Three Days of Food, Cocktails, Culture and Exploration
Three Days of Food, Cocktails, Culture and Exploration
Just across the river from Detroit, Windsor, Ontario is an easy weekend getaway with more to discover than you might expect. While Iβve crossed the border to Windsor plenty of times before, this three-day visit with Tourism Windsor Essex Pelee Island gave me the chance to slow down and experience more of the city. From Walkerville and Ford City to downtown and the riverfront, the weekend was filled with local restaurants, breweries, cocktail bars, shops, art, history and a few unexpected discoveries along the way.
A Weekend in Windsor at a Glance
Friday: Cross into Windsor β DoubleTree by Hilton β Walkerville Brewery β Funky Chow Kitchen β IKTO Tiki Bar β Gladstone Commons
Saturday: Thyme Kitchen β Canadian Aviation Museum β Ford City & Dropped on Drouillard event β Chapter Two Brewing β OG Pizza β WindsorEats Food Hall β WIFF Alley β TQLA β Maiden Lane β EkΕ
Sunday: The Twisted Apron β Willistead Park β Walkerville shopping β Anchor Coffee β Art Windsor-Essex & Chimczuk Museum β Malden Park
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Driving from Detroit to Windsor & Checking In
I started the weekend by crossing the brand-new Gordie Howe International Bridge, and it was exciting to finally experience it. The bridge itself is beautifully constructed and offers another way to connect Detroit and Windsor, not just by car but also by bike and on foot. When I crossed, the wait was about 15 minutes, and the process was smooth sailing. Of course, youβll want to make sure you have your passport ready before heading across the border.
The Gordie Howe International Bridge isn’t the only option for getting from Detroit to Windsor. The Detroit-Windsor Tunnel is often a quick choice with little wait, while the Ambassador Bridge offers another convenient route between the two cities.
Once I arrived in Windsor, I headed to my home base for the weekend, the DoubleTree by Hilton Windsor Hotel & Suites. Located along the riverfront and close to downtown, it made an easy starting point for exploring Windsor.
Check-in was quick and easy, and of course, I couldn’t head up to my room without grabbing one of those classic DoubleTree chocolate chip cookies first!
But the real surprise was waiting upstairs.
Stepping into my room, the first thing that caught my attention was the view. The Detroit skyline stretched across the river, and seeing the city from this side of the water was such a fun change of perspective. The room was comfortable and had everything I needed for the weekend, including a mini-fridge that would definitely come in handy throughout the trip.
Thereβs more to the hotel than the rooms, too. The second-floor restaurant overlooks the riverfront and Detroit skyline, while the third floor features a state-of-the-art fitness center and an indoor pool with another great view of the city. I didn’t get a chance to experience the restaurant or pool during this visit, but they’re both worth knowing about if you’re looking for a Windsor hotel with riverfront views and extra amenities.
Friday Evening: Exploring Walkerville
After getting settled at the hotel, I grabbed a quick Uber to Walkerville, just about a six-minute drive away. It was the perfect place to begin the weekend, with a neighborhood full of character, restaurants, bars and local businesses all within easy reach.
If you’re looking for things to do in Walkerville, this is the kind of neighborhood where you can easily spend an evening moving from one local spot to the next.
My first stop was Walkerville Brewery, a local craft brewery with deep roots in the neighborhood and a history closely tied to Windsorβs brewing and distilling past. The brewery operates out of one of Hiram Walkerβs original whiskey storage buildings, giving the space a unique connection to Walkervilleβs history. Today, the brewery has a lively atmosphere, especially on Friday nights when live music fills the taproom.
I settled in with a beer flight to sample a few of their offerings, including their award-winning stout. And then there was the pretzel. I had been told it was a must-try, so naturally, I had to order one. One bite immediately took me back to Oktoberfest in Germany. It was that good!
From there, I didn’t have to go far for dinner. Funky Chow Kitchen is right next door, tucked downstairs with stairs leading in from the street. The atmosphere couldn’t have been more different, with colorful, vibrant decor and a playful energy that carries right into the food and drinks.
I tried the Bonsai and River Runner cocktails, along with spicy edamame, sushi rolls and the Lucky Quack, a seared duck breast dish. It was the kind of dinner where I wanted to keep trying a little bit of everything.
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But the night wasn’t over yet.
One of the fun surprises of the evening was discovering that IKTO Tiki Bar is tucked inside Funky Chow Kitchen. The small, intimate space feels like stepping into another world, surrounded by colorful tiki decor. I tried the Mermaid Punch and Scarif Beach, which arrived in a fun presentation that made them almost as entertaining to look at as they were to drink.
From IKTO, I walked a couple of blocks to Gladstone Commons for one final cocktail. I settled in at the bar and tried an off-the-menu drink called the Final Flight, which ended up being the perfect nightcap to a fun Friday evening. I didnβt get a chance to try the food this time, but everything coming out of the kitchen looked and smelled incredible, so Iβll definitely be back to explore more of the menu.
And just like that, four stops into the weekend, I was already getting a pretty good sense of just how much personality Windsor has packed into its neighborhoods.
