Things to do in Windsor Ontario for a Special Weekend Getaway

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Windsor, Ontario, is a beautiful city full of industry, culture, history, and excitement. It sits across the Detroit River from Detroit and is full of landmarks and entertainment centers. Due to its manufacturing and horticultural heritage, Windsor is known as the Automotive Capital of Canada and the Rose City.

Whether you want to enjoy a day out in the gorgeous Canadian weather or explore different indoor activities like meals, breweries, or other recreation, there is plenty for you to do when you decide to take that special weekend trip to Windsor. Let’s discover what makes Windsor so special and what you can do during your weekend stay.

Windsor Detroit Ambassador Bridge Aerial

Where to Stay in Windsor

Windsor has many different types of accommodation. For a weekend trip, you can book a room at a stunning hotel or keep it simple with a rustic bed and breakfast to get to know the city more intimately. Regardless of where you choose to stay, there are plenty of options to explore based on your price range and where you want to stay while enjoying the city.

Caesars Windsor Casino

Caesars Windsor

Caesars Windsor is a great place to stay for visitors who want to really indulge in the good life. This beautiful hotel attached to the Caesars Windsor Casino is the definition of indulgence, full of comforts and high-end accommodations. The hotel features a bar and lounge, pool, fitness center, free parking, and, of course, direct access to the beautiful Caesars Windsor Casino, where you can play games and watch live entertainment. Rooms tend to cost between $110–$140, depending on the time of year and the number of occupants in the room.

A Hidden Gem B&B

If you are looking for a more homey experience, then A Hidden Gem B&B might be the perfect option for you. Located in Walkerville, a neighborhood of Windsor with great restaurants and shops, this cozy B&B has several rooms with private bathrooms and warm beds. There is also a complimentary breakfast that you can choose from a menu and pick the time you’d like to eat in the morning. The coziness of a B&B helps to make you feel at home and can give you a different experience than a more sterile hotel room.

Inn15 Brewery Loft Suites

This inn comes with an on-site brewery, which is great for guests to love to check out locally brewed beers and craft creations. The Loft Suites are decorated with a modern interior to help create an industrial look, and the Banded Goose Brewing Co. is right downstairs. The location is also in the heart of the Kingsville neighborhood, surrounded by great shops and restaurants to further heighten your experience. The staff are also incredibly helpful in guiding you towards great things to do in the area during your weekend getaway.

Glossy Cherry

Where to Eat in Windsor

Finding a great restaurant in Windsor isn’t hard. In fact, the hard task is trying to narrow down your options for just one weekend! Foodies and regular diners alike will enjoy the wide array of cuisines and different styles of restaurants found by driving around Windsor. From fabulous brunches and breakfasts to high-end dining experiences, there is no shortage of great eateries to explore. You might have to book another weekend getaway just to get to the places you missed the first time.

A Dog’s Breakfast & The Squirrel Cage

These restaurants, owned by the same person and located directly next to each other, are great places for breakfast. These restaurants feature delicious brunches and breakfast options, from eggs benedict to lavender pancakes. The Squirrel Cage is designed to look like a California kitchen with palm trees and west coast decor, while A Dog’s Breakfast takes a more classic approach to breakfast with all-day eats and specialty coffee drinks. You can also try a mimosa or other morning drink as you enjoy your morning meal.


If you didn’t know that Windsor residents love their pizza, then you’ll quickly learn about it at the Spago Italian restaurant. This famous eatery is one of the best pizza places in the city, featuring the unique Windsor take on pizza with shredded pepperoni and special Galati cheese. Spago also offers delicious Italian food and caters to those with special diets with vegan and gluten-free food options. This restaurant is known for its great service and welcoming atmosphere.

The Keg Steakhouse + Bar

If you want to explore a more upscale experience while in Windsor, then The Keg Steakhouse + Bar is a great option. This fine dining restaurant comes with a cost—around $31–$50 a person—but the food is renowned, and the service is spectacular. Located right near the Windsor Riverfront Park, this steakhouse offers a delicious menu full of fancy favorites like escargot, filet mignon, prime rib, and stunning sides. For weekend trippers who want to splurge a little to enjoy the finest food, then The Keg Steakhouse + Bar is a place you can’t miss.

City of Windsor Ontario Sept 2015

Things to Do in Windsor

Windsor has a never-ending list of things to do, so much that there’s no way you can pack it all into a single weekend. However, a few top contenders will interest any visiting tourist and are well worth the stop. These different activities can help you understand more about what makes Windsor unique and how it stands out from other Canadian cities you might have visited.

Walk the Windsor Riverfront

The Windsor Riverfront along the Detroit river is a beautiful stretch of land, featuring stunning views of the river and the Detroit skyline. The riverfront is filled with beautiful waterfront homes, green spaces and parks, and events that take place all year long, like the Poutine Fest and Winter Light Shows. No matter what time of year you visit, you will be amazed at the natural beauty found along the riverfront. You can pick a single garden or park to stay in and picnic at, or walk and drive down the Riverfront to explore the area and take in the sights. It’s a truly one-of-a-kind experience you won’t find anywhere else in Canada.

