4-day Ontario road trip: Southwest and West Coast sampler

Explore the culture, history, nature, food and drink in and around Windsor.

START: Chatham-Kent
END: Leamington

A child playing with a stick on a beach during the pink sunset filled sky.

Visit Ontario’s Southwest and discover an area full of Black history, cultural experiences and beautiful beaches, including Cantera Park and Grand Bend. Windsor, Kingsville and Leamington have outstanding food, craft breweries, wineries and distilleries – not to mention unique shops and great chocolate! Not to be missed is the fantastic pizza in Windsor.

Ontario is the world in one province and is the original homelands to many nations of the First Peoples. With the Cree Nation in the North, the Haudenoshaunee in the South, and the Anishinabek Nation all around the Great Lakes, we are pleased to acknowledge and support the First Peoples and First Nations of these lands; the Inuit; and the Metis as we host visitors together.

Chatham-Kent – Day One

Begin your road trip in Chatham-Kent. Known for its rich Black history and amazing Indigenous experiences that will both tug on your heart. Follow the North Star road signage to relive some of the most heroic Black history stories ever told. ​Once considered a destination for freedom seekers, Chatham-Kent was home to some of the most successful Black settlements in Canadian History. Today, three sites contribute to the Chatham-Kent Underground Railroad story. Head on over to TJ Stables and meet one of the Anishinaabe Ojibway Spirit Horses and learn about the history of this unique breed.   

A bust on a pedestal, commemorating freedom; surrounded by gardens and standing tall is a large geometric shape artwork


Things to Do

Josiah Henson Museum of African-Canadian History (Uncle Tom’s Cabin): Through interpretive videos, interactive exhibits, numerous artifacts and tours, Uncle Tom’s Cabin gives us a lens into the Black experience Canada. 

Black Mecca Thomas Art Gallery Museum: Step inside and uncover the emotional journey of Chatham's Black community from the end of the 18th century to present day.  

Greenview Aviaries: A beautiful landscaped country park, zoo, splash pad and playground.   

A plaque with historical information introduces the landmark and house surrounded by trees

Buxton National Historic site: Follow the story of how former Black slaves found freedom in Chatham-Kent. TJ Stables Horseback Riding: Book ahead for “Awaken Your Spirit” – a three-hour Ojibwe Spirit Horse encounter where guests will learn about First Nation and Metis cultures. 

Hint: The Sons of Kent Brewing Company released a limited-edition beer honouring The Chatham Coloured All-Stars Team of 1934. Proceeds from the beer will go directly to the Chatham-Kent Black Historical Society & Black Mecca Museum. If sold out, you can still drop by to support these this great business.  


Places to Stay

Chatham-Kent has no shortage of places to stay.   

The retro style front facade along with large tree planters on either side of the door

Retro Suites is unique and definitely Instagram-worthy. A boutique, art-driven hotel, The Retro block is comprised of eight architecturally unique buildings. Each suite has a different theme, including the Easy Rider suite and the Log Cabin.   

The Holiday Inn Express has everything your family needs.  

Additional options are the Comfort Inn Chatham and Wyndham Travelodge. Both are pet friendly and offer breakfast. 


Places to Eat


Shady Pine Restaurant has been a great stop for lunch and dinner since 1940! 

Hungry Man totally known for its French toast and other great breakfasts. 


Start with a visit to Sons of Kent. Four guy-friends who grew up together in Chatham started this brewery.    

Another fantastic place that has something for everyone is Chilled Cork Restaurant and Lounge. Serving up comfort food with an international spin.   

Craves: Poutinerie Chatham is a little more casual.   


Petrolia – Day Two

Distance to Next Stop:  6 km / 35 mi  

Next stop is the Oil Museum of Canada. National Historic Site preserves the 1858 site of the first commercial oil well in North America. Visitors from around the world tour the museum to learn the story of innovation and the contributions made by Canada's oil pioneers.  

Distance to Next Stop:  Sarnia 40 km / 25 mi

No journey is complete without a stop at Stones and Bones Museum in Sarnia.It currently houses more than 6,000 objects that include Native Canadian tools and artifacts, gemstones and dinosaurs.  