Saturday: Aviation, Ford City, Local Food & Breweries
Saturday started with breakfast at Thyme Kitchen, where colorful artwork and locally painted pieces fill the space. We ordered the eggs Benedict, which was cooked perfectly, along with the Dubai chocolate waffle. Both were delicious, but the waffle was definitely a standout and a fun way to start a full day of exploring.
The Canadian Aviation Museum was next, and it ended up being one of the most memorable stops of the weekend. I had an amazing tour guide who brought the museumβs history to life, sharing in-depth stories about Windsorβs connection to the war efforts during World War I and World War II, including its role in the British Commonwealth Air Training Plan during World War II.
Seeing the aircraft being restored while learning about the planes, equipment and people behind them made the experience feel much more personal than simply walking through a museum. I even had the chance to get inside one of the jets, which was definitely a highlight.
If you’re interested in aviation, military history or Windsor’s connection to the war efforts, this is definitely a stop worth adding to your Windsor itinerary.
By the afternoon, Ford City was buzzing with energy as Dropped on Drouillard brought vendors, murals, entertainment and drinks into the streets. The one-day annual event gave me a fun introduction to the area, and I even came across a vintage lantern-style decanter that I couldnβt leave without buying.
While Dropped on Drouillard was a special event during my visit, Ford City is worth exploring beyond the event itself. The neighborhood is home to unique shops, local food and drink spots and murals scattered throughout the area. Itβs the kind of place where taking your time and looking around can lead to some unexpected finds.
With the afternoon winding down, I stopped at Chapter Two Brewing, just a short walk away, and settled in with a beer flight. The brewery has a fun patio and also hosts events like euchre nights on select days, adding to its laid-back neighborhood feel. The staff was so friendly and welcoming, making it one of those stops where I immediately felt comfortable settling in and enjoying a beer before moving on.
For anyone looking to check out some of the breweries in Windsor, Chapter Two was an easy addition to the afternoon.
From there, it was time to try one of Windsor’s signature foods: Windsor-style pizza. Original Guys Pizza Pies –Β OG Pizza was a must-try, and it did not disappoint. The story behind the Original Guys goes back to the mid-1980s, when founders Domingos, Sergio and Jason started making pizza together as teenagers at a local restaurant in Kingsville. They eventually turned that early experience into their own pizza business, and today, OG Pizza serves Windsor-style thin-crust pizza made with handcrafted dough, locally sourced Essex County produce and their signature sauce made with locally grown tomatoes. After hearing so much about Windsor-style pizza, I was definitely excited to finally try it for myself.
Next was WindsorEats Food Hall, where the atmosphere is just as much a part of the experience as the food. Part food truck yard and part food hall, the space is colorful, playful and full of personality. Inside, vintage pink couches and chairs mix with picnic tables, while a neon βWe Never Go Out in Styleβ sign stands out against a bright green wall, creating the perfect photo op. Board games are scattered throughout, making it easy to grab a drink, settle in and stay awhile.
Outside, the energy continues with food and dessert trucks, a colorful mural wall and larger-than-life games like Tetris and Guess Who. A DJ was also playing during my visit, adding to the already lively atmosphere.
When it comes to the food and drinks, the lobster rolls are worth trying, and the margarita flights feature rotating flavors throughout the year. Between the music, games, food and drinks, WindsorEats was one of those places where there always seemed to be something happening around me.
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Saturday Evening: Windsor’s Cocktail Bars and Nightlife
As the afternoon turned into evening, the day shifted toward cocktails, nightlife and a little more exploring through Windsorβs streets. I wandered through WIFF Alley, where colorful street art and murals brought even more character to the city. It was one of those spots that made me want to slow down, look around and see what I might find around the next corner.
The evening started at TQLA, a Mexican restaurant with a high-energy atmosphere that immediately brought a different feel to the night. We tried a little bit of everything from the menu, along with a Loco Coco and classic margarita. The loaded fries and La Chica Polo tacos were the standouts for me. With lively surroundings, colorful drinks and plenty of food to share, TQLA was a fun way to kick off the evening.
From there, the night took a more intimate turn at Maiden Lane Wine & Cocktail Bar, an intimate cocktail and wine bar with a low-lit, elegant feel. The menu focuses on wine and specialty cocktails. I opted for the Pigs Can Fly, a cocktail smoked inside a skull before being poured over a large ice cube. The presentation alone was memorable, but the cocktail was just as good as it looked. The friendly staff made the experience even better and gave the evening a more relaxed feel.
The final stop was EkΕ, another intimate cocktail lounge where the atmosphere was right on point. Later in the evening, the upstairs booth came alive with a DJ, bringing more energy to the space while keeping the lounge feel intact. It was a fitting way to end a packed Saturday, with one more taste of Windsorβs nightlife before calling it a night.
Sunday: Walkerville Shopping, Windsor Museums and Riverfront Views
Sunday started with breakfast at The Twisted Apron, and I quickly learned that the recommendation to arrive early was not an exaggeration. I pulled up about 10 minutes before opening, and there were already around 25 people waiting in line. Within minutes of opening, the restaurant was packed. One thing to keep in mind if you’re visiting is that your entire party must be present before being seated.
