A child interacts with an exhibition at Josiah Henson Museum Photo courtesy of Ontario Heritage Trust

Windsor, Border City

Stretched along the Detroit River, Windsor is a hub of cultural, industrial and creative innovation. The region is speckled with galleries, concert venues, international foods, and – as Canada’s southernmost city and a historic entry point into our nation – rich in Black history.

As a border city, Windsor played an important role in the Underground Railroad, an anti-slavery freedom movement that helped thousands to escape enslavement and start new lives in Canada where slavery had been abolished in 1834. This heritage is preserved in local museums and through annual cultural events.

Day One

Sunny day in the park with bike rider, people sitting on benches Photo courtesy of Tourism Windsor-Essex
Scenic Views and Sculpture

In the morning, start your trip downtown getting to know Windsor’s riverfront, which flows past a variety of landmark experiences. The Detroit River has always been a place of convergence – before settler contact, Indigenous peoples called it Wawiiatanong, meaning ‘where the river bends.”

Whether you travel on foot or pedal along calming bike paths, you must pause to explore the Windsor Sculpture Park. This outdoor gallery holds over 33 works of public art by internationally recognized artists, including Haydn Llewellyn Davies, Sorel Etrog, and Xiaofeng Yin. With waterfront views and paved pathways, this free-entry park can be enjoyed throughout all four seasons.

Man and woman walking towards museum Photo: Ontario Southwest/Chatham-Kent Tourism, courtesy of Ontario Heritage Trust
Josiah Henson Museum of African-Canadian History or Chimczuk Museum
Reclaiming Black History

Discover Black history on a drive to the beautiful village of Dresden about 1.5 hours away. Here you can visit the Josiah Henson Museum of African-Canadian History, an Ontario Heritage Trust stewarded site. Henson was a preacher, author and, while escaping from slavery, a conductor on the Underground Railroad, rescuing 118 enslaved people in his time. Once in Upper Canada, Henson turned his passion for self-reliance and education into a new settlement, Dawn, with a school, farming community and industries. He was fictionalized as Uncle Tom in an anti-slavery novel, Uncle Tom’s Cabin. But this was an identity and name he refuted – so, the museum has recently renamed itself to reflect his objection. The sites of the Dawn settlement and its Underground Railroad stories are now told here through interactive exhibits, Black History Month programming and special events to mark Emancipation Day.

Then visit the nearby Buxton National Historic Site and Museum. Once a settlement for escaped slaves and free Black people, today the site tells the story of the Buxton community and its significance to the Underground Railroad and Black Canadian history. The museum offers guided tours, exhibits, and educational programs that help paint a picture of the community that once lived there.

Another option in Windsor’s downtown core is the Chimczuk Museum, which features a walk-through of Windsor from the pre-historic era to the modern day, including a darkened tunnel-like space which tells the stories of those who traveled the Underground Railroad.

Concert with singers and crowd waving hands Photo Credit Walter C.
The Chrysler Theatre
Stand-up, Singers, and Stage Doors

Return downtown for an evening at the Chrysler Theatre. Situated within the St. Clair College Centre for the Arts, which boasts a competitive musical theatre program, this facility is abuzz with creative talent and offers another stunning waterfront view. There’s something for every audience, including concerts, stand-up comedy, movie nights, drag shows, and professional theatre and dance.

Day Two

Two men holding Canadian Club barrel Photo courtesy of Tourism Windsor-Essex
Rum Runners Bus Tour
Dance the Charleston

Rum and whisky flowed along the Windsor-Detroit border during Prohibition in the 1920s, when spirits and alcohol were outlawed on both sides of the border. For an immersive experience, hop on the Rum Runner’s Tour bus and let a colourful, funny cast of roaring twenties characters take you back in time. Your ticket to this multi-hour tour includes lunch in a reimagined speakeasy filled with piano music of the era and boards to dance the Charleston on, if you’re feeling adventurous and up for a spin.

