mello Coffee, an easy and breezy café with delicious coffee.
Take the morning to stroll through Queen’s University campus, where Gothic Revival architecture, ancient trees, and the clang of bike bells will put a smile on your face. Don’t miss the Agnes Etherington Art Centre, a small but impressive gallery featuring Canadian, Indigenous, and European works — including pieces by Rembrandt and Emily Carr.
Sunday Afternoon: Thousand Islands Cruise
No visit to Kingston in the fall is complete without a Thousand Islands boat tour. This scattered array of more than 1,800 islands stretching along the St. Lawrence River, is legendary for its beauty — and in autumn, it’s nothing short of magical. Trees flame with reds and golds, the water mirrors the sky, and historic cottages peek out from between fiery maples.
Book a cruise with Kingston 1000 Island Cruises on the Island Queen departing from the downtown dock. Opt for a three-hour tour that includes lunch, surprisingly delicious, and narration about the region’s shipwrecks, smugglers, and summer estates, and step out on deck for the full sensory hit: cool wind, the smell of leaves and woodsmoke, and that glittering water shifting from teal to bronze under the October sun.
Cap off the afternoon with a walk along the waterfront then grab a pint at the cheery Kingston Brewing Company or a glass of red at Tango Nuevo.
If you have extra time
- Wolfe Island: Take the free ferry across the channel for a peaceful bike ride among fall fields and a stop at the wind farm lookout.
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Prince Edward County: Just an hour west, this wine region offers golden vineyards, farm stands, and tasting rooms at their autumn best.
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Frontenac Provincial Park: Hike through granite ridges and maple forests just north of the city — a photographer’s dream in October.
