Choose Your Own Road-Trip Adventure in Ontario’s Southwest



© Dudek Photography

Explore Ontario’s Southwest

Whether you’re seeking a relaxing rural retreat or an urban adventure, Ontario’s Southwest offers the best of both worlds. This destination allows you to explore off-the-beaten-track areas around an emerging hotspot for wine, beer, and cider paired with a variety of metropolitan activities. Enjoy a laid-back coastal vibe with friendly locals, blending guided tours and outdoor fun. This getaway truly combines a taste of rural charm with urban excitement.

If your adventure begins in Windsor, crossing the border is quick and easy—the Detroit-Windsor tunnel into Canada is a direct link to Downtown Windsor and a short drive from nearby highways. Don’t forget your passport! Popular accommodations include Caesars Windsor Hotel, DoubleTree by Hilton Hotel & Suites, Towneplace Suites and A Hidden Gem Bed and Breakfast. Each accommodation is close to the excitement the region has to offer and allows for a relaxing place to lay your head after a day of exploring.

To kick off your trip, explore Point Pelee National Park. Take the shuttle to The Tip—an hour round trip—and enjoy the beauty prevalent at the national park. Supporting a mosaic of habitats from jungle-like forests to lush wetlands to open Savannah, Point Pelee is an exciting place to explore.

After leaving the serenity of the southernmost point of mainland Canada, make a stop at Pelee Island Winery. With more than 750 acres of vineyards, Pelee Island Winery is internationally recognized and its vines are part of Canada’s longest growing season, thriving amidst the combination of sun, soil, lake, and latitude.

ontario's southwest
© Dudek Photography

Take advantage of the fact that you’re in one of Canada’s most scenic spots for wine touring and spend a few hours exploring. If you’d like to set your own course, pick up an EPIC Tasting Pass to enjoy tasting flights at six local wineries—including Pelee Island Winery. Grape Vine Tours is an excellent option for those who prefer to have someone else set the route. The wineries offered with the Tasting Pass are part of the region’s EPIC Wineries, some of which include Colio Estate Winery, Oxley Estate Winery, VIN Winery, and so much more.

If you’d rather get a taste of the many craft breweries and distilleries in the area, a Flight Log is your ticket to five tastings at 13 different stops along the Barrel Trail.

Looking for a different beverage to end your day? No problem, whisky lovers will want to get experiential with J.P. Wiser’s Master Blender Class where you’ll learn, create, and blend your own custom whisky just for you!

When you’re ready for a delicious dinner, Windsor-style pizza is a must-try. Here are some top picks for restaurants where you can savor this local specialty: Antonino’s Original Pizza, Armando’s Pizza, or O.G. (Original Guys) Pizza.

Embrace Windsor’s urban side by enjoying a night out at the symphony or a show at Caesars Windsor, or an evening stroll through the Windsor Riverfront Sculpture Park. Windsor has become an exciting arts destination, thanks in part to outdoor galleries that are taking over the city. To explore the abundance of public art in the region, sign up for a tour led by a local. Tours include stops in Artist Alley, Windsor Sculpture Park, WIFF Alley and more.

If you’re looking to get in tune with history, take a tour of Willistead Manor, a 36-room mansion built in 1906 for Edward Chandler Walker, the second son of Hiram Walker, founder of the world-renowned distillery. You can even take home a Willistead-themed souvenir as a reminder of the historic home.

For a broader look into the history of the Windsor area, visit Museum Windsor – Chimczuk Museum, which features a state-of-the-art children’s gallery, a look into the Original People’s culture and legacy, and more.

Before leaving Windsor, sneak in a few last stops to browse for a unique keepsake to help remember your trip. You’ll find beautiful handmade items at Urban Art Market. If you’d prefer to make your own memento, consider a class at Sketch Clay + Pottery or a make-your-own charcuterie board workshop at Michael Difazio’s Reclaim Artistry.

Next, make your way to the friendly lakeside town of Kingsville. As it’s about an hour’s drive from Windsor, you’ll likely wish to stay in the area. Excellent accommodation choices include Distinctive Inns of Kingsville, The Grove Hotel & Motel, The Walnut Grove Bed and Breakfast, and the Magnolia Ranch.

History also comes alive at the Canadian Transportation Museum and Heritage Village, which showcases a diverse collection of restored buildings from the 1700s to the 1920s that transport you back in time.

