Windsor’s Architectural Gems: Where Every Stop Tells A Story
Thursday June 19th, 2025, 5:02pm
An Unexpected Gem for Historic Home Lovers
Original blog by Phillip Mealer
If you’re based in the Midwest and craving a quick getaway full of character, architecture, and walkable streets, Windsor, Ontario is worth the visit. Just across the river from Detroit, Windsor is an ideal destination for lovers of historic neighborhoods and early 20th-century homes.
What surprised me most about Windsor is how many intact, charming neighborhoods are tucked just beyond the main roads. Walk through Walkerville, a planned company town built in the late 1800s by Hiram Walker (of Canadian Club fame), and you’ll find stately brick homes, Arts and Crafts cottages, and quiet neighborhood streets. Think tree-lined avenues, original leaded glass windows, and a strong sense of place.
Just west, the Olde Sandwich Towne area is one of the oldest European settlements in Ontario. It’s home to some of the region’s earliest structures, including a few that date back to the War of 1812. There’s even a preserved jail and historic pub to stop in for a pint.
One of the best parts about a Windsor visit is how relaxed it feels. There’s less hustle than a big city, but still enough going on — heritage tours, neighborhood cafes, riverside parks, and cozy Airbnbs in heritage homes.
For Midwesterners within driving distance, Windsor offers something rare: a cross-border trip that doesn’t require a long drive or flight, but gives you the joy of discovery, a different currency, and a deep dive into some really lovely old homes.
WHERE TO STAY
Upon arriving in Windsor, I checked into my Airbnb located in Walkerville. I would highly recommend staying in this neighborhood, as it is a close distance to all of the sites and not far from the border, making travel time there and back ideal. The neighborhood was everything you want in an Airbnb location – quiet, beautiful streets, and a friendly atmosphere while being close to all the sites and restaurants.
AFTERNOON ONE
After arriving in Windsor and checking into the Airbnb, I took a walk to Ford City to explore a bit. About a 15 minute walk away, Ford City is rich in history, built around the Ford Motor Company in the early 1900s. Today, it is a revitalized and vibrant community with striking industrial architecture by Albert Kahn and successful businesses, thanks to redevelopment partnerships among businesses and the local and federal government. 36 outdoor murals have been erected on twenty sites along Drouillard Road, honoring and preserving the area’s place in Windsor’s history and that of the global auto industry.
Top spots in Ford City: Chance Coffee, Bunch Retail Store, Cookie Bar, and the murals, of course!
About a 15 minute walk from Ford City, Walkerville Brewery was my next stop to enjoy a flight of beer as a kickoff to my long weekend. This local microbrewery handcrafts both unique and classic beers using quality ingredients infused with the history of their founder, Hiram Walker, the legend who manufactured world famous Canadian Club whiskey. The history of the brewery is evident as you look around the former surge plant that once produced whiskey, now home to some of the finest beer produced in Essex County. In keeping with their roots, some of their beers are even stored and aged in bourbon barrels!
As one of the first breweries in the area during the craft brewery surge, this spot is more than a brewery — it’s a community hub for all people and ages. You can sense the community feel as families with kids, couples, and older adults gathered together to enjoy the atmosphere, and the amazing pretzels, of course.
Fun Fact: Their logo is the first beer trademark in Canada.
What to try: You can’t go wrong with any of the beers here – so many of them are award winners! The cider was also a great choice for those who like a cider but don’t want it to be as sweet. Made with prosecco yeast, this was a great drink for a hot day.
A quick walk from Walkerville Brewery, we ended our day with dinner at Gladstone Commons, a perfect dinner spot with locally sourced, made-from-scratch cuisine. One of the best signs a restaurant is serving high-quality, excellent food is a small menu that frequently changes. You’ll find just that at Gladstone Commons. The restaurant had the perfect ambience for a Friday night dinner, with friendly staff, excellent service, and chic interior. This historic building underwent extensive rehabilitation and renovation a few years back, and the character and history shines through in the restaurant today.
We started with their crispy duck wings, which were phenomenal. For dinner, we ordered the Marinated Chicken Leg and Iberico Pork Secreto. Both meals were above and beyond. They had fun cocktails, like their “famous” cherry margarita, and even non-alcoholic options for those who want to enjoy the fun without the alcohol. Their menu also included classics like the GC Cheeseburger and vegetarian options, making it the ideal dinner spot for all tastes and preferences.
FULL DAY ONE
Explore Amherstburg
For our first full day in Windsor, we took a trip to Amherstburg. Just a 30-minute drive south of Windsor, Amherstburg is one of Ontario’s oldest towns, and it feels like it. With beautifully preserved 19th-century buildings, cobbled sidewalks, and sweeping views of the Detroit River, it’s a perfect stop for historic home lovers. Highlights include Fort Malden National Historic Site, a British stronghold during the War of 1812, and a quiet downtown full of heritage homes, boutique shops, and waterfront cafes. It’s small, walkable, and packed with charm, ideal for a slow afternoon or a half-day trip from Windsor.
