Bold Red & Blue Skies. City Streets & Country Getaways. Hidden Trails & Open Waters. W.E. have it all in Windsor Essex! Plan a road trip to Windsor Essex this summer – whether it’s the city sights in Windsor, wineries and rural shops in Essex County or a trip to Pelee Island to experience the island life, we got it all here!
CHECK OUT OUR VISITOR GUIDE
Check out our Official Visitor Guide by clicking here – packed with info and tips on the best things to see & do when you plan your trip. It’s your #1 resource when you’re planning a trip to Windsor – featuring itineraries, must-do lists, partner listings and more.
You can also click here to request a print version to be mailed directly to you.
You can also check out our Summer Event Guide for a list of must-see events happening all summer long.
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WIN A ROAD TRIP EXPERIENCE
Enter today for your chance to WIN A road trip to Windsor Essex. Just click here and you could be in the draw for the chance to win 1-of-3 experiences, including:
- a stay at Caesars Windsor, a show at the Colosseum and dining experiences across the city
- a rural stay in our wine country including a The Grove Hotel, winery experiences and on-the-water adventure
- a stay on Pelee Island (in 2026) including winery experiences and a disconnect with nature adventures
Share the contest on your social media channels for bonus chances to win. You can enter once per day per valid email address. Contest closes September 30th, 2026.
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WE’RE EASY TO GET TO!
By plane, train, or automobile, we’re easy to get to!
Windsor International Airport Your Quick Gateway (YQG), is conveniently located just 15 minutes from downtown Windsor. The airport offers frequent service to and from Toronto in under an hour with Porter Airlines, Air Canada Jazz, and seasonally with WestJet. Upon arrival, transportation to and from the airport is easy with major rental car, taxi and public transit just steps from the luggage terminal. For more details visit yqg.ca
With trains operating 4 times daily between Windsor and Toronto, riders can sit back and relax (with wifi) and travel with comfort and ease. VIA Rail provides intercity passengers with fast, convenient and affordable service, downtown-to-downtown between Canada’s largest business centres. Upon arriving at the Windsor Via Rail terminal, you will find yourself steps away from the Walkerville district and walking distance to exceptional food, drink and entertainment. The station is centrally located and an easy transfer to a taxi or car service will get you to where you need to be!
Looking to be on your own schedule or have the flexibility to explore more than one Windsor Essex neighbourhoods or towns? A short four hour drive down the 401 will have you here in no time. Windsor Essex boasts plenty of free or low cost parking options for you once you are here so having your vehicle will certainly not impede on your budget while offering you the freedom to explore everything from authentic cuisine in Leamington and perfectly instagrammable coffee shops in Amherstburg, to the EPIC Wine Route and the Barrels Bottles & Brews Trail and everything in between!
MORE VALUE FOR YOUR DOLLAR
We have some great value added ways to make your trip affordable. Check out some of the options below by clicking the icons, including:
- A Flight Log tasting passport which will guide you to 13 breweries, cideries and distilleries in Windsor Essex. If you purchase a 7 day passport it will give you a tasting at 9 stops of your choice for $40 – which would normally cost approximately $90!
- An EPIC Wineries Digital Tasting Pass which will guide you to 12 of our wineries in the Lake Erie North Shore wine region. If you purchase a pass it will give you a tasting at 6 stops of your choice for $50 – which would normally cost approximately $90!
- Check out our Dining Offers page for specials, discounts and more at select restaurants in the Windsor and Essex County
WHAT PEOPLE ARE SAYING ABOUT US
Sometimes the best way to learn about what is happening is from people that have already visited! Check out our blogs and reels from people that have visited Windsor before – telling authentic stories of our region and what makes us the perfect road trip or weekend escape! You can use their blogs and reels to help craft your own itinerary, or use our Official Visitor Guide for more trip inspiration.
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WHAT’S GOING ON
Looking to find out what’s happening when you plan your visit? We got you covered! Check out our event calendar for awesome events you won’t want to miss – or check out our list of curated Buyable Experiences. These will take you behind the scenes to offer you some of the best sights, sounds and tastes of Windsor – from on-the-water adventures to foodie finds to unique cultural adventures!
UNIQUE BUYABLE EXPERIENCES
Outdoor Adventure
Unconquered Electric Bike Wine Tour
Unconquered Custom Electric Bike Wine Tours$220.00
CHECK OUT AN EVENT
MORE WAYS TO EXPLORE
Our itineraries and passports are easy ways to make the most of your trip! Click on the icons below for free ways to explore – from our W.E. Heart Local Pass guiding you to farm-to-table finds, our Follow the Flavours pass featuring tasty foodie finds, W.E. Bird Trail with spots to find our feathered friends or the CROSSROADS Historical Guide taking you to historic relics across region our passports are free, totally digital, and use your GPS on your phone to guide you to each stop! You can find more guides and passports in the region by clicking here.
