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There’s a distinct historical and agricultural richness about Southern Ontario that’s quite unlike anywhere else. The area was originally settled by several First Nations tribes, including the Iroquois, Huron, Potawatomi, and Odawa, however the French established the first permanent European settlement in the area, Petite Côte (Little Coast), in the mid 18th century. Its proximity to the mighty American (and formerly very British) city of Detroit has lent its fair share of historical facets, too. The area played a role in everything from the Patriot War and the Upper Canada Rebellion and was both endpoint to the American Underground Railroad and a hotbed for rumrunning during American Prohibition.

While the whole area is steeped in history, Windsor, the largest city in the area, is arguably the best place to start diving into the past—and exploring the here-and-now while you’re at it. There are historical homes and museums aplenty if you’re looking to delve into Windsor and Essex County’s background. Or if you’re looking to do a bit more modern exploration, you’d do well to check out some of the art galleries, cafes, microbreweries, farm-to-table-eateries, and boutiques while you’re here. Many reside within Windsor’s historic neighborhoods like Walkerville and Ford City (just to name a few), bringing new life into the old brick buildings and cobbled streets that have been a part of the urban landscape for the better part of a century.

Of course, you’d also do well to explore the great outdoors while you’re in town, too. And the best part? You don’t have to go far. Swathes of greenery speckle the city, many of which have their own historical significance to the area. Perhaps Windsor’s most famous park is the art-adorned waterfront, which allows even the most urban among us to savor the stunning sites provided by the Detroit River—and the city of Detroit itself. It’s also linked to a vast network of trails that crisscross this part of Southern Ontario. These trails link Windsor to the beautiful Essex County and provide a great way to explore this beautiful piece of the country.

That said, you don’t have to stick to the trails to explore Essex County; we’d also encourage a drive! With historic small towns like Essex, Kingsville, and Amherstburg (which is home to the historic Fort Malden) all begging to be explored, you might need to have a motor if you want to see them all. Or, maybe you want to stick to seeing the countryside with your own legs powering your journey. Either way is fine with us. No matter how you explore, though, we’d definitely encourage discovering what these towns have to offer. Aside from the obvious historical charm, there’s also tons of trails, parks, boutiques, shops, restaurants, and historic sites that give Essex County—and the cities within it—its own bespoke character.

One thing you’ll want to check out when you’re out here is the wine (diets and convictions permitting, of course). As the southernmost part of Canada, Southern Ontario’s terroir makes for some spectacular—and distinctly Canadian—vino. Wineries dot the countryside and make for great (and romantic) day trips in and of themselves. And if you’re not as much into wine, the bountiful land has also made for some stellar grains, which means there’s some excellent local beer to be had, too.

Another added bonus of the area’s southern geography is the warm summers and mild winters, which make for some excellent holiday making weather. And seeing how its flanked on three sides by rivers and lakes, you’ll probably want to get out and get in the water—weather permitting, of course. You can rent a standup paddle board, take a kayak trip, or just take the sunbathing route and hole up at one of the many beaches in the area. You may also want to take the ferry out to Pelee Island. Part historic island town, part wine region, and all charming, a day out there is a great way to experience all that Essex County has to offer.

Sound like a lot? Well it is! Windsor and Essex county have tons to offer. Whether you’re in Windsor for a killer concert at Caesar’s, out wining and dining in Essex county, or hopping a bit off the grid on Pelee Island, you’ll have plenty of ways to fill out your calendar. From its historical roots, this part of Southern Ontario has emerged as a charming getaway with a character and charm all its own. From quaint, historic nooks filled with boutiques and breweries to modern architecture brimming with art—and plenty of natural beauty to boot—Windsor and Essex can take you somewhere special—somewhere distinctly WindsorEssex.


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