Located in southern Ontario, nestled along the Detroit River, Windsor is arguably one of the province’s most overlooked and underrated destinations. The area offers a rich history, beautiful waterfront views, award-winning wineries, and a thriving arts scene if you know where to go. There truly is something for everyone.
If you’re looking for a fun getaway only a few short hours from Toronto, look no further. Start planning your new road trip with our list of 17 things to do in Windsor, Ontario.
History of Windsor, Ontario
- Windsor was first settled in 1728, making it the oldest continuous European settlement in Ontario.
- The first settlers established a Jesuit mission near present-day Assumption Church.
- Sandwich Town, the first urban settlement in the area, was established by the British in 1797.
- From the early 1800s until the Emancipation Proclamation and the end of legal slavery, Windsor/Essex played an integral role in the Underground Railroad. The Sandwich First Baptist Church was the first stop in Canada for many slave families fleeing over the border.
- In 1836, a regular ferry service was established, travelling from Detroit to the foot of Ouellette Avenue, leading to the development of present-day Windsor.
- The Hiram Walker and Sons Distillery was established in 1858. In addition to the distillery, a complete company town was established with houses, farms, and stores. This would become Walkerville.
- Windsor was initially called Ford City due to its close ties to the development of Windsor’s Ford Plant. The town was later renamed East Windsor.
- The City of Windsor was formed in 1935 by amalgamating Windsor, Sandwich, Est Windsor, and Walkerville. Riverside, Ojibway, and parts of Sandwich townships would become part of the city in the 1960s.
How to Get to Windsor/Essex, Ontario
For those interested in making the trip from Toronto to Windsor, there are several different transportation options to suit every schedule, budget, and preference.
How far is Windsor from Toronto? The drive will only take approximately 4 hours, depending on traffic if you travel along ON-401 W. However, this route can feel flat and uneventful for those who like driving to enjoy the scenery. Luckily, you can explore many fun places along the way without going far off the highway, including Milton, Guelph, Kitchener, Woodstock, and many more. This is a great way to break up an otherwise monotonous drive.
Whether you don’t have a vehicle or simply want to enjoy your trip without driving, there are several public transit options. If you’re interested in taking the bus, trips from Toronto to Windsor with FlixBus start at just $32 one way. The trip will take just over 6 hours, with stops along the way. You can also travel with VIA Rail starting at $55 one way. This shortens the timeline slightly, with the route taking approximately 4 hours and 15 minutes.
Air travel is the fastest way from point A to point B, but it will come with the highest price tag. Several airlines fly from Toronto to Windsor, with tickets starting at $306 for a round trip.
Best Hotels in Windsor, Ontario
After deciding how you will get to Windsor, Ontario, it’s time to consider where you will stay. There are many options for accommodations in the city of Windsor and throughout Essex County, ranging from modern hotels to unique Airbnb rentals like a wine barrel houseboat floating on the river in the heart of wine country. With so many options, it can quickly feel overwhelming. To help narrow your list, here are 3 of the best hotels in Windsor, Ontario, based on our recent visits to the city:
Caesars Windsor Hotel & Casino
377 Riverside Dr E
Caesar’s Windsor Hotel, connected to the casino, combines luxury and comfort. The rooms offer unique views of the city or the Detroit River, depending on which side of the towers you’re situated. There are two towers – Forum Tower, which is adult-only (19+) and Augustus Tower, which welcomes visitors of all ages. In addition to the convenience of the casino being just steps away, which includes restaurants, shops, and other attractions, the hotel also offers a beautiful adults-only pool.
With so many things to do within the building, you can easily enjoy a weekend without ever needing to leave the casino property. However, if you’re looking for more to do, it’s conveniently located downtown across from the Festival Plaza and just steps from the Windsor Sculpture Park.
Holiday Inn Express Windsor Waterfront
33 Riverside Drive East
Another welcoming Windsor hotel that offers views of the Detroit River from some rooms is the Holiday Inn Express Windsor Waterfront. This hotel is located a short walk from the casino, making it a great option for those planning to see a concert at the casino or exploring the area but searching for more budget-friendly accommodations. Holiday Inn Express Windsor Waterfront offers pet-friendly rooms for those travelling with their furry family members.
