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Fairmont Château Laurier- Ottawa, ON
I absolutely love train travel, and am all about the idea of a string of grand hotels along railroad routes. While I'm about a century too late to take a Canadian Pacific or Grand Trunk Railway tour (although tourist segments do still exist), many of their stunning Châteauesque hotels still stand, including Ottawa's Fairmont Château Laurier.
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Old Third Vineyard- Hillier, ON
While there are many options for wineries in Prince Edward County, Old Third should be on your short list. Not only do they have a fabulous Pinot Noir and a tasting room housed in a restored century old barn, they have pasta. Really, really good pasta.
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Karlo Estates- Wellington, ON
With over 40 wineries in Prince Edward County, it takes some research to pick the perfect tasting room- or just visit Karlo Estates and spend that time tasting wine.
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Sandbanks Provincial Park- Picton, ON
Sandbanks Provincial Park is home to the largest bay-mouth barrier dune formation in the world. Formed by glaciers 12,500 years ago, sand deposition continues via longshore currents along Lake Ontario's Northern Shore. While wildly popular in the summer, fall brings a more desolate vibe to the windswept terrain, that is all yours to explore.
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Rosemount Inn- Kingston, ON
Thankfully, Kingston, ON has no shortage of historic inns, because it has no shortage of visitors who want to stay in them. While the Rosemount Inn was not my first choice, it turned out to be a beautiful property, in a lovely historic neighborhood, which worked well for our stay.