This travel guide I put together is especially meaningful to me. Windsor Essex has always been like a second home. I grew up spending every summer there with family, and even as an adult, I drive down from Toronto to Windsor to celebrate Christmas with family every holiday season. This city holds so many cherished memories, from childhood adventures at Devonshire Mall to holiday traditions around the Christmas tree. My family even owns Red Sail Restaurant, a local institution that’s been serving up the best Chinese food in the city since 1972! Over the years, I’ve come to know Windsor and Essex County like the back of my hand, and I love sharing its hidden gems with anyone looking for a fantastic getaway. Whether you’re a foodie, an adventure seeker, or someone who just loves a great weekend escape, this guide has you covered! Windsor isn’t just a place I visit, it’s a part of who I am. I’m so excited to put together this travel guide for you all and share this very-much underrated city in Ontario just a 3.5 hours drive away from Toronto.
Where to Eat
The Vines Restaurant at Cooper’s Hawk Vineyards
Start your Windsor-Essex adventure with an unforgettable dining experience at The Vines Restaurant, located within the picturesque Cooper’s Hawk Vineyards. Celebrated for its locally inspired cuisine and award-winning wines, this restaurant offers a warm yet refined setting ideal for a farm-to-table meal. The vineyard is a sight to behold, with rows of grapevines stretching into the horizon. I had the most incredible cod dish - bursting with colour and flavour with a beautiful pea green puree - and the chocolate mousse, recommended by our server, was absolute perfection. One of the best desserts I’ve had in years! And of course, with a vineyard setting, their expertly paired wines are a must.
River Room Restaurant
For a perfect evening wind-down, head to River Room Restaurant for handcrafted cocktails paired with unmatched waterfront views. Located on the second floor of the Best Western and DoubleTree Hotels, this hidden gem might just offer the best panoramic view in all of Windsor. The intimate yet lively atmosphere is elevated by floor-to-ceiling windows that showcase the glittering Detroit skyline. Sip on one of their signature cocktails or mocktails, mixed with premium spirits and fresh ingredients, or stick with a timeless classic that never misses.
Café Amor & Art
Ease into your day at Café Amor & Art, a charming café that combines delicious breakfast with artistic flair. The cozy space is filled with vibrant murals, local artwork, and pottery, creating a warm and inviting vibe. Their Mexican-inspired specialty coffees and homemade pastries are a treat - I had the Matcha Latte and Mexican Chilaquiles, and it was the perfect way to start the day. The friendly staff made the whole experience even more memorable. I took a seat right by the front window in the comfiest chair and I just didn’t want to leave! This cafe is a must visit for sure!
Zuleeats
Craving something savoury on the go? Swing by Zuleeats for their beloved hand pies. Specializing in traditional Ghanaian savoury meat pies, they also offer tasty vegetarian and vegan options. Each pie is packed with flavourful fillings wrapped in a golden, flaky crust - perfect for snacking between stops. Can’t make it to their storefront on Howard Avenue? You can also find them at the local farmers' market every week until October. These are perfect hand pies to take home and re-heat in the oven, making it a easy meal to prepare when you are pressed for time. Simply delicious!
Wolfhead Distillery
Elevate your lunch plans with a visit to Wolfhead Distillery, where craft spirits meet culinary creativity. Famous for their small-batch whisky and vodka, Wolfhead serves up a delicious menu designed to complement their drinks. Their Old Fashioned is a local favourite, with bold, smooth flavours and just the right touch of sweetness. After your meal, join a guided tour to learn about their handcrafted distilling process. Don’t leave without trying their Banana Caramel Vodka or Coffee Whisky Liqueur - both are out of this world! With its rustic-modern vibe, this spot is a must for food and drink lovers.
Armando’s Amherstburg
For dinner, indulge in a slice of Windsor tradition at Armando’s Amherstburg, home to some of the region’s best Windsor-style pizza. What makes it Windsor-style? Think shredded pepperoni, canned mushrooms, and premium Galati cheese on a perfectly hand-tossed crust. The result is a pizza that’s crispy, chewy, and totally unforgettable. Not a pizza person? Their menu also features hearty pastas, fresh salads, and other Italian favourites. This restaurant was even featured in a CBC documentary called “The Pizza City You’ve Never Heard Of!”
Sandwich Brewing Co.
End your Saturday night at Sandwich Brewing Co., a cozy craft brewery set in a beautifully restored historic building. Known for their top-quality, small-batch beers, this local favourite offers everything from hoppy IPAs to rich, smooth stouts. Whether you grab a seat on the ground floor, upstairs, or out back on the dog-friendly patio, the vibe is always welcoming. Bonus: they serve unlimited complimentary popcorn - because what goes better with beer than that? Also, if you are looking to get married soon and looking for a venue, Sandwich Brewing Co hosts countless weddings every single year!
Tabouli by Eddy’s
In the heart of Tecumseh, Tabouli by Eddy’s (Manoushii) offers a hearty and authentic Lebanese breakfast experience. Specialties include freshly baked flatbread topped with za’atar and cheese, rich shakshuka, fig with halloumi, and the comforting fattet hummus. This isn’t your typical eggs-and-toast brunch - it’s a flavourful journey through the tastes of the Middle East. Pair your meal with a bold Turkish coffee to jump start your day with energy and warmth. This meal right here was basically a Lebanese feast. A perfect start to the day!
Grand Cantina
For bold flavours and an upbeat vibe, make your way to Grand Cantina in Walkerville. Famous for its tacos, tequila, and globally inspired menu, this hotspot delivers a colourful and dynamic dining experience. Their gourmet tacos and Mexican street food are full of personality and flavour, and the Duck Fat Fries are an absolute must. Don’t forget to order a chilled margarita and take in the eclectic decor. From vibrant bar tiles to eye-catching art, every meal here feel like a celebration. You’ll be able to taste and travel to Mexico right here in Windsor without ever having to buy a plane ticket.