Distance to Next Stop: Canatara Park and Beach 4 km / 3 mi 

Hit the beach at Canatara Park

This sandy beach in Sarnia’s Canatara Park stretches nearly a kilometre along the shore of Lake Huron near the mouth of the St. Clair River. Canatara Beach is one of only 27 in Canada to have earned official Blue Flag status. It also features mats to make the beach more accessible to people using wheelchairs or strollers. 


Places to Eat

I scream, you scream, we all scream for ice cream! Stop at Suzy's Ice Creamporium/Original Albert's

Looking for more than ice cream check out:  


Places to Stay

Insignia Hotel is a luxurious boutique hotel featuring 84 rooms that come complete with Frette robes, L’Occitane amenities and a Nespresso. 

Hampton Inn by Hilton Sarnia/Point Edward is a new Sarnia hotel located near Bluewater Bridge International Border Crossing. 

Distance to Next Stop:  Grand Bend Beach 74 km / 46 mi 

A man and woman stand on top of a viewpoint, watching the blue beach waves

Grand Bend certainly deserves its reputation as one of Canada’s best. Grand Bend’s Main Beach is one of only 27 in Canada to have earned official Blue Flag status. It also features mats to make the beach more accessible to people using wheelchairs or strollers. 

Hint: Main Beach visitors can join in the crowded scene or find a quieter experience on the South Beach.  

Hint: Make sure to check the municipality’s web cameras to ensure the beach isn’t too crowded before you head out. 


Places to Eat

The Lake Hound Grand Bend is a great place to enjoy a cold drink, vegan and gluten-free meals and of course, a beaver tail.  

Midori Sushi Bar & Restaurant serving Japanese fare & specialty sushi rolls. 

F.I.N.E a Restaurant is a casual fine dining restaurant with a wonderful menu filled with regional cuisine daily specials, and local fresh available ingredients. 

Dave's Pub & Grill Restaurant @ the Oakwood Resort enjoy a relaxed atmosphere whether it’s mealtime, time for an appetizer or you need a cold beverage.   


Places to Stay

Oakwood Resort Grand Bend is a higher-end experience with an 18-hole golf course, 122 rooms/suites/cottages, lakeside spa, private beach access, indoor pool/sauna and hot tub. It has two restaurants on site.  

Doone Manor-on-the-Beach is the only hotel right on the beach. It is a peaceful place to stay and is ideal for couples or families. 

Blue Water Motel: With rooms and cottages, there is something for everyone, including a large outdoor heated pool, a large firepit complete with wood, a barbeque, picnic area and kids playground.   


Windsor – Day Three

Distance to Next Stop:  213 km / 139 mi  

Welcome to the most south westerly part of Ontario! Windsor is home to one of the most beautiful waterfronts where you can see Dieppe Gardens honouring World War II veterans or walk through Windsor Sculpture Park, an outdoor art gallery featuring 31 large scale sculptures. Make sure you wear your stretchy pants for a visit to Windsor Style Pizza. For 60 years, Windsor residents have been fiercely devoted to their pizza.  Windsor also offers world-class gaming at Caesars Windsor, one of the largest casinos of its kind in Canada.   

Windsor enjoys a fascinating history of rum running and prohibition. Make sure you include a walkthrough of Walkerville distillery district to experience the “colourful” days of prohibition.   

Enjoy this culturally diverse city, the birthplace of Canadian Club Whiskey (nicknamed CC) and now home to the Dirty Poutine Tour


Things to Do

Waterfront:  Day or night, enjoy one of the most underrated waterfronts with Dieppe Gardens or walk through Windsor Sculpture Park featuring 31 large scale sculptures.  

Dieppe Gardens: Named after Dieppe, France, where the Essex Scottish Regiment comprised of 5,000 Canadian, British and American men landed. The battle resulted in 3,000 casualties.  

Jack Miner’s Bird Sanctuary: Migratory Waterfowl Refuge System.  

