A Perfect Weekend in Windsor Essex
If you’re looking for a getaway that includes exploring, enjoying small historic towns, and wine tasting, Windsor Essex is the perfect place. Picture serene lakeside views, charming local wineries, and friendly faces greeting you at every turn. This was the perfect way to explore Southwestern Ontario for the weekend, and it is just a 4 hour drive from the Greater Toronto Area.
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Things to Do
One of my favourite stops was visiting the historic Amherstburg, a charming town that was awarded the “Best Street Festival” at the Best of Windsor Essex Awards. The community has century old buildings, and the waterfront is a beautiful place to take a stroll. The waterfront trail is incredible because there are so many different monuments and areas to enjoy. One of the highlights is the historic Navy Yard Park, which played a big role in the War of 1812.
Open Air Weekends is a street festival held in downtown Amherstburg, with lots of fun weekend activities. This vibrant street festival happens all summer long. There are so many lovely shops to explore with local businesses selling home decor, jewelry, candles, and a lot of great eateries. I loved the vendor markets here, as well as the bagpipe parade, Bagpipes in the Burg, which was amazing to watch. The streets really come alive here during Open Air Weekends, and it’s a great place to stroll and enjoy the atmosphere.
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Streetcar 351 and Sculpture Park
I absolutely loved the riverfront area in Windsor, this was a lovely stretch of the city. Known as one of the city’s most scenic spots, and it truly is the perfect place to slow down and take in the beautiful views. The Sculpture Park is a 5km trail with 31 contemporary sculptures by world-renowned artists. This amazing open air museum is free to enjoy along the waterfront and the views of the Detroit skyline.
One of the highlights along the riverfront is Streetcar No.351, a beautifully restored streetcar. Once part of Windsor’s waterfront transit system, this restored 1918 streetcar now stands as a proud icon of the city’s transportation history. This free site is a great spot to explore and then grab a coffee and enjoy the terrace at the Legacy Beacon. I enjoyed learning more about the history of Windsor’s transportation system and was impressed with how well the streetcar has been preserved.
The Windsor waterfront offers a beautiful cultural and scenic escape in the heart of the city.
EPIC Wine Fest
I was lucky enough to be visiting the same weekend as the annual EPIC Wine Fest! The event brought together wineries from the region, offering the chance to sample a variety of local wines and delicious food pairings from the different food trucks set up. We even got the cutest souvenir glasses to take home! The LaSalle Event Centre was the perfect venue, offering both indoor and outdoor spaces that created a great setting for a day filled with wine, food, and fun. The wine region here is so unique because of the climate, the EPIC (Essex Pelee Island Coast) wine region is the Southernmost wine region in Canada, and is located on the same latitude as northern California. The terroir and mild season makes it perfect for wine growing.
Where to Stay:
I stayed at the Hyatt Place Windsor, a brand new property that is less than 1 year old and the location was perfect. Situated close to the highway, and in Windsor, and it was close to everywhere we were exploring. The property was so clean and modern, I loved the way the rooms were decorated and thoughtfully designed. Everything felt fresh, contemporary, and very spacious. The property is dog-friendly and well-equipped, and guests can enjoy complimentary breakfast, free parking, and amenities such as an indoor pool and fitness center. I highly recommend basing at the Hyatt Place Windsor for a comfortable stay.
Where to Eat & Drink
Wolfhead Distillery
This spot specializes in handcrafted small-batch vodka, whiskey and gin, and they have delicious items on their menu. Some of the menu items are even infused with the spirits! The craft cocktails were delicious, and I loved the Cajun Beef Tips as well as the famous fried Lake Erie Perch. The patio is beautiful, and is a must visit in Amherstburg!
The G.O.A.T Tap & Eatery
With its lively atmosphere and modern sports bar feel, this spot covers all the classics from burgers, wings, and bar food. The burger and philly cheesesteak were a must try!
GL Heritage Brewing Co.
Windsor Essex is known for its wineries, but this brewery was one of my favourite spots as they create high-quality handcrafted beers in a welcoming setting. The tasting room is bright and inviting, and outside they have a beautiful sunroom and patio. I had the chance to tour the brewery and chat with the co-founder, Greg, who shared how deeply rooted the business is in family and community. The brewery is located on century farmland that has been in the family for over 175 years. The brewery name pays tribute to Greg’s father and his business GL Heritage Motors that he opened with his close friend. I loved learning more about this incredible business, the legacy, and their principles – “family, friends, and good times come first”. You truly feel this during your visit, between the warm hospitality, the thoughtful storytelling, and of course the excellent beer.
Dancing Swallows Winery: One of the most charming stops along the EPIC Wine Route, is Dancing Swallows, a beautiful micro-winery that blends rustic charm and a laid-back, welcoming environment. The tasting area is under a beautiful maple tree, creating a relaxed environment where you can feel the breeze, and try their amazing wines. Their small-batch wines are produced with care, and are on the dryer side. They highlight the local terroir, and my favorites include the Mary’s Lane Red and the Riesling.
Windsor Essex is such an incredible region, there is truly so much to do and I can’t believe it took me this long to visit. I am so happy I visited and got to explore and really fall in love with the region. If you want a weekend getaway filled with great food, history, small towns, shopping, and wine, you must check out the Windsor Essex region. From wine lovers, foodies, history buffs, or to those simply in search of a peaceful getaway, Windsor Essex truly has something for everyone. I can’t wait to return to this beautiful area, and explore again!
Click here to view more of Tilly’s visit to the region.
Click here to see Tilly’s favourite highlights from her visit to EPIC Wine Region!
Original Blog Post by Tilly’s Travelling Table.