Our first stop in Amherstburg was breakfast at Bucket List Coffee Roastery, a small batch coffee roastery and eatery with a great menu for breakfast and lunch. The entire menu is made in-house from scratch, and they roast their own coffee beans shipped in from all over the world. Known for their fresh made cinnamon rolls that bring people from across the county, they offer pastries in addition to their full menu.
I personally love poutine, and I was not disappointed. This is a great spot to start your day or visit any time during your time in Amherstburg for a coffee or sweet treat pick-me-up.
Fort Malden National Historic Site
Visiting Fort Malden offers a vivid step back into early Canadian military history. Located on the banks of the Detroit River in Amherstburg, this former British fort played a key role in the War of 1812 and later housed pensioned soldiers and even a psychiatric asylum. Today, it’s a peaceful, well-kept historic site where you can explore restored buildings, watch musket demonstrations, and walk the grassy ramparts overlooking the river. It’s especially compelling for history buffs, but even casual visitors will appreciate the scenic grounds and sense of connection to Canada’s early frontier days. It was truly a lovely spot to explore and walk along the water, in addition to the history it had to offer.
Armando’s Amherstburg had some of the best pizza I’ve ever had. Their menu features hand-tossed Windsor-style pizza, thin crust pizza and deep dish pizza, with premium Galati cheese, fresh toppings, cured items, and traditional ingredients. I had their signature pepperoni pizza, which was phenomenal. Windsor is known for using shredded pepperonis, and this pizza puts a unique twist on the Windsor classic, featuring 3 pepperoni varieties. They also cater to food sensitivities with gluten-free and vegan options with their own Armando’s 100% Vegan Cheese. Do not miss out on this unassuming pizza shop with next-level flavor!
If you want to keep exploring the city without the walking, Windsor Premier Cruises is a great way to see the sites while sitting down. Enjoy the beautiful waterfront, indulge in an afternoon cocktail or snack, and take in the views of Detroit and Windsor.
If you love barbecue, heaps of delicious sides, and craft cocktails, then Sawyer’s Craft BBQ is your ideal dinner spot. Located in Ford City, this restaurant merges Texas style barbecue with other fun flavors and influences, creating a unique flavor fusion. On top of tender and smoky brisket and ribs, their sides were phenomenal, with an Apple Dill Potato Salad that is the perfect pairing. And for dessert, you can’t skip their Banana Cream Pie.
FULL DAY TWO
Serving comfort food with a twist, The Twisted Apron is the perfect, quaint spot for breakfast in historic Walkerville. In fact, the line was out the door on both Saturday and Sunday morning, so be sure to get there early to secure a table. Their food is never frozen and always prepared with the freshest, Ontario-sourced ingredients, using homemade recipes. Their brunch menu features a full array of both sweet options (like Biscoff Tiramisu French Toast) and savory options (like Chicken N Waffles). For an extra bonus, they also have a lunch menu in case you visit later in the day.
We really enjoyed how fresh and delicious the food was. The homemade jalapeno sauce was perfect, and the fresh berries were a nice touch for a side of fruit. We also tried the Strawberry Shortcake pancakes (featuring strawberry coulis, strawberry crème anglaise, shortcake crumb, whipped mascarpone, and fresh strawberries) and the Dubai French Toast (stuffed with baklava pistachio cream, chocolate ganache, pistachio sauce, pistachio gelato, strawberries, and shredded filo). Both featured homemade ingredients with layers upon layers of flavor.
Step into the elegance of Willistead Manor — a hidden gem nestled in the heart of Walkerville. Built in just two years and completed in 1906, this 36-room mansion was the home of Edward and Anne Walker, a couple brought together by their shared love of art (they actually met while volunteering at an art museum!).
Designed by famed architect Albert Kahn, Willistead Manor blends Tudor-Jacobean revival style with intricate craftsmanship and timeless charm. I especially loved finding all the hidden doors throughout the home and their clear love of architecture and attention to detail. Though the Walkers had no children, their passion for beauty and culture lives on in every corner of the home, from hand-carved woodwork to stained glass details.
Today, it’s not just a house, it’s a living piece of Windsor’s history, open to the public for tours, weddings, and community events. If these walls could talk, they’d tell a story of art, legacy, and a love that shaped a landmark.
Rock Bottom Bar & Grill and Sandwich Brewing Company
Located in historic Sandwich Towne, Rock Bottom Bar & Grill and Sandwich Brewing Company are set in a beautiful old building and boast the area’s largest selection of draft beer. This cozy, family owned and operated restaurant and brewery has a great atmosphere and friendly staff. The patio at Sandwich Brewing Company is perfect for a summer day, and the interior of the brewery is a must-see restoration of a beautiful historic building. The wings are also exceptional.