Visitors can start their day with the free on-site breakfast. While there are no restaurants within the hotel, its convenient downtown location means you are a short distance from several great restaurants, breweries, bars, and pubs.
Hampton Inn and Suites by Hilton Windsor
1840 Huron Church Road
Located on Huron Church Road, just a stone’s throw from the Ambassador Bridge, Hampton Inn and Suites by Hilton Windsor is an excellent option for those exploring Windsor/Essex as well as those who may be continuing their vacation with a trip into the US. The rooms are light and airy, decorated with a fun pop of colour.
The hotel has a heated indoor pool and hot tub, surrounded by windows to make you feel like you’re outside without worrying about the elements (especially if you’re travelling during the winter months). Visitors are provided with a complimentary hot breakfast. You can access several stores, restaurants, and coffee shops within walking distance. Most popular Windsor attractions, including Windsor’s downtown area, are a short drive (or bus ride) away.
Plan an Epic Road Trip with These 17 Things to Do in Windsor, Ontario (and the Surrounding Area)
Are you ready to start planning your itinerary? Whether you’re a history buff, interested in learning about Windsor’s role in the Underground Railway, or an arts fanatic looking to uncover the talents of local artists, this city has a lot to offer. After visiting the city many times, we have had the opportunity to visit many of the most popular locations while also discovering hidden gems treasured by those who call this city home.
As you create your schedule, check out these festivals, events, and attractions in Windsor, Ontario:
Windsor Sculpture Park
Located along the riverfront, Windsor Sculpture Park is an outdoor gallery that features over 30 large-scale works of contemporary art. The sculptures are installed along the paved walking paths from the Ambassador Bridge and Festival Plaza. As a public park space, the works are free to view. It’s a beautiful way to spend an afternoon checking the unique work of world-renowned artists while enjoying the view of Detroit across the river.
If you want to learn more about the works and the talented artists responsible for creating them, you can view a complete list with details on the City of Windsor website. We highly recommend opening this guide on your phone and taking a self-guided tour, taking the time to read about the artists as you stand in front of their incredible creations.
The Hiram Walker Distillery
2072 Riverside Dr E
An essential part of Windsor’s history, the Hiram Walker & Sons Distillery was founded in 1858. The original distillery was located in the area now known as Walkerville. In fact, Hiram Walker was responsible for creating the distillery and founding the town of Walkerville. He and his family were also involved in the development of many other important locations throughout the area, including:
- Windsor Regional Metropolitan Hospital
- The original Essex Golf Club
- Walkerville Collegiate Institute
- King Edward Elementary School
- Walkerville Technical Institute
- St Mary’s Anglican Church
- The Windsor Airport (formerly Walkerville Airport)
In 1918, Detroit was the first major city in the United States to enforce Prohibition. With Windsor conveniently located across the river, it is estimated that approximately 75% of all illegal liquor that was supplied to Americans during this time passed through the Windsor/Detroit waterways.
As a result of his significant role in Windsor’s history, Hiram Walker was named a person of Canadian National Historic Significance in 1971.
While the distillery once offered tours and tastings, the company has since announced that they would no longer be available. However, they still host events like Whisky Blending Class and other whisky-themed masterclasses. A retail storefront is open to the public on Fridays.
Olde Walkerville Neighbourhood
Originally known as “Walker’s Town,” Walkerville was founded by Hiram Walker in 1890. It began as established homes for Walker’s many workers along with a church and school to support their growing families. Over the years, the town welcomed many different businesses and industries, including becoming an integral part of Windsor’s automotive industry. Ford Motor Company of Canada, Chrysler, and General Motors would all open plants in the town.
Walking through the area today feels like you’re stepping back in time with its many historical homes and buildings. Some historical buildings worth checking out include Willistead Manor (more on that next), St. Mary’s Anglican Church, Tivoli Theatre, the Bank of Montreal Building, and the Barclay Building (formerly Walkerville Town Hall).
