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Toronto, Canada
Start your trip exploring Kensington Market and the Distillery District for great food and local vibes. Don't miss the waterfront trail along Lake Ontario for an easy urban hike. Stock up on supplies at St. Lawrence Market before hitting the road.
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Niagara-on-the-Lake, Canada
This charming town is the heart of Ontario's wine country with dozens of world-class wineries like Peller Estates and Inniskillin. Walk or cycle the Niagara River Recreation Trail along the stunning gorge. Don't miss a boat tour to get up close to Niagara Falls just 20 minutes away.
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Cherry Valley, Canada
Known as 'The County', this island destination is packed with boutique wineries, farm-to-table restaurants, and sandy beaches at Sandbanks Provincial Park. Hike or bike the quiet country roads between vineyards and lakeside stops. Take a kayak or boat tour on the Bay of Quinte for a perfect on-the-water afternoon.
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Kingston, Canada
Kingston sits where Lake Ontario meets the St. Lawrence River and the Rideau Canal — ideal for a scenic boat cruise through the Thousand Islands. Explore historic downtown, Fort Henry National Historic Site, and the vibrant local food scene. The waterfront is walkable and lined with great spots for fresh local fish.
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Gananoque, Canada
Canada's most iconic provincial park offers incredible hiking, canoe tripping, and wildlife watching including moose and loons. Paddle the Canoe Lake or tackle the Centennial Ridges Trail for sweeping views over the boreal landscape. Stop at the Algonquin Logging Museum and grab a meal in the nearby town of Huntsville.
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Huntsville, Canada
Collingwood sits on the southern shores of Georgian Bay with great hiking along the Niagara Escarpment and the famous Bruce Trail. Take a scenic boat cruise on Georgian Bay or kayak around the rocky shoreline. The downtown strip has excellent farm-to-table dining and local craft breweries worth lingering over.
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Gravenhurst, Canada
Return to Toronto for a final night to celebrate the end of your loop. Head to the Harbourfront for a sunset stroll or grab a rooftop dinner in King West. It's about 150 km from Collingwood — an easy, scenic drive back through the countryside.
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Toronto, Canada