Insider’s Guide: Windsor’s Most Iconic Views and Must-Dos

Discovering the Best of Windsor Essex Pelee Island: Iconic Views and Must-Do’s

Original blog by The Cleveland Bucket List

Windsor Essex Pelee Island is a hidden gem in Ontario’s Southwest, offering a blend of nature, art, history, and mouth-watering food. Our journey began with an exploration of Ford City and its vibrant murals, where the colorful art captured the spirit of the community. A visit to the Cookie Bar was the perfect sweet stop; their quarter-pound cookies lived up to the hype, with flavors that left us craving more. We continued our day with a beer tasting at Walkerville Brewery, a local institution that blends history and craft brewing. The brewery’s rustic charm was palpable, and the handcrafted beers offered a perfect taste of Windsor’s brewing culture.

As the sun set, we headed to Mezzo Ristorante for an unforgettable dining experience, where the modern Italian dishes were as artfully presented as they were delicious. We capped off the night with cocktails at Vu Bar at Caesars Windsor, enjoying one of the most iconic views of the Detroit skyline from across the river. The shimmering lights of the city reflected off the water, creating a breathtaking scene that made for the perfect end to the evening.

We kicked off our Saturday with local coffee at Café Amor & Art. Make sure to order the chilaquiles!

Then we set off on our hour drive to venture further into nature at Point Pelee National Park, a must visit destination for anyone exploring the region. Point Pelee is famous for being the southernmost point of mainland Canada, and its natural beauty is simply unparalleled. We walked along the marsh boardwalk, a peaceful trail that winds through the wetlands, where the sights and sounds of nature were all around us. But the highlight was reaching The Tip, where you stand at the edge of the country, surrounded by water on three sides. We walked to the tip and were able to utilize the shuttle to come back. The sense of isolation and tranquility was awe-inspiring.

After soaking in the natural beauty, we satisfied our appetites with Windsor-style pizza at Antonino’s Original Pizza in Leamington. Thin and crispy, this local favorite didn’t disappoint—each bite was bursting with flavor. After lunch, we explored Leamington’s murals and indulged in a wine tasting at Pelee Island Winery, where the award-winning wines were a perfect complement to the picturesque vineyard views. The day continued with a visit to Red Lantern Coffee for the perfect afternoon caffeine fix and The Local Maker, a charming artisan shop in Kingsville, where we discovered locally made treasures. We then headed to the Penalty Box in Windsor, where we enjoyed their famous Chicken Delight, a Windsor staple that lived up to its legendary status. The perfect ending to the day was a peaceful kayak paddle at Urban Surf, which provided a relaxing end to the day.

Our final day started with a delicious breakfast at Anchor Coffee House, a cozy spot with locally roasted coffee and so many amazing pastries and sandwiches. I loved my olive oil cookie! Then, we set off to explore the Windsor Sculpture Park, a stunning outdoor gallery that stretches along the riverfront. We enjoyed a casual walk along the Riverwalk, stopping to admire the large-scale sculptures that dotted the landscape. The juxtaposition of modern art against the natural backdrop of the Detroit River made for an unforgettable experience. We took our time enjoying the views of the Detroit skyline, appreciating the way the city seemed to rise out of the water. Overall, this trip was the perfect weekend getaway from Cleveland, blending art, nature, and local flavors in a way that made Windsor Essex Pelee Island feel both familiar and refreshingly new.

One of the highlights of our trip was our stay at A Hidden Gem Bed and Breakfast. The charming, cozy atmosphere made it the perfect home base for exploring Windsor Essex Pelee Island. Each morning, we enjoyed delightful conversations with the owners, Sue and Troy, over a hearty breakfast. Their warm hospitality made us feel right at home and gave us valuable tips for exploring the area. The B&B’s location in the heart of Walkerville was ideal, with many of the area’s top attractions just a short walk or drive away. Staying here added a personal touch to our weekend and made the experience even more memorable. Each day of this adventure left us with new memories and a deeper appreciation for the unique blend of culture, history, and nature that Windsor Essex Pelee Island has to offer.

Whether you’re paddling at sunset, tasting local wines, or simply taking in the stunning views, this region is full of must-do experiences that will leave you longing to return.

Itinerary Overview:
Friday, September 6th
● 11:30 AM – Leave Cleveland
● 2:30 PM – Check in at A Hidden Gem B&B, 406 Moy Ave, Windsor, ON N9A 2N4, Canada
● 4:00 PM – Ford City Murals + Cookie Bar, 1055 Drouillard Rd, Windsor, ON
● 5:00 PM – Walkerville Brewery, 525 Argyle Rd, Windsor, ON
● 7:00 PM – Dinner at Mezzo Ristorante, 804 Erie St E, Windsor, ON

• After Dinner – Cocktails at Vu Bar, Caesars Windsor

Saturday, September 7th
● 9:00 AM – Breakfast at Café Amor & Art, 1464 Ottawa St, Windsor, ON
● 10:00 AM – Point Pelee National Park, 1118 Point Pelee Dr, Leamington, ON
● 1:00 PM – Lunch at Antonino’s Original Pizza, 270 Erie St S, Leamington, ON
● 2:00 PM – Pelee Island Winery, 455 Seacliff Dr, Kingsville, ON
● 3:30 PM – The Local Maker, 11 Main St E, Kingsville, ON
● 5:00 PM – Dinner at Penalty Box, 2151 Walker Rd, Windsor, ON
● 6:45 PM – Sunset Paddle at Urban Surf, 55 E Pike Creek Rd, Windsor, ON

Sunday, September 8th
● 9:00 AM – Breakfast at Anchor Coffee House, 543 Lincoln Rd, Windsor, ON
● 10:00 AM – Windsor Sculpture Park, Riverwalk

This trip was truly a blend of history, nature, and food culture, hosted by Tourism Windsor Essex Pelee Island, and each stop added a unique layer to our experience in this charming region

Sponsored story by Tourism Windsor Essex. For more details on Tourism Windsor Essex click their website, or visit them on Facebook, Twitter, or Instagram.