Traveling Soon? These useful links will help you prepare for your trip.

Explore the Olde Walkerville Neighborhood

The Olde Walkerville Neighborhood is a charming part of Windsor. Once its own township, Walkerville was merged with Windsor in the 1930s and still retains its old charm. The area is filled with walkable streets that border luxury homes and stunning Victorian architecture to delight any tourist. The area is also filled with different restaurants, shops, and even the historic Willistead Manor, which highlights the beauty of the stunning homes of the time. It’s a great place to wander around and explore on your own during a weekend visit.

Get Entranced at the Coventry Gardens

The Coventry Gardens are a carefully cultivated green space located near but not on the Riverfront. Filled with hedges, statues, plants, flowered walkways, and water fountains, this beautiful oasis has some of the most stunning views and topiaries anywhere in Windsor. You can enjoy wandering around in the beautiful gardens, or grab an ice cream and some lunch and have a picnic while watching the Detroit Princess Riverboat float by. Check out the water shows in the fountain or just enjoy the day while out on your weekend trip.

Detroit Princess IMG_8810

Attractions to Enjoy in Windsor

Windsor has amazing attractions and entertainment that are sure to keep you, your traveling partner, or your family busy all weekend long. While the standard theaters and stores are there, you can also explore more unique attractions that make your weekend getaway all the more worthwhile. These attractions are some of the main reasons people choose to visit Windsor, so discover for yourself what makes them so special to visitors and tourists.

Caesars Windsor Casino

The Caesars Windsor Casino is the premier gaming and gambling complex in all of Ontario. This casino has over 80 table games, 2,200 slots, and different tournament series for betting on games and other events. The casino also features live entertainment from top-performing artists, shopping centers and stores, great dining opportunities, and an attached hotel. You could spend your entire vacation at the Caesars Windsor Casino and never get bored. Located right on the Riverfront, the casino also offers spectacular views of the Detroit River and the Detroit skyline.

Pirates of Skeleton Bay Stunt Show 22-09-2011

Adventure Bay Family Water Park

If your weekend getaway includes the kids, then the Adventure Bay Family Water Park is a great place to enjoy time together as a family. The park has over 35,000 square feet of water entertainment, including five giant waterslides, a wave activity pool, a lazy river, a tot splash zone, and a water roller coaster. You can easily spend hours enjoying all of the different spots to play in the water park. It’s a great place to head to in winter and summer, with great climate control and fun activities, no matter what season it is.

Canadian Historical Aircraft Museum

Canadian Aviation Museum

For history buffs who want to explore the history of aviation and plane enthusiasts who want to discover more about their favorite mode of travel, the Canadian Aviation Museum is waiting. The museum is located in the main hangar of the old Elementary Flying Training School at Windsor International Airport. Sights to see include the Avro Lancaster and de Havilland Mosquito restoration projects, along with other displays like the Fleet Fawn, CT-133 Silver Star, Boeing Stearman, and North American Harvard. It’s one of the best air and space museums in Canada, and well worth the visit.

What to Know About Traveling to Windsor

Traveling to Windsor is a fantastic weekend trip, full of different activities and entertainment opportunities. However, there are a few factors to consider before booking your trip. The first is to consider the weather. It can get very cold and snowy in Windsor during the winter, with temperatures between 5 and 20 degrees Fahrenheit. This can limit some of your activities, such as walking around neighborhoods or exploring the waterfront. Keep this in mind as you plan which weekend is best for your trip.

If you are traveling to Windsor from the United States, there are other important factors to consider. Make sure you are measuring your driving speed in kilometers, not miles. Most U.S. cars will have a kilometer meter next to the miles, but know that 50 kilometers is roughly 31 miles and 100 kilometers is around 62 miles. It’s also recommended that you exchange your U.S. dollars for Canadian dollars. While many places will accept U.S. dollars, not every business will. Most banks will help you exchange your money during your trip.

Enjoy Your Weekend Retreat to Windsor, Ontario

Many visiting Ontario may focus on a trip to Toronto, but Windsor shouldn’t be missed either. When looking for a weekend retreat, you often want to explore a city with plenty to do to keep you occupied during your stay and a unique atmosphere and setting that helps you feel as though you have gone someplace new. Windsor provides those things in abundance for visitors looking to get away from it all.

You can explore unique neighborhoods, see stunning sights, and eat delicious food all within walking distance from your hotel. Whether your weekend trip is a one-off visit, or the first of many to come, you can rest assured that you will enjoy every minute of your weekend retreat to Windsor, Ontario.   

Things to do in Windsor Ontario for a Special Weekend Getaway #windsor #ontario #travel #vacation #trip #holiday Things to do in Windsor Ontario for a Special Weekend Getaway #windsor #ontario #travel #vacation #trip #holiday

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Danielle Todorovic

by Danielle Todorovic

Danielle Todorovic has 20 years of extensive experience in a variety of roles within the real estate industry. She is currently the Vice President of Operations at RE/MAX Care Realty.

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