One of The County's most charming hamlets, Waupoos draws its name from the Mississauga First Nation's Chief Waupoos (whose name is derived from the Ojibwe waabooz, meaning "rabbit"). Chief Waupoos' tribe would spend summers on present-day Waupoos Island and then migrate to the valley on the mainland for winter. His trails are still in use today.
During and after the American Revolution Waupoos became a key landing spot and re-settlement zone for Americans that remained loyal to the Crown (the United Empire Loyalists). The area had strategic importance with its views of the Lake and the occasional American warship that considered — but never consummated — an attack.
United Empire Loyalists arriving in Canada.
Once peaceful times took hold the picturesque Conrad David house was built upon a hill top overlooking Lake Ontario. The house is now a historically designated property both for its architectural merit and since our first Prime Minister, Sir John A. MacDonald, once owned it.
The house is now in the hands of the County Cider Company. A fitting situation as today Waupoos is less known for housing ex-Prime Ministers and more famed for the orchards, vineyards and blueberry patches that roll down towards the azure shores of Smith's Bay off of Lake Ontario.
County Cider has reinvigorated the apple industry as it has repurposed the world class apples into an array of world class ciders. Its Waupoos Cider is one of its best known brands as it is available at LCBO's across the province. County Cider offers tastings of all of its ciders and excellent meals at its restaurant, which also has one of The County's best dinning views.
Renovated original barn serves as restaurant and shop for County Cider. Smith's Bay is seen in back. A larger renovated barn is not pictured but is where tastings and cider shopping can be done.
Waupoos is also the place where The County's wineries first took root. Ed Neuser and Rita Kaimin are credited with kicking off what has become an internationally recognized wine industry when they started the Waupoos Winery in 1993. The Winery is the most scenic in The County and allows visitors to sip from their excellent selection of wines while strolling on the dock overlooking the water. The Estate is also home to top notch restaurant that focuses on local ingredients.
Waupoos Winery with tasting bar and shop in the foreground and restaurant behind.