Eat, Drink, Sleep and Fun Things to do in Windsor Ontario and Essex County

Good food, better drinks, whiskey history and all of the fun things to do in Windsor Ontario and Essex County

the view of the detroit skyline from windsor ontario holiday inn express waterfront

Windsor Essex County is a hidden gem in Ontario tourism, and I mean that.  The backdrop of the Detroit skyline and the hustle and bustle of a student body from a quality university, suggests that there are many things to do in Windsor Ontario. This is a city and county with much to offer. Historically, the area played a significant role during prohibition and this historical relevance helped create a successful Canadian whiskey industry. Windsor Essex still boasts one of the best known Canadian distilleries as well as some of the foremost wineries in Canada. When considering what to do in Windsor Ontario, let me guide you.

Where is Windsor, Essex, and Pelee Island County?

where is windsor essex county

First things first…where is Windsor? The Windsor Essex and Pelee Island Counties are located in the southern most point of Ontario, across the river from Detroit. It takes roughly three and a half hours to reach Windsor from Toronto. It’s as far west and as far south in Ontario’s tip as you can go. Not a bad drive.

What Was Windsor All About?

view of detroit from the waterfront holiday inn express in windsor one of the best places to stay

I say was because, well, a lot has changed in the area and the foundations of what Windsor was has evolved. During the turn of the century, Windsor played a prominent role in supplying rum and whiskey to the United States in prohibition times. A maze of tunnels running under the city linking Michigan in the United States and Windsor here in Canada indicate the prohibition history deep beneath its roots. The rum-runners were instrumental in creating a market south of the border for Canadian Whiskey supplied by Hiram Walker and his distillery.  Post prohibition, Windsor Essex County relied heavily on the auto industry, with GM at the forefront. With the recent decline of the auto industry in the area, Windsor Essex has once again had to evolve. Tourism is a focus for the region and why not? Having some of the best wineries in the country, a colourful history, and transforming into somewhat of a foodie destination, Windsor Essex Pelee Island Counties are starting to trend and I think Ontario’s South West would agree.

Things to do in Windsor Ontario and Essex County

Where to Stay in Windsor Essex County? 

The Waterfront Holiday Inn Express, Windsor, Ontario

waterfront Holiday inn express windsor ontario

The Waterfront Holiday Inn Express in downtown Windsor provides an incredible view of the Detroit skyline. There is just something special about falling asleep under the picturesque skyline of Detroit. The hotel is ideally situated across the street from the Detroit River, the Dieppe Gardens and the Riverfront Trail. Many of the things to do in Windsor Canada are easily accessible from the hotel, often within walking distance. 

The hotel itself is modern, chic and clean, offering comfortable rooms, great lighting and tons of space for your wardrobe. Rooms have sizeable picture windows providing outstanding panoramic views of both Detroit and the city of Windsor. The breakfast is fantastic, serving plenty of hot and cold items, far better than your average hotel meal. The winning effort however, is the view and the location.

Check out the Waterfront Holiday Inn Express here!

The Grove Hotel, Kingsville Ontario

standing outside the grove hotel in kingsville ontario

The Grove Hotel in Kingsville, Ontario is a unique boutique hotel which really embraces that hipster vibe. Every room in the building is decorated differently, with each focusing on a particular theme or character.  Even the decor in the lobby is unique and quirky, utilizing suitcases for a front desk. At this time of year, an upside down Christmas tree is added for flair. The exterior of the hotel is charming.  It reminds me of a saloon from an old western flick, complete with rocking chairs, yet the inside is as modern as could be. 

My room was called ‘Bye Bye Birdie’ and was obviously…well…bird themed. Decorated with feathered lights, bird walls and even a cat on the bed watching them, the room cleverly alluded to its proposed theme. 