DOWNLOAD AN ITINERARY
Entertainment
Slots, Shops & A+ Entertainment: An Evening at Caesars Windsor
Arts & Culture
Rag Tops & Retro Fun: A Blast From The Past In Essex County
Entertainment
Skylines & Vineyards: Shop ‘Til You Drop In YQG
Entertainment
Slots, Shops & A+ Entertainment: An Evening at Caesars Windsor
Arts & Culture
Rag Tops & Retro Fun: A Blast From The Past In Essex County
Entertainment
Skylines & Vineyards: Shop ‘Til You Drop In YQG
Still need trip inspo? Check out 12 ways to make your road trip more worthy with a few more things to do in Windsor Essex!
Use this as a checklist of what to do when you plan your next road trip!
12. HEAD TO THE TIP OF CANADA
You can literally walk out to the mainland point of Canada at Point Pelee National Park! Plan your trip to explore beaches, one of the most diverse eco-systems for plants and animals in Canada, and hike to the tip for a truly unforgettable and unrivaled Instagram experience in all of North America! Bonus tip: plan a trip during one of the dark sky night events when a new moon arrives and see the moon and stars from the park – open late for extra viewing pleasure each Dark Sky Night date.
11. VISIT WILLISTED MANOR
Walls made from whisky! Built originally in 1904 by Hiram Walker for his son, take a tour of Willistead Manor and the park surrounding it to learn more about the history of Walkerville and Hiram Walker. Tip: come during the Christmas Season to view the manor decked out in thousands of Christmas decorations to get you into the holiday spirit.
10. MAKE A SPLASH AT ADVENTURE BAY FAMILY WATER PARK
The largest waterpark in Southern Ontario and located no more than 4 blocks from all of our downtown hotels, it’s the perfect stop for the family. Don’t forget to buy a pass on the Flowrider – your chance to surf indoors, and 1-of-8 in Canada.
9. GRAB A SLICE OF CANADA’S BEST PIZZA
Pizza is a BIG deal in Windsor – and you MUST grab a slice when you visit. And we’re not lying: we won best in Canada and best in the world! Try it for yourself at one our our local spots and see our preferred list at www.windsorpizzaclub.ca and learn about what makes Windsor-style so unique. In crust we trust!
8. SIP Our Coffee Culture
Our coffee shops are more than just your regular double double. Check out our roasters and artisanal coffee shops and talk with our baristas who will share their passion for the perfect brew.
7. PLAN AN ISLAND ESCAPE
Head to Pelee Island for a true island escape. After a 1.5 hour ferry ride from the mainland you’ll find Pelee Island with pristine beaches and a remote escape (it’s true – cell phone access is spotty at best). Click here and read our Know Before You Go blog and plan a truly relaxing escape for a day trip, or an entire week at one of the quaint cottages. And a stop at Pelee Island Winery (Canada’s largest estate winery) is a must – calling Pelee Island home.
6. A NEW MEANING TO ‘SUP
Explore our 100 mile coastline by the power of the paddle. Whether its by canoe, kayak or by stand up paddleboard (SUP), we have stops all along the shore to make the most of our waterways. Click visitwindsoressex.com/paddle for more details.
5. TAKE A SELF GUIDED TRIP ON THE BARREL TRAIL
Check out the Flight Log and explore the 11 breweries and 2 distilleries that are part of the Barrels Bottles & Brews Trail. A Flight Log will cost you $25 – and gets you an exclusive offer on a flight of craft beer or spirits at each stop. Check out what you could experience.
4. MAKE IT AN EPIC ROAD TRIP
Did you know that Windsor Essex features Canada’s hottest wine region – our Essex Pelee Island Coast wineries, or as we call them ‘EPIC’. Plan a trip to explore the 20 wineries dotting the lakeside featuring crisp whites, soft roses, perfect bubbles and bold reds rivaled by the rest of the wineries across Canada. Click here for more details including our wine route map and plan your next trip by car or by bike!
3. EXPLORE CANADA’S LARGEST CASINO RESORT
Come explore Canada’s largest casino resort – from non-stop action on the gaming floor to world class accommodations and world class entertainment weekly inside the 5,000 seat Colosseum. Make it a day trip, a night, or a weekend (including some fun inside Ariius nightclub) all under one roof!
2. TASTE LIQUID GOLD
Did you know that Windsor is the home of Canadian whisky – and North America’s largest distillery is located right along the Detroit River in Windsor. Visit the J.P. Wiser’s Experience and purchase a bottle of limited edition spirits to take home with you.
1. EXPLORE BY THE POWER OF THE PEDAL
There are miles of trails in our region – perfect for a two wheeled adventure. Check out www.visitwindsoressex.com/bike for our Cycle Tourism Map featuring six trails, and bike-friendly certified stops along each trail.
If you wanna stay up to day on our region you can also sign up for our newsletter to get info, details and more about our region directly to your inbox.
