The Ultimate 3-Day Windsor & Essex County Getaway
Did you know that one of the best vacation destinations in the region is less than 30 minutes away from Detroit? Whether you are visiting from Metro Detroit or live on the outskirts of Essex County, taking time to explore this vibrant area is a fantastic way to support local businesses and discover incredible hidden gems. This past weekend, I took part in a jam-packed three-day adventure filled with delicious bites, exciting events, and scenic stops. If you are looking to plan a similar staycation or quick trip across the border, here is your ultimate itinerary!
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Day 1: Walkerville, Urban Surf Co. & Downtown Nightlife
Getting Here & Checking In
If you are traveling from the U.S., driving across the border via either the Detroit–Windsor Tunnel, Gordie Howe International Bridge (cheapest option), or the Ambassador Bridge makes for a quick and seamless start to your trip. Upon arriving in Windsor, check in at the Four Points by Sheraton Windsor Downtown. Centrally located, it provides easy access to key attractions, comfortable accommodations, and hassle-free parking.
Lunch & Sweet Treats in Walkerville
Kick off your afternoon in Walkerville, a charming, artsy neighborhood located just east of the downtown:
- The Grand Cantina: Enjoy a vibrant Tex-Mex lunch paired with exceptional margaritas.
- The Cookie Bar: Stop by right after for a fresh, delicious dessert. Their chocolate chip cookie is so good but they routinely swap out flavors based on the season!
Outdoor Adventure at Urban Surf Co.
Next, gear up for an outdoor excursion with Urban Surf Co. I was able to do stand-up paddleboarding through the canals and along the river! It offers a scenic perspective of the shores and local nature. If paddleboarding is not your speed, they also offer pottery classes, cold plunge experiences, and wellness sessions.
Dinner, Entertainment & Nightcap
For dinner, head to The Loose Goose in Downtown Windsor. Famous for offering 50+ wing flavors, it is an essential local stop. Its central location makes it easy to walk to evening entertainment, such as catching a show at Caesars Windsor.
Wrap up your evening with a relaxing stroll along the waterfront and through WIFF Alley, which features impressive artwork celebrating iconic films. Finally, cap off Day 1 with a craft cocktail or glass of wine at Maiden Lane Wine & Cocktail Bar, located steps away from your hotel.
Day 2: Coastal Parks, Local Gems & Essex County Wine Trail
Morning Exploration in Essex County
Day 2 you will go south into beautiful Essex County. Start with breakfast at The King St Cafe, then spend your morning exploring Holiday Beach Conservation Area. Located on the southern edge of Essex County, this park is ideal for picnics, beach walks, nature hikes, and bird watching.
Afterwards you can start heading to the Essex County wine trail! On your way toward the wineries, stop at Ure’s Country Kitchen. Much more than a typical roadside fuel stop, this hidden gem features an indoor restaurant (blueberry pancakes are a must), an ice cream parlor, and a top-tier mini-golf course that is perfect for a summer afternoon.
Tasting Along the Wine Trail
Once you have completed your friendly mini golf course competition at Ure’s County Kitchen it’s time to head to the EPIC Wineries of Essex County. Essex County has an acclaimed wine trail featuring 20+ distinct wineries. Highlights to visit include:
- Muscedere Vineyards: Family-run estate offering excellent handcrafted wines and wood fire pizza.
- Vivace Estate Winery: A beautiful spot to sample premium wines with beautiful photo ops on the property, perfect for a family picture.
Windsor’s wine country delivers a world-class tasting experience right in Detroit’s backyard, with the added benefit of favorable exchange rates for U.S. visitors.
Walkerville Distillery District Night Market
Conclude your day back in town at the Walkerville Distillery District Night Market. Held on select Fridays in the summer, this lively community gathering is a wonderful place to shop from local artisans, sample street food, and enjoy live music.
Day 3: Farmers Markets, Shopping & Panoramic Views
Saturday Morning Downtown
It’s your final day in Windsor, and after checking out of your hotel, you can begin your final day at the bustling Downtown Windsor Farmers Market, open late March through end of October each year. Grab a fresh coffee from Verde Cafe while browsing produce, artisan crafts, and local treats. Afterward, pop into Whiskeyjack Boutique to pick up unique souvenirs and Canadian-made goods representing all provinces across Canada.
Erie Street Culinary Highlights
Head over to famous Erie Street for lunch. While known for its historic Italian dining, it is also home to Erie Street Gastropub, an incredible Asian fusion spot serving some of the best culinary dishes in the city. After lunch, grab an iced matcha at Lotus & Lattes, located just behind the gastropub.
Gordie Howe International Bridge Observation Area
Before making your journey home, drive over to the Malden Park Observation Area. As the highest point in Windsor, it offers breathtaking views of the new Gordie Howe International Bridge as well as the sweeping skylines of both Detroit and Windsor.
Plan Your Visit
From scenic waterfront parks and world-class wineries to rich culinary experiences and vibrant street markets, Windsor and Essex County offer an unforgettable getaway just minutes across the border. Start planning your itinerary today!
Click here to see more highlights of the visit!
Original blog post by It’s Raquel