Willistead Manor
1899 Niagara St
Built in 1906, Willistead Manor was the home of Hiram Walker’s second son, Edward Chandler Walker. The 36-room mansion was built on a 15-acre estate, creating an unbelievably impressive presence in the historic town. The building was designed by well-respected Detroit architect Albert Kahn and built using gray limestone quarried in the nearby town of Amherstburg, hand-cut on-site specifically for the project.
Edward and his wife, Mary Elizabeth Griffin Walker, only lived in the house for a short time until Edward died in 1915. Mary then deeded the manor to the town of Walkerville in 1921.
Public tours of the mansion are available in July and December each year, with the December tours featuring stunning holiday decorations throughout the property. It is also a popular venue for weddings, receptions, meetings, and other events.
Caesars Windsor Hotel & Casino
377 Riverside Dr E
In addition to a beautiful hotel, Caesar’s Windsor is a great place for a fun getaway. The casino features 85 table games and 1738 slot machines, offering plenty of opportunities to win big. They also host poker tournaments every Friday night and Sunday afternoon.
There is much more to do on-site than just gaming. Browse a selection of luxury boutiques and shops, watch the game at The House Sports Lounge, enjoy live music at one of the casino bars or dance the night away at Ariius Nightclub. When it comes time to eat, there are several different restaurants to choose from, ranging from the high-end menu at Nero’s Steakhouse to a quick bite on the go from Café 377.
One of the biggest reasons to visit is the many concerts at Caesar’s Windsor, which take place in the property’s entertainment venue, The Colosseum. Here, you can enjoy performances from some of the world’s most popular acts and big names. Check the event calendar when you know your travel dates to see if there is a show that catches your attention. Some upcoming performances when writing this include Scotty McCreery, Mariana’s Trench, The Tenors, Blue Rodeo, and Walk off the Earth.
Canadian Aviation Museum
2600 Airport Rd
An interesting Windsor attraction you may not have heard about previously is the Canadian Aviation Museum. The museum is located at the Windsor International Airport, in the original hanger of #7 Elementary Flying Training School, part of the British Commonwealth Air Training Plan. The hanger served as an active training facility from 1940 to 1944.
Here, you can see artifacts and historical aircraft, all displayed in educational exhibits designed to help the public better understand the history of aviation in Canada and globally. They host guided tours, demonstrations, and educational programming. The Wes Bridgen Archive room allows you to read stories directly from British and Canadian veterans over the years.
In addition to their static displays, the museum also maintains a fleet of flyable historic aircraft piloted by volunteer pilots in airshows to reach aviation enthusiasts near and far. You can also book an “Honour Flight” in a de Havilland Canada DHC-1 Chipmunk, Boeing Stearman biplane, or Harvard starting at $99.
Essex Barrels, Bottles and Brews Trail
Windsor/Essex is home to many incredible craft breweries and distilleries, making it a great place for a romantic getaway or a relaxing weekend with your closest friends. While you could simply choose a location and stop by for the afternoon, the Barrels, Bottles, and Brews Trail is a fun option that encourages you to fully experience the region.
This Tourism Windsor Essex Pelee Island program highlights 2 distilleries and 11 craft breweries in Windsor, Ontario and the surrounding Essex County region. This self-guided tour is available as a digital passport or “Flight Log.” After purchasing, the passport can be redeemed for tastings at the participating locations. If you’re visiting for a short time, you can buy a 1-day passport valid for 5 tastings, or, for longer visits, a 7-day option is available, which allows for 9 tastings over a week.
While we have been to and enjoyed every location included on the trail (you really can’t go wrong), one brewery that holds a special place in our hearts is Walkerville Brewery. The first incarnation of this brewery began operation in 1885. While it has had a rollercoaster of highs and lows over the years, including declaring bankruptcy in 2007 and then reopening under new ownership, it has long held a special place in the history of Windsor’s craft beer scene.
Art in the Park
Are you planning a trip to Windsor/Essex in early June? If so, you should definitely add Art in the Park to your itinerary. This popular celebration dedicated to celebrating the talented artists and crafters in the area was first organized by the Art Gallery of Windsor in 1970. Each year since that date, event organizers invite artists, artisans, and art lovers to the stunning grounds of Willistead Manor on the first full weekend in June.