Was it worth the wait? Absolutely.
If you know me, you know I love a good espresso martini, so finding an entire section of the menu dedicated to different espresso martinis was right up my alley. I also ordered the Crème Brûlée French Toast, and it was every bit as good as it looked. The presentation was beautiful, but the real moment came when I cut into it and the crème brûlée filling melted out. It was absolutely delicious. The eggs Benedict was another standout, cooked and seasoned to perfection.
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After experiencing it for myself, I can definitely see why The Twisted Apron comes so highly recommended. If brunch is part of your Windsor weekend plans, Iβd recommend arriving early, especially on a weekend. It was the perfect way to start my final day in Windsor.
After breakfast, I headed to Willistead Park, and it was the perfect change of pace. The park is a peaceful stretch of greenery with paths surrounding the historic Willistead Manor, giving you a chance to step away from the busier parts of Windsor for a bit.
Built in 1906 for Edward Chandler Walker, the second son of Hiram Walker, the 36-room manor is an impressive centerpiece within the 15-acre park. I didn’t tour the inside during this visit, but walking the grounds gave me plenty of time to take in the architecture, gardens and quiet surroundings before continuing into Walkerville.
From the park, I continued into Walkerville, where the morning turned into a little shopping and plenty of browsing. This was one of those parts of the weekend where I could wander into a shop with no real plan and still walk out having found something I loved.
For shopping in Walkerville, these smaller independent stores were some of my favorite discoveries of the weekend.
At Jones & Co., I found a great selection of unique gifts and pieces that caught my eye. Right next door, Walkerville Mercantile was in the process of moving to a new building during my visit, but there were still plenty of treasures to browse, including men’s clothing and antiques tucked away in the back.
Then there was Walkerville Relics, the kind of antique shop where every time you look around, something else seems to catch your eye. I could have easily spent even more time digging through everything to see what I might uncover.
Rounding out the shopping stops was Urban Art Market, filled with locally crafted gifts ranging from artwork and soaps to shirts and jewelry. Each shop had its own personality, making this part of Walkerville feel less like traditional shopping and more like discovering little pieces of the neighborhood along the way.
After a morning of shopping and browsing, a coffee break at Anchor Coffee was definitely needed. It was the perfect little pause to recharge before continuing on with the day.
With coffee in hand, I continued downtown to Art Windsor-Essex and the Chimczuk Museum, both located in the same building. It was an easy way to experience two very different sides of Windsor in one stop.
If you’re looking for Windsor museums and cultural attractions, this is an especially convenient stop since you can experience both the city’s history and its art scene in one visit.
The Chimczuk Museum takes visitors through the history of the Windsor area, beginning with its geological history and the last Ice Age before moving through Indigenous history, immigration, the Underground Railroad, Prohibition and the city’s connection to the border. There are also interactive exhibits throughout the museum, including a dedicated children’s gallery with hands-on activities, making it a great stop for families.
Next, I explored Art Windsor-Essex, where the focus shifted from Windsorβs history to its creative side. The museum features a mix of historical Canadian, contemporary and Indigenous art, with everything from paintings and mixed media to more thought-provoking contemporary pieces. Each gallery had its own feel, making it easy to wander through and take in something new around every corner.
Before heading home, I made one final stop at Malden Park. From the parking lot, it’s about a 15- to 20-minute uphill walk to reach the top, so comfortable shoes are definitely recommended. The park also has several trails if you want to spend more time hiking and exploring the natural surroundings.
Once you reach the top, the views are worth the walk, with an incredible vantage point of the brand-new Gordie Howe International Bridge. If you’re looking for Windsor views, especially of the bridge and the surrounding area, this is definitely a spot worth adding to your list.
After three days of exploring Windsor from so many different angles, it felt like the perfect place to pause, take in the view and reflect on the weekend.
With one last look at the bridge, it was time to head home. I took the Detroit-Windsor Tunnel back across the river, and the ride was smooth sailing, making for an easy end to a weekend packed with food, cocktails, shopping, art, history and plenty of exploring.
Is Windsor Worth a Weekend Getaway from Detroit?
Absolutely!
While I’ve crossed into Windsor plenty of times before, this trip gave me a completely different perspective on the city. From discovering neighborhoods like Walkerville and Ford City to finding new restaurants, breweries, cocktail lounges, local shops, museums and unexpected little gems along the way, I left with a much better appreciation for just how much there is to experience.
Three days wasn’t nearly enough to see it all, but that’s probably part of the fun. Windsor is close enough for an easy weekend trip from Detroit, yet there is more than enough here to keep you exploring, eating and discovering something new.
If you’re looking for a weekend getaway from Detroit that feels like a change of scenery without going far, Windsor, Ontario is definitely one to put on your list.
A heartfelt thank you to Tourism Windsor Essex Pelee Island and all the incredible local businesses for their warm hospitality and for making this adventure so memorable.
Click here for more highlights from the visit.
Original blog post by Discover With De.
