The Ultimate Windsor, Ontario Travel Guide: Where To Eat, Stay, Shop & Explore
Wednesday July 9th, 2025, 6:25pm
The Ultimate Windsor, Ontario Travel Guide: Where to Eat, Stay, Shop & Explore
Original blog by Shana Lee
Windsor, Ontario may sit just across the border from Detroit, but this small Canadian city delivers big when it comes to food, coffee, art, shopping, and hidden gems waiting to be discovered. Whether you’re planning a weekend getaway or looking for a new cross-border adventure, Windsor offers the perfect blend of relaxation, culture, and local charm.
In this complete Windsor travel guide, I’m sharing everything you need to plan your trip — including border crossing tips, where to stay, the best coffee shops, restaurants, breweries, local shopping spots, and unique experiences you won’t want to miss.
Crossing the Canadian Border: What You Need to Know
Crossing the U.S.-Canada border by car is a relatively simple and quick process — especially if you know what to expect.
My Experience:
When we arrived at the border, the process was smooth and straightforward. As we pulled up to the border officer, she noticed that my mom was recording the moment (as moms do), and politely asked that we stop recording — which we did immediately. She then asked a few quick questions: where we were headed, how long we planned to stay, and where we’d be staying during our trip.
That was it. The whole process took about five minutes, and we were on our way to start our Windsor adventure.
Documents You Need:
You’ll need a valid passport or enhanced driver’s license. Double-check expiration dates and keep your ID easily accessible when approaching the border.
What Border Officers May Ask:
Expect questions like: What brings you to Canada? How long will you be staying? Where will you be staying? Keeping your itinerary or hotel booking confirmation handy is helpful.
Check Border Wait Times:
Before heading out, check real-time wait times for the Ambassador Bridge or Windsor-Detroit Tunnel via apps or official websites. Timing your arrival well can help you avoid long lines.
Know What You Can and Cannot Bring:
Cannabis and CBD products are legal in Canada but illegal to bring across the border — even if you’re just visiting. The same goes for certain fresh produce and other restricted goods. When in doubt, leave it at home.
Returning to the U.S.:
The return trip is just as easy. Keep your passport ready, answer a few quick questions, and declare any purchases made during your stay. Also no cell phone use is prohibited while crossing the border to the United States.
Pro Tip:
Be respectful, stay calm, and answer honestly. Border agents are there to do their job, and a friendly attitude goes a long way.
With a little preparation and a flexible attitude, crossing the border can be a quick, easy start to an unforgettable trip.
Upon arriving at A Hidden Gem Bed & Breakfast, I had a feeling I was going to love it — and I was right. As my mom and I walked up to the house, we were greeted at the door by Romeo, the resident cat, who immediately offered belly rubs as a warm welcome. That set the tone for what would be a cozy, peaceful, and memorable stay.
Entry was simple with a keypad and code provided in advance. Shortly after arriving, we were welcomed by Susan and Troy, the lovely couple who run the B&B. They greeted us with open arms and friendly smiles and gave us printed breakfast menus to choose from for each day of our stay — which I absolutely loved. It meant we could tailor our mornings based on how we felt: light and easy or hearty and filling.
Mom and I headed upstairs to our suite, which was thoughtfully arranged with a cozy bed, a sitting area with a couch, a small kitchenette (microwave and mini fridge included), and even a private patio to enjoy a quiet moment outside. The space was clean, comfortable, and inviting — perfect after a long day of exploring.
Every morning began with delicious homemade breakfast, coffee, and warm conversation. We sat at the table with other guests — also a kind, friendly couple — and enjoyed easy chats about Windsor, travel, and life. Susan and Troy gave us some great recommendations for places to visit and added a few insights about the area’s history along the way.
From the warm hospitality to the thoughtful details, A Hidden Gem Bed & Breakfast truly lived up to its name. It felt less like staying at a hotel and more like being welcomed into someone’s beautiful home — and that’s something I’ll never forget.
Located in the heart of Ford City, Chance Coffee is a bright, modern space with serious coffee credentials. They specialize in ethically sourced beans from smallholder farms around the world and keep their menu simple, intentional, and high quality.