Art in the Park has grown yearly, making it one of Ontario’s largest outdoor arts and crafts shows. Here, you’ll see local works alongside the incredible work of exhibitors from across Ontario and Quebec.
In addition to the wide assortment of artwork and wares on display, the event also includes a food court supported by local high-end restaurants. Refuel with a delicious meal and pair it with a glass of local wine or craft beer. There is also live music and a Kids Zone.
Little Italy District
Via Italy, commonly called Little Italy, is a must-see neighbourhood when you visit Windsor, Ontario. Here, you’ll be met with a unique blend of Italian culture and history, with a variety of shops, cafes, and restaurants, each inspired by the rich Italian heritage of those who built up this area.
Founded in the early 1900s, the neighbourhood was designed to serve as a cultural hub for Italian immigrants and their descendants – allowing them to continue honouring and celebrating their Italian roots. It has inspired the formation of several clubs and associations, each dedicated to supporting and building this community further.
The result is a fantastic destination for an authentic Italian experience within the Windsor city limits. We highly recommend browsing the charming shops and stopping for a bite to eat in one of the many incredible restaurants.
Amherstburg Freedom Museum
277 King St, Amherstburg
As mentioned, the Windsor/Essex area played a vital role in the Underground Railroad and North American black history. The Amherstburg Freedom Museum is a non-profit museum founded in 1975 to share the stories of African Canadians and their contributions to the nation. The property includes the museum itself, the Nazrey African Methodist Episcopal Church, and the Tayor Log Cabin.
It originally operated as the North American Black Historical Museum, but the name was changed to the Amherstburg Freedom Museum in 2015 when the museum celebrated its 40th anniversary.
Visitors can take a guided or self-guided tour through the property and its many educational exhibits. The property also hosts presentations on topics of African Canadian History and the Underground Railroad for school groups, clubs, and community organizations.
Fort Malden National Historic Site
100 Laird Ave S, Amherstburg
The proximity of Windsor/Essex to the US border means the area played an essential role in the War of 1812. Fort Malden served as a stronghold for the British Army in their battle to protect Upper Canada. As the Americans gained traction, the British troops evacuated and burned the fort to the ground in September 1813. It was partially rebuilt and occupied by the American soldiers in 1813-1815 before returning to British control.
In the early 1820s, the British slowly began to rebuild the fort, including brick barracks, a guardhouse, a cookhouse, and an artillery shed. The relationship between the British and the Americans started to improve, but the peace in the area would be broken with the Upper Canadian Rebellion of 1837-38. With the end of the rebellion, any plans for the fort were shelved as soldiers moved on and left the area behind.
The property was acquired by the province of Canada West and repurposed. It opened in 1859 as the Malden Lunatic Asylum, which operated until 1870.
Since then, the property has been used as a lumber yard and planning mill before some parts of the property were subdivided and used for private residences. It was recognized as a National Historic Site in 1921 and now serves as an opportunity to educate people about that time in Canadian history with tours, demonstrations, and museum displays.
Detroit River Ford Fireworks
Arguably one of the most popular things to do in Windsor, Ontario, the Detroit River Ford Fireworks is a spectacle that attracts visitors from across North America. Put on as a collaborative effort by the cities of Windsor and Detroit, this is more than just the normal Windsor fireworks you see on other occasions throughout the year. It has been recognized as one of the largest and most impressive fireworks shows in Canada and the United States.
The firework display features over 10,000 pyrotechnic effects set off from barges on the Detroit River. The show is viewed by thousands of spectators on each side of the river, with both Windsor and Detroit hosting attractions and events along the riverfront. In Windsor, this includes a midway with rides and games, food trucks, local entertainment, and more.
Adventure Bay Family Water Park
401 Pitt St W
If you’re searching for things to do with the kids during your visit, Adventure Bay Family Water Park should be at the top of your list. This indoor water park is a great option regardless of the weather, making it suitable for travel any time of year. The waterpark is conveniently located downtown, just steps away from restaurants and other attractions.
