Best of Windsor-Essex, Canada: 10 Places to See, Stay & Sample

Modified: May 21, 2020 | Photos by All photos courtesy of Tourism Windsor Essex Pelee Island

This article was originally published on July 1, 2019 by Raymond Cua of Travelling Foodie.

Just across the Detroit border in Windsor, Canada, you will find a long list of places to explore, along with amazing accommodations, delicious food experiences and libations to satisfy all tastes.

Each year, Tourism Windsor Essex Pelee Island hosts the Best of Windsor Essex Awards where residents & visitors cast their votes online to determine what they deem to be the cream of the crop when it comes to Food and Drink, Shopping, Outdoor Experiences, Entertainment and Accommodations. Here are 10 of the past year’s winners of places to see, stay and sample on your next visit to Windsor.


Point Pelee National Park

Did you know that the Southernmost tip of mainland Canada is at Point Pelee National Park? This Carolinian forest has beautiful beaches, the marsh boardwalk, bird watching, nature trails, and a sign for the 42nd parallel, which also runs through Rome and Barcelona.

The Marsh Boardwalk boasts two towers with panoramic views of the ponds and cattail marsh as well as a 1.4-km walking trail along the floating boardwalk. Point Pelee National Park is a top birding area with over 300 species of birds migrating.

Point Pelee National park boardwalk_650x434


Walkerville has significant historic roots in Windsor.  A former town founded in 1890 by Hiram Walker, owner of Canadian Club Whisky, the Walkerville district is known for its blend of the historic and hip with a multitude of shopping, dining and entertainment options. You will find Anchor Bakery & Espresso Bar, The Twisted Apron, Urban Art Market for original Canadian goods and Timeless Treasures, an antique and vintage store.


Iron Kettle Bed & Breakfast

Owned by husband and wife team, Chef Benjamin Leblanc-Beaudoin and Ginette Tremblay, the 3-acre Iron Kettle Bed and Breakfast is a Feast On certified Bed and Breakfast, meaning all the food served in the B&B uses local and seasonal ingredients from Ontario’s farmers and artisans.  This Victorian home was built in 1867, and it was restored for the bed and breakfast. Now, you’ll find a garden where they grow herbs, a pool and a hot tub. Take a stroll on the grounds and relax in the bright-hued chairs by the pond. Breakfast includes fresh made pastries, fruits, and juices but guests are often treated to a made-to-order omelet feature based on what’s seasonal.

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Caesars Windsor

Experience the beauty, grandeur and luxury of the AAA Four Diamond hotel at Caesars Windsor. Their impeccably appointed guestrooms and suites overlook the manicured waterfront trails and provide city views of both Windsor and Detroit.  Enjoy all that the hotel has to offer during your stay with the in-house spa, delectable restaurants, indoor pool, live entertainment and casino. The Colosseum at Caesars Windsor has a 5,000-seat theatre hosting world-famous concerts.


Pelee Island Winery

Founded in 1979, Pelee Island Winery is the oldest estate winery in Canada with over 750 acres of vineyards in Pelee Island. They are the largest integrated winery in Ontario, complete from farming, harvesting and processing to bottling and retail.

Since Pelee Island Winery has Canada’s most southerly vineyards, its terroir is the most unique compared to all other wineries, making their wines quite special. Being on the southernmost island of Canada, they have an unusually hot and long grape growing season.

Being surrounded by Lake Erie, which is made of limestone bedrock, the soil condition makes it great for pinot noir, making them the largest pinot noir producer in Ontario.

Pelee Island Winery wine glasses_600x363

Wolfhead Distillery & Restaurant

Opened in May 2016, Wolfhead Distillery is the first premium craft distillery in Windsor Essex County offering 3 vodka products and 3 whisky products.

Wolfhead whisky uses 5 year old corn and 13 year old rye aged in American oak bourbon barrels with a 3 degree char inside. Their vodka uses 100% wheat distilled 7 times, making it gluten-free. Wolfhead Distillery also uses limestone filtered water to proof their spirits similar to grey goose and any bourbon whiskey. They have a wide variety of cocktails using their spirits such as the Big Apple Manhattan which uses their Apple Caramel Whisky to add that sweet apple flavor.

Jack’s Gastropub

The Essex region is a primary source for local perch, and, when in the region, you must try the perch at Jack’s Gastropub, a staple in the quaint town of Kingsville since 1898. Owned by Kingsville local Trevor Loop, this farm-to-table restaurant was featured in Food Network Canada’s You Gotta Eat Here in 2013.

Jack’s Gastropub is proudly serves a seasonal menu created with ingredients from local farmers, producers & artisans, along with a local drink list of wine from EPIC wineries, and local brews featuring their in-house Banded Goose Brewing (BgB).

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Armando’s Pizza

If you have not yet discovered Windsor-style pizza then it must be on your list for your next visit!  It’s a thin crust pizza which uses cornmeal under the crust, topped with shredded pepperoni and locally made mozzarella by Galati Cheese Co. The pizza also uses canned mushrooms instead of fresh mushrooms because when Windsor-style pizza began, there were no mushroom farms in Windsor.

Canada’s 2018 and 2019 Pizza Chef of the Year, Dean Litster, makes this award-winning pizza, which has won the Best of Windsor Essex for best pizza every year (to date)! All his pizzas are hand stretched to keep the air in the dough, making it lighter and fluffier than if you were to use a rolling pin.

Armando's Pizza in Windsor_400x600

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Mentioned Attractions And Venues

  1. 1
    Tourism Windsor Essex Pelee Island
    333 Riverside Drive West, Ste. 103, Windsor, ON N9A 7C5
  2. 2
    Point Pelee National Park
    1118 Point Pelee Dr, Leamington, ON N8H 3V4, Canada
  3. 3
    1850 Wyandotte St E, Windsor, ON N8Y 1E3, Canada
  4. 4
    Iron Kettle Bed & Breakfast
    7005 Essex County Rd 46, Comber, ON N0P 1J0, Canada
  5. 5
    Caesars Windsor
    377 Riverside Dr E, Windsor, ON N9A 7H7, Canada
  6. 6
    Pelee Island Winery
    455 Seacliff Dr, Kingsville, ON N9Y 2K5, Canada
  7. 7
    Wolfhead Distillery & Restaurant
    7781 Howard Ave, McGregor, ON N0R 1J0, Canada
  8. 8
    Jack's Gastropub
    31 Division St S, Kingsville, ON N9Y 1P4, Canada
  9. 9
    Armando's Pizza
    3202 Walker Rd, Windsor, ON N8W 3R8, Canada