The good vibes of this hotel encourages great camaraderie among its guests. With everyone enjoying the lobby at breakfast with a cup of coffee, the Grove Hotel gives a hostel like feeling with a luxurious twist. The best part, we got a beer sampler to enjoy at the attached micro brewery, another ode to hipsterism. This hotel is great for instagram. 

If you enjoy unique hotels like this, you might enjoy my experience Glamping in Norfolk County, Ontario!

The Iron Kettle Bed & Breakfast, Comber Ontario

iron kettle bed and breakfast in comber ontario

This is a Bed and Breakfast on the right track. The Iron Kettle Bed and Breakfast is owned by a young couple who are making Bed and Breakfasts cool again. Goodbye doily’s and hello pinterest inspiration. 

The Iron Kettle originates in an old 1876 farm house and consists of 5 bedrooms, each with private bathrooms. The B&B features an in ground pool, a hot tub, and an exquisite culinary experience. The owners are fantastic cooks, who use seasonal and local foods in their daily breakfasts, impressing all of their guests. Sometimes staying in bed and breakfasts can feel as if you are intruding into someone’s home. Guests at the Iron Kettle are given a key to the front door so they can come and go as they please on their own schedules. With comfortable sitting areas, beautifully arranged rooms and good vibes only, the Iron Kettle Bed and Breakfast is a cool place to stay.

Check out the Iron Kettle Bed and Breakfast here!

Where to Eat in Windsor Ontario

Spago Italian Restaurant 

antipasto at sago italian restaurant in windsor ontario

Spago is an Italian restaurant that specializes in homemade noodles, and the Italian traditions of  the Casalvieri region. The vibe of the restaurant is based on the meals of an average Italian family. It is big. It is warm, and it is noisy and cheerful. With everyone appearing in jolly spirits, and the smells of wood fired pizza in the background, Spago provides a wonderful dining experience.  

The antipasti appetizer on Spago’s menu featured a large variety of tasty and tangy Italian treats including olives, bruschetta and delicious marinated eggplant. This is an appetizer I’d be happy to share. With the image of pizza shells flying through the air in front of me, it was impossible to not get one of Spago’s traditional wood fired Italian pizzas. I left this restaurant feeling full and pleasant from the delicious foods and great atmosphere.

Taloola Café

outside taloola cafe in windsor ontario

Taloola Café is situated just down the street from one of the best things to do in Windsor Ontario, Willistead Manor. Specializing in organic coffees and teas and a large menu filled with wholesome selections, Taloola café is an excellent stop for a palatable meal, especially breakfast. The decor in Taloola’s Café caters to the traveler and is perfect for the digital nomad, being comfortable, peaceful, and warm.

If you are a coffee lover like myself, then you should check out these 5 best coffee shops to visit in Toronto.

Mettawa’s Station

food and drink at mettawas station restaurant in kingsville ontario

A converted train station, originally commissioned to architect Albert Kahn by Hiram Walker, Mettawa’s is a culinary stop in Windsor Essex County you don’t want to miss. Chef Anthony Delbrocco and his wife Janet opened the train station restaurant in 2008, calling it Mettawa’s in honour of the 1889 Hiram Walker Mettawa Hotel. 

The interior of the restaurant is wood paneled, warm, cozy, and is the perfect place to grab a lovely meal. Chef Anthony’s innovative culinary creations make for a wonderful experience as the food is as good as the history. Mediterranean delights combined with a mixologists drink menu, this cozy restaurant with a colourful history makes Mettawa’s a go to place to eat in Kingsville and Windsor Essex County. 

The Vines Restaurant at Coopers Hawk Vineyards 

coopers hawk vineyards and where to eat in windsor ontario

Coopers Hawk Vineyards is an awesome place to hang out, and its restaurant ‘the Vines’ is a amazing place to eat. What more could you ask for? It is a location which radiates the idea of a winery as a relaxed place to enjoy the company of friends and family while you grab food and enjoy the ambiance and style of a winery. 