Framed colourful art Photo courtesy of the Art Windsor-Essex Gallery

Day Three

Man looking at black history art piece Photo courtesy of Tourism Windsor-Essex
Sandwich First Baptist Church
Building Bocks of History

On your final day, dive deeper into Black history around the Windsor area. The first stop is Sandwich First Baptist Church. Sandwich was a town amalgamated into Windsor in 1935, but its history stands tall in this National Historic Site, the oldest – and still active – Black church in Canada. Noted for its simplicity and modest design, the church is built with bricks made of clay dug from the Detroit River. More importantly, the bricks were molded and laid by hand by Underground Railroad refugees, freemen, and runaways who settled in Sandwich. They formed a congregation which further rescued and sheltered more people escaping through the Underground Railroad, often using hidden rooms in the church to shelter newcomers from authorities

Family in National historic site Photo: ©Parks Canada / Fort Malden National Historic Site
Amherstberg Freedom Museum and Fort Malden
Sites to The South

Next stop is small town Amherstburg, 25 minutes south of your morning’s activities. Here you’ll find two museums: for War of 1812 history and re-enactments, go through Fort Malden; for African-Canadian history, spend the afternoon at the Amherstburg Freedom Museum.

Amherstburg was for many the last stop on the Underground Railroad; between 1800 and 1860, 50,000 men, women and children passed through or settled in this sanctuary. Those people would’ve seen the same sites preserved today by the Amherstburg Freedom Museum, like the Nazrey A.M.E. Church and the home of George Taylor, a formerly enslaved man. The museum offers guided and self-guided tours for walk-ins and tour groups, and if you come during certain seasons, you can catch cultural programming like Ribs & Ragtime and Emancipation Celebrations. Curators at the museum put together limited-run exhibits, in addition to a permanent collection of artifacts that educate and inspire.

For lunch, enjoy a picnic in nearby Centennial Park or along the banks of the Amherstburg Harbour.

Couple walks in park on long bridge Photo Courtesy of Destination Ontario
Point Pelee National Park
Eco Exploration

For an unforgettable nature experience, take a scenic drive to Point Pelee National Park, Canada’s most ecologically diverse National Park. Birdwatching here is renowned during the migratory seasons and avid watchers can participate in the Festival of Birds, a 3-day event in May. More than wildlife, the park is also ripe for swimming, canoeing, cycling, or hiking the trails. In the fall, enjoy the annual afternoon arts market, Art at the oTENTiks, or biweekly stargazing nights. The park remains open in the winter, where you can explore quiet trails muffled by snow, surrounded by natural ice formations.

Local Eats

Finish your day by choosing from a selection of well-regarded restaurants in Windsor including Eddy’s Mediterranean Bistro, India 47, Thai Time, or Zuleeats (which promises to take your tastebuds on a trip to Ghana with savoury pies, sausage rolls and butter tarts!).

Want to Take a Detour?
A Black Mecca in Chatham

An hour away from Windsor, and run by the Chatham-Kent Black Historical Society, the Black Mecca Museum is dedicated to uncovering and celebrating the rich history of the region’s Black community. Once known as “The Forks,” Chatham was a sanctuary for runaway slaves and saw a significant increase in its Black population by the mid-1800s. Interactive displays and exhibits explore the lives of Black families who settled there.


Visit the Island

Should you find yourself with additional time to enjoy the region, visiting Pelee Island is a must. This beautiful location houses a rare Carolinian forest, two provincial nature reserves and more than a handful of conservation areas. Wine and history buffs may want to sign up for a Pelee Island Adventures tour of Vin Villa – the most historically significant winery in North America. As part of the tour, you’ll be offered delicious tastings, and the opportunity to wander through ruins and a restored basement that will make you feel as if you’ve travelled back in time.

Your trip at a glance

This guide represents a weekend-long experience, highlighting one of the many wonderful destinations in the area. To suggest a destination for a future guide, please CONTACT US.

All editorial decisions were made at the sole discretion of Ontario Culture Days staff. This guide was written by Li Robbins.