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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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Cathedral Church of St. James- Toronto, ON
The Cathedral Church of St. James is home to Toronto's oldest congregation. Established in 1797, the current cathedral is the parish's fourth church constructed on the site.
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Elora Mill Hotel & Spa- Elora, ON
Elora, Ontario is just about the perfect destination for a weekend adventure. Easily explorable on foot, it features outdoor activties, outstanding architecture, and charming hotels. The most well known, Elora Mill Hotel & Spa, is a destination unto itself. Everything at Elora Mill is exceptional.
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Wellington County House of Industry and Refuge- Fergus, ON
Constructed in 1877, this intricate stone Italinate designed by Victor Stewart served as Fergus' poorhouse, a refuge of last resort for the area's indigent. Consisting of mostly unskilled laborers left behind during the shift from agriculture to industry, the complex was initially designed to house 65 residents, who were expected to work to earn their keep. The property later expanded to include a a hospital wing, to accomodate the infirm and elderly.