Thai Palace
Wrap up your Windsor-Essex getaway with a delicious dinner at Thai Palace, where authentic Thai flavours meet exceptional hospitality. The richly decorated space - complete with traditional tapestries and ornate sculptures - transports you straight to Southeast Asia. Whether you're enjoying a spicy curry, a warming bowl of glass noodles, or my personal favourite, the Tom Yum Soup, this spot offers a deeply satisfying and memorable dining experience. As the saying goes, there’s always room for dessert. So don’t forget to order their signature Mango Sticky Rice to end your meal.
Cookie Bar
Looking for a sweet finale? Cookie Bar is a must-visit for dessert lovers. Specializing in massive quarter-pound craft cookies, this bakery is known for its crispy edges, gooey centers, and indulgent flavour combinations. Each cookie is baked fresh using premium ingredients, and with seasonal varieties always in rotation, there’s something new to crave each time. I tried their seasonal Black Forest cookie and it was phenomenal. Bonus: you might even catch a sighting of Cookie Monster himself while you're there! He is hard to miss believe it or not.
Chance Coffee
A haven for coffee aficionados, Chance Coffee in Ford City is dedicated to quality and sustainability. Their beans are ethically sourced and roasted on-site, resulting in some of the region’s finest coffee. Whether you’re in the mood for a pour-over, a bold espresso, or simply a cozy corner to relax, this spot delivers. The space is quaint and welcoming - perfect for catching up with friends, grabbing a drink to-go, or getting a little work done with your laptop in tow.
What to Do
Willistead Park
A lush and historic green space, Willistead Park is home to over 300 trees, including Windsor’s only persimmon tree and several rare species. Wandering its peaceful paths feels like stepping into a hidden oasis, where majestic Shumard oaks, London Planes, and Kentucky coffee trees line your route. Be sure to visit the Paul Martin Gardens for a quiet moment among manicured hedges and vibrant blooms. Whether you're enjoying a casual stroll or attending the annual Art in the Park festival, Willistead is a must-see when the gardens are in full bloom.
Urban Art Market
This creative boutique in Windsor Essex is a celebration of local talent, featuring handmade goods from over 30 artists and makers. From delicate pottery and cozy knitwear to whimsical greeting cards and statement jewelry, every piece tells a story. Shopping here is more than just browsing - it's a meaningful way to support local artisans and take home something truly special. After browsing through the various items here, a fragrant lavender candle won me over and is now sitting at home on my table.
Jones & Company
Nestled in Walkerville, Jones & Company is a charming boutique offering an eclectic mix of stationery, home decor, toys, and accessories. The shop is a treasure trove of beautifully curated items, from elegant candles to playful socks. Personally, I bought the cutest mushroom salt & pepper shakers here to take home! Bonus tip: it's the only licensed retailer in Windsor-Essex for Jellycat plush toys - perfect for kids and collectors alike!
Bunch
A cozy, curated shop filled with home and body goods, Bunch specializes in warm, nostalgic finds from independent designers and artisans. You’ll discover everything from sustainable candles to locally made soaps, plus a wide selection of vinyl records and stylish apparel. Co-owned by Matty Morand, a member of indie-rock band PONY, this spot hits all the right notes for music lovers and thoughtful gift-seekers alike. What did I buy here? A beautifully made dog leash for my Samoyed Yoshi!
Park House Museum
Step into the 1850s at the Park House Museum, where immersive hearth cooking demonstrations bring the past to life. Learn how meals were prepared over open flames using traditional techniques and period tools. The aromas of wood-fired dishes transport you to a time before modern conveniences, offering a unique glimpse into domestic life during Windsor’s early years. The museum also explores fur trading, local history, and Victorian living. I had so much fun taking part in the hands-on cooking demonstration where we made a Victorian Sponge Cake, a favourite recipe of none other than Queen Victoria herself! The best part is you get to enjoy that slice of heaven after it gets cooked in the 18th century oven, and let me tell you, it was absolutely delicious!
Ford City Murals
Explore Windsor’s history through art with the vibrant Ford City Murals. Spread across 20 locations, these 36 large-scale murals celebrate the city’s automotive legacy, industrial roots, and diverse cultural identity. It’s an open-air gallery that doubles as a walking tour, perfect for history buffs and art enthusiasts alike. Check out the mural guide to help you plan your visit and uncover each stunning piece to ensure you don’t miss any of them along the way. There are also so many amazing local businesses along this street, so even if you get a little lost wandering the streets, you just may end up in a cute cafe or store and there ain’t nothing wrong with that.
Where to Stay
Best Western Plus Waterfront
For a comfortable and convenient stay, I highly recommend the Best Western Plus Waterfront. Located in downtown Windsor, this hotel offers stunning panoramic views of the Detroit River - something I personally can’t get enough of, especially when the river sparkles under the sun and city lights at night. With its prime location, you're just steps away from restaurants, attractions, and nightlife. The hotel features fast Wi-Fi, a complimentary hot breakfast buffet, a scenic fitness center, and a saltwater pool, ensuring you have everything you need to relax and recharge. I don’t think I ever been so close to the water before staying at a hotel. It looked like we were floating on top of the water as I looked out the window. What a view it was!
Windsor-Essex is a place that truly feels like home to me, and I’m excited to share its incredible food, hidden gems, and welcoming atmosphere with you. Whether you’re here for a quick weekend escape or a longer adventure, this region offers something for every traveller. So pack your bags, bring your appetite, and get ready to discover the charm of this special corner of Ontario! I’ll see you all here at Christmas time!
