Windsor Sculpture Park. Photo courtesy of Tourism Windsor, Essex, Pelee Island

Windsor Essex Pelee Island

Mainland Canada’s southern-most destination offers both urban diversity and country charm, with Indigenous, Francophone and Black-Canadian histories contributing to rich cultural experiences. (You can get a leg up on the past via the region’s digital Crossroads Historical Guides.) And it’s a must for appreciators of good food, since a temperate climate plus a long growing season equals farm-to-table delights, which pairs beautifully with a flourishing wine industry.


Willistead Manor. Photo courtesy of Tourism Windsor, Essex, Pelee Island.
Distilling History

Originally its own city, built by whisky tycoon Hiram Walker of Canadian Club fame, today Walkerville is one of Windsor’s most captivating neighbourhoods. Many a distinguished architect contributed to the original “garden city,” for instance Detroit’s famous Albert Kahn, designer of Willistead Manor, a 36-room mansion inside a 15-acre park. (Public tours available seasonally; private tours by booking in advance.)

Historic and hip — no wonder Walkerville was named one of the “coolest neighbourhoods in North America” not long ago. The hip factor means eclectic boutique shopping, with unique enterprises like famed indie book store Biblioasis, printmaking and book arts studio Levigator Press, and the Walkerville Artists Collective, sustaining creative culture through local emerging and established artists.

For a sweet or savoury try The Twisted Apron’s “comfort food with a twist,” cozy Anchor Coffee House, quirky Taloola Café, or the long running Walkerville Brewery.

Downtown Windsor and Sandwich

Chimczuk Museum. Photo courtesy of Tourism Windsor Essex Pelee Island.
Diversity Uncovered

You may know Windsor best for its automotive heritage, but it’s a city with many stories to tell.  Discover Windsor’s Francophone history at Maison François Baby House and its role in the Underground Railroad at the Chimczuk Museum. The museum is also home to the Original People’s Culture and Legacy exhibition, sharing everything from creation stories to Turtle Island history including treaties and residential schools. Youngsters (and fun-loving oldsters) will relish the Chimczuk’s experiential Children’s Gallery and Learning Space.

Upstairs you’ll find Art Windsor-Essex’s visual arts collection — evolving for eighty-some years. The aptly named AWE is known for presenting striking contemporary work (as well as its fabulous skyline views of Detroit).

Windsor's Sculpture Park. Photo courtesy of Tourism Windsor Essex Pelee Island.

Art al fresco is everywhere in Windsor, for instance Artist Alley & Maiden Lane. Formerly a dingy laneway, today its walls are canvasses for some of the big names in street art. Or, head to Windsor Sculpture Park, a veritable outdoor gallery that doubles as a peaceful riverside stroll. Wander in and around striking sculptures by world-renowned artists — some awe-inspiring, some whimsical — some both!

Next stop, Windsor’s Sandwich neighbourhood — former home of pirates, persecuted slaves and the Potawatomi (as well as Odawa and Huron nations). Take the Sandwich Heritage Walking Tour to delve into the backstory of one of Ontario’s oldest settlements. When it comes to interesting walking tours Windsor has no shortage — another of note is Queer Walk, highlighting the history of the city’s 2SLGBTQAI+ community.


The Windsor Eats Food Hall. Photo courtesy of Windsor Eats.
Flavours You'll Want to Follow

Windsor is for food lovers! Take the Follow the Flavours trail to relish the city’s diverse culinary offerings, with potential stops including Spago (Italian); Stelly’s Cuisine & Catering (Jamaican); Zuleeats (Ghanian) and Yemeni Corner Coffee House (Canada’s first Yemeni coffee shop). The WindsorEats Food Hall is an experience unto itself: a food hall and bar featuring food-centric events and festivals. Don’t neglect food for the soul either though — Capitol Theatre Windsor is an historic theatre bringing you film screenings, musicals and concerts. The Capitol is frequented by the Windsor Symphony Orchestra, among other ensembles.


Amherstburg Freedom Museum. Photo courtesy of Tourism Windsor Essex Pelee Island.
Quest for Freedom

Charming Amherstburg, at the mouth of the Detroit River, is steeped in the history of freedom seekers, as it was a busy terminal along the Underground Railroad line. The Amherstburg Freedom Museum is a must to learn more of that history.