The food at ‘the Vines’ was absolutely delicious and perfectly proportioned, plus you know you are going to be able to pair a perfect glass of wine with your meal. The chive and Parmesan fries were a highlight, and the perch was delectable. The restaurant is fresh, open, with enough windows to bring in the daylight and a outside picnic area when weather permits. A must-stop for me.

The Beach House Café

the beach house cafe in kingsville ontario breakfast restaurants

The Beach House Café in Kingsville, Ontario is a restaurant I can get behind. It’s light and airy appearance partnered with its pleasant staff had me wishing this was a restaurant in my own hometown. If so I would go all the time. 

The breakfast we had was top notch. Everything you could want for breakfast was available. Teas and coffees complimented a tasty, filling breakfast. Add background reggae music and a beachy flavour, the Beach House Café experience exceeded expectations. I wished I had the time to go back for lunch. By the way…the lakeside view was not bad either.

Artisans Grill

sophisticated restaurants in windsor ontario

Located in Amherstburg, the Artisans Grill is a cozy and classy restaurant walking distance from the Detroit River. The interior is dark with red luxurious lighting and features. The food is as seductive as the tone of the restaurant. Steak and lobster seemed to be the focus of the menu of this romantic restaurant.  A more perfect place for a glass of wine or cocktail would be hard to find. If you are interested in excellent dining, the Artisans Grill is warm, luxurious, and well located in Windsor Essex County. 

Grove Brewhouse

drinks at the grove brew house in kingsville ontario

The Grove Brewhouse is attached to the Grove Hotel previously discussed. Located in Kingsville, Ontario, it is similar to its hotel counterpart as it is the brew house of a hipster’s dream. Decorated in a modern style, calling out to the millennials of the world, the Grove Brewhouse puts together a selection of unique craft beer brews from their own micro brewery. Delicious snacks and board games can be found in the dining areas as well as a view of the micro brewery itself. A bustling location, the Grove Brewhouse is the perfect setting for a fun night out.

What to do in Windsor Ontario (and Essex/Pelee Island County) 

Visit Willistead Manor

exploring willistead manor one of the best things to do in windsor ontario

Willistead Manor was the home of Edward Chandler Walker, son of Hiram Walker the Windsor whiskey legend and creator of famous Canadian Club Whiskey. Coming from an extremely wealthy background and living in a town named after his family ‘Walkerville’ (now Windsor), Edward Chandler Walker commissioned famous architect Albert Kahn to build a luxurious and grand home for his wife and himself. 

Built from 1904-1906, this Tudor-Jacobean style English Mansion was built with a variety of unique features, such as the fact that it only has one bedroom. Guests were housed in the coach house nearby. After Edward Chandler passed away in 1915. His wife did not wish to live in the large house alone and so she deeded the house to the town of Walkerville and moved out.

inside willistead manor at christmas

In the years following, the house served as the Walkerville Town Hall, the Art Gallery of Windsor and as a public library. The 36 roomed mansion was eventually taken over by preservationists and is now a public park as well as a banquet hall which can be rented for weddings and private parties. During the holiday season, the ‘Friends of Willistead Manor’ decorate the mansion exuberantly, one of the most beautiful Windsor events of Christmas. Private tours can be also arranged.

In the Christmas spirit? The Toronto Christmas Market brings the spirit of Europe to the streets of Canada, check it out!

Take the Ferry to Pelee Island

coopers hawk vineyard in essex county

Pelee Island is the southernmost populated part of Canada. It is located 30 kilometres from Leamington, Ontario and is famous for its vineyards which flourish as a result of the mild climate on the 42 square km island. Pelee Island is also a popular location for those interested in bird watching. 

There are no roads leading to Pelee Island. One must either ferry or fly there. To get to Pelee Island, there are ferries which take between one hour and thirty minutes to two hours leaving regularly from Leamington and Kingsville, Ontario. In the winter season, the Pelee Island Transportation Company operates an air service to the Pelee Island Airport from Windsor. If you are interested in visiting Pelee Island Winery, it is actually located in Kingsville, just the grapes are grown on the actual Island.