I absolutely loved the vibe here — the space had plenty of seating both indoors and out, with lots of natural light and clean, minimal design. I ordered a honey latte that was perfectly balanced and smooth. They also had a tempting pastry selection, and the staff were super welcoming and accommodating. It was the perfect place to kick off my Windsor adventure and settle into the slower pace of the city.
Anchor Coffee House is one of those cozy cafés where you walk in and instantly feel at home. Known for their fresh house-made paninis, soups, and seasonal salads, their menu is full of comforting options made with care.
It was the perfect lunch stop for my mom and me. I ordered the bacon and egg bagel, a fresh harvest salad, and a Brown Sugar Spice Latte that honestly deserves its own fan club. My mom went with the Cuban panini and garden salad, and both dishes were fresh, flavorful, and beautifully prepared. The atmosphere was casual but inviting — the kind of spot you could sit and chat for hours without realizing time has passed.
Harbour House Waterfront Eatery
Located right on the Detroit River with beautiful views of Peche Island, Harbour House offers fresh seafood in a relaxed waterfront setting. We went for dinner and the experience was nothing short of wonderful.
The standout dishes? Their Crab & Lobster Cakes and Coconut Shrimp — absolutely packed with flavor and cooked to perfection. The atmosphere was lively, and the riverfront views added to the charm. If you can, try to catch live entertainment on their spacious patio for the full experience.
Taloola Cafe is part coffee shop, part cozy café — and 100% comfort. It’s the kind of place that feeds both your body and your spirit. Whether you’re dropping in for a cup of tea or sitting down for lunch, the atmosphere is welcoming, artsy, and full of good energy.
We stopped in for lunch and tried the African Ground Nut Stew, the Roberto Panini (salami-prosciutto, asiago cheese, sun-dried tomato spread, fig purée, and spinach on rye), and the Koolbossanova (garlic Polish sausage, sauerkraut dressing, and cheddar on a multigrain bun). Every bite was packed with bold, comforting flavor.
The Loose Goose Restopub & Lounge
The Loose Goose is the kind of place where you go for comfort food and leave full and happy. We tried a bit of everything — the cauliflower tacos, jalapeño cheddar burger, and wings — because vacation is about balance, right?
It was casual, relaxed, and just what we needed after a long day of exploring. Definitely a great spot for a laid-back dinner with hearty portions.
This European-style café is the perfect mix of great coffee, tasty food, and welcoming vibes. My mom and I both ordered sandwiches with chips for lunch, and everything was delicious.
Their summer patio is cozy and full of character — an ideal place to sit, chat, and people-watch. The atmosphere felt easy and unpretentious, like a local favorite you’re glad to have discovered.
This spot surprised me in the best way. Bistro blends Asian fusion flavors with elevated pub classics in a cool, modern space. I ordered the steamed dumplings and Pad Thai, while my mom went for the braised beef short ribs — she said they were fall-off-the-bone tender.
We also sampled a craft beer flight from their rotating list of Ontario beers (over 60 on offer!), and ended with a rich, fluffy slice of Japanese cheesecake. From start to finish, this meal was a standout of the trip.
Let me just say this — Cookie Bar does not play around. These quarter-pound cookies are handcrafted from scratch and packed with flavor.
We paired our cookies with beer (yes, really — and yes, it works), and I’m still thinking about how perfectly gooey and decadent they were. This spot is a must-visit for any dessert lover.
Frost is a small-batch, family-run ice cream shop that takes their flavors seriously — and it shows. Every flavor I tried (and I tried quite a few, strictly for research) was amazing, but the Vietnamese Coffee ice cream? Life-changing.
Made fresh in-house daily with real ingredients, this place is a dream for anyone who appreciates a good scoop. A sweet ending to a sweet day.
Stop 26 is a sweet little neighborhood gem serving up rich, creamy scoops that hit the spot after dinner. We stopped in on our first night and it was the perfect way to end the evening.