It’s also a site that marks Canadian independence from the United States, given its significant role in the War of 1812. Fort Malden National Historic site (open seasonally) was built in 1795 by Great Britain to rebuff potential American invasions. Today the fort’s costumed interpreters and demonstrations of fort life bring the past into your present. And, if you’re curious about the lives of civilians, the Park House Museum shares the heritage of the town and its people.

Caffeine and Co. Photo courtesy of Tourism Windsor Essex Pelee Island.

Then there’s quaint Gibson Gallery, located in a former historic railway station and showcasing the work of Essex County artists. Should you be craving a coffee break, local favourites include Caffeine & Co., Downtown Espresso Café and Flow Café and Bikes.

Epic Wine Route

Travel the Wine Route. Photo courtesy of Tourism Windsor Essex Pelee Island.
The Mediterranean of Canada

An abundance of homegrown fruit and veggies are one reason you can dine so well in Windsor-Essex. One reason you can wine so well is that the Lake Erie North Shore Region is at the same latitude as the Mediterranean — a climate uniquely suited to vineyards. Travel the Epic Wine Route via Route 50, with possible sipping at Vivace Estate WineryDancing Swallows VineyardErie Shore VineyardCREWNorth 42 Degrees Estate Winery & Bistro or Viewpointe Estate Winery. Alternatively, wind through the town of Harrow, taking in Vin WineryMuscedere VineyardsColio Estate Wines, Oxley Estate Winery and Cooper’s Hawk Vineyards. Craving a pint? You’d best have a look at the Barrels Bottles & Brews Trail.


Jack Miner Migratory Bird Sanctuary. Photo courtesy of Tourism Windsor Essex Pelee Island.
Go South

Ontario’s southernmost town boasts Victorian-era architecture, farm-to-table menus and waterfront views. All that and art —  you’ll find local artists’ work at the Carnegie Arts and Visitors Centre. Or no, make that art and birds, given Kingsville’s proximity to the Jack Miner Migratory Bird Sanctuary. Known as “Wild Goose Jack,” Miner is considered by many the father of North American conservationism, and the sanctuary reveals much about his work and about birds themselves, from banding to migration paths.

Green Heart Lunch Club. Photo courtesy of Tourism Windsor Essex Pelee Island.

To experience some of that farm-to-table goodness for yourself consider stopping at local spots including Mettawas StationGreen Heart KitchenEclectic Love or the Pelee Island Winery. The winery also has a location on Pelee Island itself, where you’ll find seven-hundred acres of vineyards and an opportunity to learn all things wine, from growing grapes to making corks. (Not to mention a chance to sample the results of 150 years of winemaking expertise.)


Pointe Pelee. Photo courtesy of Tourism Windsor Essex Pelee Island.
Tomatoes and Tamales

Leamington is the second-largest urban centre in Windsor-Essex, but agriculture is at its heart — it’s  not known as the “Tomato capital of Canada” for nothing. Migrant workers have played a vital role, with one result being a vibrant Mexican-Canadian community, evidenced by the many mouth-watering Mexican restaurants including CancunsitoTaco Tony and the Salsa Caliente Mexican Grill — check the Follow the Flavours Trail for more.

Walk a more literal trail at the Caldwell First Nation Boardwalk, a 10,000 square foot boardwalk overlooking Sturgeon Creek. Wind your way through turtle nesting ponds and monarch gardens, likely accompanied by bird song — the area is famed for winged creatures. Speaking of, a fifteen minute drive from Leamington brings you to Point Pelee National Park, one of the top birding sites in the world.

Experience another side of Leamington at the Leamington Arts Centre, for visual arts exhibitions, cultural programing and an artist’s café and market. (You may also want to dip into The Art Supply Shop to satisfy your own creative leanings.) Theatre buffs note: Leamington is where you’ll find the Bank Theatre, home to the Sun Parlour Players Community Theatre, a beloved local troupe whose history dates back to the 1950s. The Bank itself, which also presents concerts and special events, is located in a yep, you guessed it, former bank, built circa 1850.

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.

Ontario Culture Days thanks Tourism Windsor Essex Pelee Island for their support and assistance with this ON Culture Guide to Toronto Theatre. All editorial decisions were made at the sole discretion of Ontario Culture Days staff.

This guide was written by Li Robbins.