Pelee Island Winery

pelee island winery things to do in windsor ontario

Pelee Island Winery is located in Kingsville, Ontario and is one of the most famous wineries in Canada.  As a result of the location and climate of Pelee Island, the growing season is longer than anywhere else in Ontario. The 550 square km vineyard shares the same latitude as fine wine producing regions like Rioja, Spain and Provence, France and benefits from this optimum grape growing climate. Pelee Island produces a variety of high class wines making it the most well renowned of the Essex County wineries. 

A visit to the winery is a must-do when exploring Windsor Essex County.  Sample some wines, enjoy the best wine shopping in Windsor county, and enjoy the experience of visiting one of Canada’s most famous wineries. 

John R. Park Homestead

wreath making class at john r park homestead in essex county ontario

A visit to John R. Park Homestead Conservation Area will have you feeling like you’ve just stepped back in time to the 1850’s. John and Amelia Park’s farm buildings and home have been restored to their 1842 glory, complete with furniture and decor. At John R. Park you can experience baking on the hearth in the kitchen and enjoy constructive craft classes like Wreath Making during the holidays! There is an 1885 steam engine powered sawmill as well as a blacksmith’s shop where the Homestead offers forging classes. Located on the shore of Lake Erie, the John R. Park Homestead is packed with things to do, so make sure you check the event calendar before you visit.

If you are looking to enjoy some fun Christmas activities this season, check out Windsor Essex Pelee Island as one of Ontarios best Christmas getaways! See how I spent my weekend here!

Walk the Detroit River

what to do in windsor ontario walk the detroit river

The Detroit skyline is amazing! It was one of the most surprising parts of my visit and is one of the best things to do in Windsor Ontario.  The Detroit River is lined with parks and green spaces which have a variety of different monuments to check out along the way. A walking and bike path follow the river and lead to some impressive photogenic locations. This would include a narrow pier extending into the Detroit River to facilitate a clear photograph of the Bridge to the United States. Time spent enjoying the cities outdoor space was a top priority of mine.   

Coopers Hawk Vineyards

wine at coopers hawk vineyards in essex county ontario

Coopers Hawk Vineyards is a winery, restaurant, and all around entertaining place to spend some quality time in Windsor Essex County. Not only is the food amazing as mentioned in ‘The Vines’ section above, but the atmosphere of the winery creates a comfortable place to relax and spend the day. With a wonderful green space, families are welcome to stop by the winery to hangout for the day, and for those who over 19 years of age, to enjoy a tasty glass of wine. The winery is open, it’s airy and the pleasant ambiance makes for a relaxed day in an upscale environment. 

Aleksanders Winery 

aleksanders winery in essex county ontario

Aleksanders Winery is located in Leamington Ontario, owned and operated by a Polish couple and their family. Tastings are available in the quaint and sweet store throughout the week as are cheese pairings. Private tours of the winery are also available making this a go to place for Essex County wine tours. A unique experience is brought on by owner Aleks who, as a woodworker and metal fabricator, produced a variety of the tools used to create the delicious wines of Aleksanders Winery. Wife Genny keeps things together. The family dynamic makes this winery a fun place to visit.

Agricultural Tourism is a pretty big deal in Ontario! From Wineries to breweries to lavender farms, check out my experience enjoying agricultural tourism here

Windsor Essex County and Pelee Island is a destination in Ontario with development in tourism beyond my expectations. With so many things to do in Windsor Ontario, including a rich history in prohibition and whiskey, unique architecture, and foodie culture. As well as featuring some of the best wineries in Ontario, the Windsor Essex County and Pelee Island should be on your list of getaway destinations in Ontario.

Disclaimer: I would like to thank team at Windsor Essex and Pelee Island for hosting me as media for the weekend. All of the opinions are my own.

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best things to do in windsor ontario

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