I ordered a scoop of espresso and another of coconut praline — both absolutely delicious. What made the visit even sweeter was chatting with Phany, the owner, who was warm, welcoming, and clearly passionate about her shop. It’s the kind of place where you feel like a regular, even on your first visit.
Best Breweries & Distilleries in Windsor
Walkerville Brewery was not only a delicious stop, but also one of the most interesting. Located in the historic Walkerville neighborhood — founded by Hiram Walker of Canadian Club fame — this small-batch brewery combines local heritage with big flavor.
We took a guided tour and learned all about the brewing process and the story behind the neighborhood. It was fascinating to see how much local history is tied to their craft. And of course, we ended with a tasting — my favorite was the Espresso Stout. Rich, bold, and smooth, it was like sipping coffee in beer form (in the best way possible). If you love beer with depth and a good backstory, this place is a must.
Tucked into a beautifully restored historic building, Sandwich Brewing Company serves up craft beers with character. We grabbed seats on the patio and enjoyed the sunshine with a cold Espresso Porter — smooth, roasty, and perfect for a relaxed afternoon. The vibe was chill and friendly, and the space felt like a hidden neighborhood favorite.
Wolfhead Distillery (Amherstburg)
We closed out the trip with a visit to Wolfhead Distillery — and it did not disappoint. Located in nearby Amherstburg, Wolfhead is Essex County’s first premium craft distillery and specializes in small-batch vodka, gin, and whiskey.
The standout for me? The Coffee Whiskey — rich, smooth, and perfectly balanced. It’s one of those spirits that could be sipped neat or mixed into a cocktail (or just added to your coffee, no judgment). The distillery itself has a welcoming, modern vibe with a tasting bar and shop, and it was the perfect final stop before heading home.
Local Shopping & Boutiques
If you love shopping small and supporting local makers, Urban Art Market is a must-visit. This boutique-style gift shop features work from over 30 artists and makers from across Windsor-Essex.
I could’ve spent all afternoon browsing — everything from pottery and jewelry to handmade cards and knitwear was beautifully displayed. There’s so much talent packed into one space, and I left feeling inspired (and with a few goodies, of course). If you’re looking for something truly one-of-a-kind and 100% locally made, this is the place.
Jones & Company is one of those stores that just makes you smile when you walk in. Bright, playful, and full of personality, it’s the perfect spot to pick up a thoughtful gift — or treat yourself.
I found the cutest tote bag covered in plants, and I’m still obsessed with it. From stationery and toys to home decor and accessories, this shop is fun, fresh, and full of charm. Located in the heart of Walkerville, it’s worth popping in even if you didn’t think you needed anything.
Calling all plant lovers — Walkerville Relics is part plant shop, part vintage home goods store, and totally adorable.
What I loved most was how they used vintage vessels as planters, creating displays that felt creative and cozy. It’s the kind of place where you walk in for a succulent and walk out with a new ceramic pot and a story behind it.
Bunch quickly became one of my favorite Windsor finds. It’s warm, welcoming, and full of beautifully curated pieces — from vintage clothing and home decor to candles, vinyl records, and handcrafted goods by local artisans.
I picked up a vintage table runner that they’ll be reworking into a custom tote bag for me — I can’t wait to see the final result! Everything in the shop feels nostalgic yet modern, with a strong sense of creativity and care. Whether you’re into vintage fashion, thoughtful gifts, or good design, Bunch checks all the boxes.
Windsor Sculpture Park (Museum Without Walls)
Walking through the Windsor Sculpture Park felt like visiting an outdoor museum with waterfront views. Located along the Detroit River, this open-air art space features more than 30 large-scale sculptures by artists from around the world.
It was the perfect blend of creativity and calm — art lovers will appreciate the range of styles, and even if you’re just out for a walk, the sculptures add a wonderful sense of discovery to the riverfront trail. We took our time wandering and snapping photos, and I’d recommend it to anyone who wants to experience art outside of traditional walls.
Artist Alley & WIFF Alley (Free 4 Walls Project)
Artist Alley was one of my favorite visual surprises of the trip. This ever-evolving public art project has transformed downtown alleyways into colorful, high-impact galleries. Thanks to the Free 4 Walls initiative, you’ll find murals from internationally known artists like Nychos and Ben Frost tucked between buildings — some pieces stretching two stories high.