Explore Sandwich Towne
Sandwich Towne is one of the oldest settlements in Ontario and feels like a hidden pocket of early Canadian history right within Windsor. Founded in 1797, this riverside neighborhood is rich in heritage architecture, from Georgian-era homes to historic churches and even the oldest remaining jail in Ontario. It played a key role in the War of 1812 and the Underground Railroad, and today, its quiet streets, heritage plaques, and cozy pubs make it a fascinating place to wander. For visitors interested in early Canadian and Black history, or just looking to stroll through a neighborhood with real historic texture, Sandwich Towne is a must-see.
Malden Park – Terry Sawchuk Bridge Observation
If you want to enjoy nature, take in the scenery of Windsor, and enjoy a quick hike, visit the Terry Sawchuk Bridge Observation area at Malden Park. Located at the highest elevation point in the Park, the observation area provides a clear vantage of the construction of the Gordie Howe International Bridge – the largest bi-national infrastructure project currently taking place along the Canada-U.S. border. This viewpoint, unveiled in 2023, provides a beautifully framed overlook of bridge construction and river traffic, and was part of community benefit investments tied to the bridge project.
Spago Trattoria is a casual, European-Italian inspired restaurant with a goal to “deliver a true taste of Italy.” The portions were very large, perfect for sharing, and their menu features a wide array of classic Italian dishes. The views were beautiful and the cheesecake was delicious!
Located on Lake St Clair about a 30 minute drive from Walkerville, Urban Surf Co. offers more than paddle boarding and kayaking. This cool community shop is a fun mix of watersports, clay and pottery art classes, summer camp programs, and a smoothie bar. With everything from sunset paddle boarding to live music and sunset bonfires, Urban Surf Co. is a spot the entire family can enjoy.
LAST HALF DAY
For our last breakfast stop, we went to Thyme Kitchen. The menu is chef driven and locally inspired, with gluten-free, vegetarian, and vegan options, as well as a variety of local and organic beverages and a craft cocktail menu. They offer specialty coffee, and the vanilla latte was excellent! It has a fun atmosphere and is a great spot to start your morning.
Legacy Beacon Streetcar No. 351 & Windsor Sculpture Park
Restored by the City of Windsor and now housed at the Legacy Beacon Pavilion, Streetcar No. 351 is a beautifully restored vintage streetcar built in 1918 by the Cincinnati Car Company. It is one of only three surviving examples from Windsor’s extensive electric streetcar network. Originally serving suburban routes to Amherstburg and other riverfront communities until the system’s end in 1939, Street Car No. 351 later became a bait shop and then a private home (it was used as the base of a cottage!) before the city rescued and restored it. In April 2025, Windsor unveiled it at the new Legacy Beacon pavilion on the Detroit River waterfront, where it now offers guided tours and a bilingual exhibition on early public transit, making it a must-see heritage piece for visitors and history buffs alike. Better yet, they even offer snacks and ice cream!
Spanning the Detroit River waterfront, Windsor Sculpture Park showcases over 31 large-scale modern and contemporary sculptures by renowned artists like Elisabeth Frink and Sorel Etrog. You’ll find thought-provoking works such as “Eve’s Apple,” “Tembo”, and “Consophia” — an 18‑ft steel sculpture whose Ojibway title reflects cross-border dialogue. Perfect for a riverside stroll, the park feels like a “museum without walls,” mixing art, nature, and skyline views in one scenic setting.
Mackenzie Hall is a striking mid-19th‑century limestone landmark in Sandwich Towne, originally built in 1855–56 by Alexander Mackenzie, who would later become Canada’s second prime minister, as the Essex County Courthouse and jail. Designed by Albert H. Jordan in a Classical Revival style with Italianate flourishes, the two‑storey building served as a hub for justice until 1963 and later became municipal offices. Saved from decline by local advocates in the early 1980s, it reopened as a vibrant cultural center offering art galleries, theater events, community programming, and guided historic tours. It still retains original features like courtroom benches, an 1860 silent clock, and the old jail cells. Today, Mackenzie Hall anchors heritage walking tours through Sandwich Towne, connecting visitors to the neighborhood’s layered past and its active artistic present.
Some of the coolest design features in Mackenzie Hall include the hand plastered arch by Spring Hurlbut and a unique light fixture that generates light based on sound frequency.
The Perfect Long-Weekend Getaway
Windsor, Ontario is a must visit! If you want a fun trip any time of the year that is full of history and charm while keeping travel woes at bay, consider visiting Windsor. It is a foodie town full of flavor, a rich past, and a vibrant future.
If you want to follow along with my travel journey and join in my love of historic homes, follow me on Instagram – @Occasionally.in.ohio
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