Here, you’ll find 5 waterslides, a surf simulator, a wave pool, and a lazy river. The Splash Zone incorporates a jungle gym and giant water-tipping bucket, creating the perfect opportunity for kids to run and play. For parents travelling with younger kids, the Tot Loch area features smaller-scale slides, a mini water bucket, and other attractions specifically designed for safe play.
Golfing in Windsor/Essex
Windsor/Essex is home to many public and private golf courses, making it the perfect destination for those whose idea of the perfect vacation involves spending the day on the green. The Tourism Windsor Essex Peele Island website’s golf course directory features 21 courses. Some of the more popular courses include:
Whether you’re a seasoned golfer or a beginner looking to learn the game, Windsor’s many golf courses ensure everyone has options!
Point Pelee National Park
1118 Point Pelee Dr, Leamington
Point Pelee National Park may be Canada’s second-smallest national park, but don’t let that fool you. Located just outside Leamington, Ontario, a short drive from Windsor, Point Pelee is the perfect destination for hiking, camping, swimming, birdwatching, canoeing, kayaking, and more. One of the park’s most interesting claims to fame is that the tip of the park is the southernmost point of mainland Canada.
This is a beautiful place to explore, regardless of the time of year. The park offers several different trails, ranging from a casual 0.5 km walk along the Shuster Trail to more adventurous footpaths like the Cactus Field Footpath and West Beach Footpath. There are also 12 km of bike trails.
In the summer, beaches can be found along the length of the peninsula. As temperatures drop, the water becomes too cold for most visitors to be interested in taking a dip, but it creates a stunning view with the ice forming along the rocks.
If you’re interested in exploring the park but didn’t pack all the gear necessary, don’t worry! The park offers several rentals, including bicycles, single kayaks, tandem kayaks, and canoes.
Camp Henry is a collection of 24 oTENTik sites. For those who haven’t seen an oTENTik before, it’s a permanent structure best described as a mix between a prospector tent and an A-frame cabin. Of these, 2 are designated pet-friendly. Each site includes a natural gas BBQ, table, chairs, electrical connections, overhead lights, and heating, making it a great solution even for winter adventures.
Bright Lights Windsor
The perfect way to ring in the holiday season, Bright Lights Windsor is an annual event hosted at Jackson Park. The park glows beautifully, thanks to the thousands of lights and displays that are set up across the property. There are several themed displays, including a Candy Cane Lane, photo-friendly ornaments, and a large central tree that offers a light show set to music throughout the evening.
The organizers have continued adding to the spectacle in recent years, bringing live music and food vendors. Check the schedule for sensory-friendly nights, with changes to the displays to create a softer, calmer environment for those who may otherwise miss out on the holiday magic.
EPIC Wine Country
One of our favourite things to do in Windsor, Ontario, is to join in on one of the many Essex County wine tours, visiting the area’s award-winning wineries and vineyards. While Windsor/Essex may not be the first destination to come to mind when discussing wine, the region has much to offer! Its southern location and weather allow for a longer growing season than most other areas in the province, making producing a broader range of grapes possible.
Whether you’re hoping to take an organized tour or planning your own self-guided tour, you should start with a visit to the EPIC Wine County website. Here, you can purchase a tasting pass for a tasting flight at 6 winery locations or check out upcoming special events at participating Essex County wineries.
Several organizations offer wine tours of the area, but we recommend Grape Vine Tours. They will pick you up anywhere in Windsor or Essex County before taking you for an afternoon of exploring area wineries and breweries. It’s the perfect way to celebrate birthdays or other big events!
Plan Your Windsor/Essex Visit Today
When choosing your next vacation destination, don’t overlook the rich history, vibrant culture, and stunning natural beauty of Windsor/Essex, Ontario. From exploring the historic district of Walkerville to indulging in local wines and craft beers, the city has so much to offer.
Start creating your perfect itinerary with our list of 17 activities and places to visit in Windsor, Ontario – but don’t stop there! There is so much more to offer than we could include in this guide (without making it so long it wouldn’t be readable).
Windsor and Essex County truly offer a unique and unforgettable experience for visitors of all ages and interests. So what are you waiting for? Start planning your next adventure to Windsor today and discover this gem in Southern Ontario for yourself!