You can also explore WIFF Alley, which celebrates the Windsor International Film Festival with film-themed murals and installations. It’s the perfect place to snap a few creative photos and soak up the city’s artsy side.
Chimczuk Museum & Art Windsor-Essex
We spent a full afternoon here and easily could’ve stayed longer. At the Chimczuk Museum, we explored the local history of Windsor, including its Indigenous roots, cultural development, and stories from the area’s past. The exhibits were engaging and interactive, and the Children’s Gallery was full of hands-on fun — great if you’re visiting with little ones.
Next door, Art Windsor-Essex impressed me with its beautiful layout and collection of Canadian, Indigenous, and contemporary art. The space itself is stunning and easy to navigate, and the exhibits sparked some great conversations between me and my mom. This duo of museums is a must-do for culture lovers.
One of the more unique pieces of Windsor’s history is Streetcar No. 351, a beautifully restored 1918 streetcar that once ran along the city’s waterfront.
We visited it early in our trip, and it was such a cool moment to step inside and imagine what public transit looked like over 100 years ago. The streetcar is now a permanent installation, parked near the river, and fully refurbished with original features that transport you right back in time (no pun intended).
It’s a quick stop, but absolutely worth it for a photo and a peek into Windsor’s transportation past — especially if you love hidden gems with historical charm.
This was easily the highlight of my entire trip. At the Canadian Aviation Museum, I had the once-in-a-lifetime chance to take a scenic flight in a vintage Chipmunk airplane — and I’m still not over it. My pilot, Dave, made the experience feel both exciting and completely safe, sharing insights about the aircraft and pointing out sights from above as we soared over Windsor.
Beyond the flight, the museum itself is a gem. It houses beautifully preserved aircraft like Windsor’s own Lancaster bomber and Mosquito KB161. It’s one of those spots that’s just as fascinating for aviation buffs as it is for curious visitors like me.
Outdoor Activities
One day we started our day at Urban Surf, and although I didn’t get out on the water this time, it ended up being one of my favorite stops. I grabbed a fresh fruit smoothie (so refreshing!) and took a peaceful walk around the property, soaking in the sunshine and waterfront views.
The vibe here is laid-back and welcoming — a perfect place to relax or recharge. I loved learning that Urban Surf offers kayak and paddleboard rentals, sunset paddles, and even group fitness classes right on the water. And if you’re looking to tap into your creative side, their Sketch Art Studio is an indoor space where you can sip and explore hands-on art activities at your own pace.
Perfect for a relaxing stroll, Sandpoint Beach Park offers beautiful shoreline views along Lake St. Clair and connects with several walking and biking trails.
Final Thoughts
Windsor, Ontario offers an incredible variety of experiences packed into one charming destination. From its thriving local food scene and vibrant art community to its unique shopping, craft breweries, and museums, Windsor makes for a perfect cross-border getaway.
A special thank you to Tourism Windsor Essex and all of the amazing local partners who made my trip unforgettable. Whether you’re visiting for a quick weekend escape or an extended stay, Windsor offers plenty to discover, enjoy, and explore.
If you’re planning your own trip to Windsor, I hope this guide helps you experience the very best the city has to offer.
Click here and here to see more of this visit to Windsor!
About the Author
Shana Lee is a food and travel blogger based in Toledo, Ohio and the voice behind Shana Was Here. She shares her adventures through the lens of good food, small-town charm, and off-the-beaten-path discoveries — always with her camera in one hand and a snack in the other. Whether she’s exploring international coffee scenes, uncovering local gems, or connecting with communities through storytelling, Shana’s goal is to help you travel deeper and eat better.
Follow along on Instagram @missluvleelocs for real-time travel tips, foodie finds, and behind-the-scenes fun. Want more guides like this one? Visit shanawashere.com for destination inspiration, local love, and a full archive of travel stories.
Sponsored story by Tourism Windsor Essex. For more details on Tourism Windsor Essex click their website, or visit them on Facebook, Twitter, or Instagram.
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