Discover Windsor

As social distancing measures continue to relax, what better way to unwind than a relaxing retreat to Canada’s South – Windsor & Essex County!

When you start planning your road trips for down the road, we want you to think about Windsor Essex. It’s a rural retreat – a big city with small town charm. Boutique hotels, owner operated restaurants, farm fresh dining, cultural delights, and it’s all just a 3.5 hour drive from downtown Toronto. Check out more below!

Note: due to COVID-19 safety precautions, some establishments are temporarily closed as they learn to adjust to new social distancing measures. We suggest you contact the businesses prior to planning a trip as their services and hours may be modified.

How to Get Here

Windsor is easy to get to – by plane, train or car. Expand any of the below options to find out just how easy it is!





You may not know it, but Windsor is the fourth-most multicultural city in the country. And with that come fantastic bites. Some of the highlights you MUST check out when you make a trip.

  • Windsor-style pizza: It’s known around the world for it’s thin crust, shredded pepperoni, and locally made cheese
  • Shawarma – you can find authentic around every corner. Perfect for a quick-lunch, or grab & go after the bar
  • Farm-to-table dining – Essex county has over a million+ acres of greenhouses, so that means fresh veggies are available within a 30 minute drive year around.
  • Pierogies & paczki – look for the polish delights on a lot of the menus in the region

Click here to check out more on the culinary scene in the region.


Windsor is known as the home of Canadian whisky – so you know they’re serious about their cocktails. And more! And what’s awesome about it is….their beers, wines & spirits are all local at the bars & restaurants. Check it out!

  • There are 18 EPIC Wineries along the Lake Erie North Shore – so sampling the bold reds, crisp whites and soft rose’s as a must.
  • You may know that Windsor his home to one of the largest distilleries in the world. The Hiram Walker Distillery is supplying the world with J.P. Wiser’s and Canadian Club whisky, polar ice vodka & more.
  • That means their cocktail scene is A+! Check out the Blind Owl or Maiden Lane Wine & Spirits for some of the best.
  • There are also 10 craft breweries (and more opening soon) in the region. Check out the Flight Log – where you can get an exclusive flight tasting at each stop for $25.
  • Their Coffee Culture is also something to check out. Locally roasted brews available in quaint coffee shops across the region – cold brews, fresh espresso and beans to go!


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With beautifully appointed accommodations peppered with outstanding services, like complimentary valet, concierge, indoor pool & spa, and fitness centre Caesar’s Windsor Hotel will make your stay truly unforgettable.

This CAA/AAA Four-Diamond hotel, which offers 758 guestrooms and suites overlooking the beautiful Windsor riverfront defines modern luxury and boasts six world class restaurants, three contemporary full-service lounges. and world-renowned entertainment in the 5,000 seat Colosseum theatre!

Caesars Windsor also offers non-stop slot and gaming table action!  Try your hand at Blackjack, Roulette, Mini Baccarat, Craps, Caribbean Stud, Let it Ride, Three Card, Four Card and Pai Gow Poker.


With the perfect blend of hip and historic, the Walkerville District is one of the most unique neighbourhoods you’ll find in Windsor Essex, with a rich history steeped in the rollicking days of smugglers, Prohibition and the birth of the labour unions.  With vibrant boutique shopping, dinning and craft brewing nestled among Windsor’s largest collection of heritage properties, Walkerville is a one-stop for all of your shopping, services, dining, and entertainment needs.  Attend one of the Distillery District Night Markets held monthly on the last Friday from May – October to eat, drink, shop and enjoy live music under the stars and strings of edison lights.

Visit Kingsville Main Street where boutique shops line the streets and offer an assortment of unique clothing, desserts, gifts, wellness products, gardening essentials, and so much more. Pop into one of the quaint bakeries or produce markets and get a taste of local.  Walk the trails, explore our parks and visit our beaches. Spend an afternoon biking through lush EPIC Wine County, play a round of golf on one of our championship courses or simply take in our stunning Victorian-era architecture.

Create a Custom Trip

If you’re looking to plan a trip now, check out our MyTrip Digital Itinerary Builder, or click some of the itinerary ideas below. You can create a stop-by-stop itinerary based on popular attractions, or key interests. Export it for driving directions between each of your stops!


Make your day even sweeter with take out visit to @sweet_retreat_ice_cream for a scoop (or two) for their Kawartha ice cream! We're going with a heavenly hash & moose track double scoop - what's your favourite flavour combination? #YQG #WindsorEssex #OntSouthwest #DiscoverYQG #DiscoverON #DiscoverCanada #foodie ...

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What are you sipping on?? Slip a delightful hard seltzers from @thegrovebrew into your koozie, sit back and relax! Have you discovered all the local offerings on our #BarrelTrail yet? Click to discover our 14 partners #WindsorEssex #BarrelTrail #DiscoverYQG #DiscoverON #DiscoverCanada #OntSouthwest ...

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If you're looking for the spot where fresh meets delicious look no further than @freddys_restaurant for some Lake Erie perch and perfectly crisp fries! Order your Friday fish to go and start the weekend off right! #YQG #DineYQG #WindsorEssex #DiscoverYQG #DiscoverON #DiscoverCanada #OntSouthwest #foodie ...

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