© Jess Baumung

Once you’ve had a chance to settle in, explore Kingsville to find a place for dinner that strikes your fancy. There are many great options in the area such as The Goose Kitchen and Bar, Mettawas Station, El Diablo, and Taphouse 127 – Restaurant By Kingsville Brewery.

Continuing on your journey, head towards Sarnia stopping on the way at the Oil Museum of Canada. Get an close-up look into the oil industry and its history in the region, visiting the first commercial oil well in North America, a blacksmith shop, and more. Since opening in 1960, the museum has shared interesting stories of oil heritage.

Don’t miss a trip to Victoria Playhouse Petrolia for exciting live shows that theater-goers will love.

When you arrive in Sarnia, you’ll have your pick of great hotels like The Insignia. There are also lots of great options for food in the area, such as Big Fish Steak and Lounge or Refined Fool’s Sports.

Located in the center of Sarnia’s downtown cultural district, the Judith and Norman Alix Art Gallery offers an eclectic range of exhibitions, tours, lectures and programs. The gallery’s permanent collection comprises some 1,200 Canadian historical and contemporary works, including work from the Group of Seven.

Get in touch with your green thumb at Forest Glen Herb Farm and Bed & Breakfast. Their classes and workshops teach you how to grow your own vegetables and fruit, or you can make your own jam, tea, or potpourri.

Ontario’s Blue Coast is home to the Cheers to the Coast trail, which includes breweries, wineries, cideries and more such as Widder Station Tap House, Alton Farms Estate Winery, Munro Honey and Meadery, and Shale Ridge Estate Winery and Cidery.

If you’d prefer to let someone else drive and plan your route, Ride The Bine’s Huron and Lambton tour options are for you! You can choose between pre-set full-day and half-day tours or book a custom tour to visit your choice of stops. Wave Limo & Tours also offers a variety of wine, beer and cider tours in the area.

For a night out on the town, enjoy a show at Imperial Theatre, or test your luck at Starlight Casino Point Edward. Imperial Theatre has a collection of shows that range from kids’ shows, cover bands like Abbamania, and shows that are fun for the whole family. Starlight Casino Point Edward offers more than 450 slot machines, and your favorite table games.

Explore what makes southwestern Ontario so special at Lambton Heritage Museum. Nestled in a unique oak savanna habitat, the museum grounds are as captivating as the museum itself. Walk the nature trail and soak up the beauty before diving into the history inside the museum.

If you wish to stay in Grand Bend, you’ll have a variety of excellent accommodation options for the evening such as The Kiwi Motel, The Colonial Hotel, or the Oakwood Resort. You’ll be staying close by great local eateries such as Lake Hound or The Tipsy Pelican.

© Dudek Photography

Looking for more things to do in the area? Gauge how active you’re feeling, and then enjoy one of the following activity options:

  • Stroll the streets of Grand Bend and do a little shopping.
  • Rent cross country skis or snowshoes at Pinery Provincial Park.
  • Explore the Oak Savannah and Carolinian forest on the network of hiking trails at Lambton County Heritage Forest in Pork Franks.

The benefit of starting in Windsor and ending in Grand Bend means that you will have a different route home than you traveled on the way there. You can choose your own adventure based on the activities that stand out most to you—get ready to experience 30 percent more on this trip with a favorable exchange rate. Whatever you choose, you’re in for a relaxing rural drive with plenty of pretty scenery along the way, no matter which way you’re headed. Once you have decided what you want to do, you’ll want to take a moment to plan out the most efficient driving route in advance.

Find out what responsible travel means to Ontario’s Southwest by reading their Responsible Travel Pledge at

Get your free copy of Global Heroes, jam-packed with positive news, straight in your inbox.

Your subscription could not be saved. Please try again.
Your subscription has been successful.

Combine the shorelines of Lake Erie, Lake Huron, and Lake St. Clair offering up world-class freshwater beaches, the rich biodiversity of the Carolinian Forest region, with bountiful farmlands creating a rapidly evolving beverage and culinary scene, the friendliest communities on the planet, and you get Ontario’s Southwest! Now that we’ve let you in on the secret, it’s time to come and discover it for yourself.


Subscribe to our Newsletter and Access all issues of Global Heroes News straight in your inbox. 100% free, no purchase necessary, for life. Uplifting stories, highlighting the inspirational efforts of everyday people, celebrities, and organizations, who are diligently working together towards practical solutions to global problems.