WindsorEats Tours: Bikes & Beers tour, Wine Trail Ride cycling tours.  

Walkerville District: Perfect blend of hip and historic! Great area in Windsor.  


Places to Eat


Toast:  Great sandwiches and breakfast classics like waffles and eggs Benedict. 

Stacks: Walk in and place your order at the front, receive your number and grab a seat!  

Twisted Apron: Where you can find comfort food served with a creative twist from brunch to burgers and salads. 


Grand Cantina: Serving up your favourite tacos, nachos, burgers, fries and churros.  

Chapter Two Brewing Company: Making quality brews in classic styles. There is usually ‘Guest’ Beer that they keep their Brewer (and customers) excited.  

Mamo Burger Bar: Serving burgers made with local beef, piled high with creative topping combinations in a casual atmosphere. 

Arcata Pizza: Its world famous pizza sauce contains a secret blend of spices that customers love.  

Mezzo Ristorante & Lounge: Great Italian food served in an upscale setting.  

Distance to Next Stop: Amherstburg 30 km / 19 mi  

Amherstburg is deemed one of the prettiest and oldest communities in Southwest Ontario, known for its gardens, beautiful views, quaint shops and 16 wineries. Amherstburg is nestled on the shores of Lake Erie and the Detroit River. 


Things to Do

Amherstburg Freedom Museum: The Amherstburg Freedom Museum tells the story of African-Canadians’ journey and contributions, by preserving stories and presenting artifacts that educate and inspire.  

Fort Malden National Historic Site: Fort stood guard during the war of 1812, a time when the threat of American invasion was very real. The Americans occupied this fort for almost two years after the British abandoned it following their defeat at the Battle of Lake Erie. 

River Book Shop: Amherstburg is located by the Detroit River. It strives to bea comforting and ever-changing entity and community hub.  


Places to Eat


Caffeine & Co.: Located in the heart of Amherstburg. Visit for a high-end coffee to fulfill your caffeine needs. The bakery is divine, complete with cakes and the most beautiful cookies and macrons.  


Wolfhead Distillery: inspired by the local history of rum running and Prohibition in the area A craftsman’s operation, Wolfhead incorporates the resources found in its own backyard in producing unique flavours. 

Artisan Grill: A premium casual dining experience. 

Riccardo’s Italian Restaurant: Weather permitting an outdoor patio with live entertainment, or indoor full dining room.  

The Salty Dog: An upscale pub located in beautiful downtown Amherstburg.


Kingsville – Day Four

Distance to Next Stop:  37 km / 23 mi  

Rich in Victorian heritage, Kingsville, “Canada’s Southernmost Town”, welcomes you with authentic experiences for foodies and wine lovers alike, alongside unique and eclectic shopping in boutiques and garden centres. Kingsville is playground for outdoor enthusiasts where stellar boating, fishing, and golf meet with miles or recreational trails and waterfront charm. Jumping off point to catch the ferry to Pelee Island. 

A man and woman walk on a boardwalk surrounded by water and tall grass


Things to Do

Ferry over to Pelee Island: The most southern point in Ontario where you can spend the day swimming, browsing through lovely shops, or indulging in food and drink.  

Dutch Boys Chocolate Shop: Unique hand carved wooden moulds become dark chocolate birds, dogs, cats, pigs, pears, etc. Cor and Henry have also created their own artisanal line of hand-crafted truffles and chocolate bars as well.  

Blimey’s British Shop: A shop filled with all kinds of goods from the UK – garments, chocolates, confectioneries, books, etc.  


Places to Eat


Beach House Grill: Great food, great prices. 


Epic Wine Route: 12 wineries and 1 EPIC passport. A tour of Windsor Essex’s wine country has so much to offer wine enthusiasts, foodies and more 

Oxley Winery: Oxley Estate Winery, in the heart of the wine route on charming County Road 50, makes small batch award winning wines and nice outdoor patio. 

Colasanti’s Restaurant: Famous “Broasted Chicken,” pizza, apple cider, hot homemade donuts and butter fudge.  

Jacks Gastro Pub: Serves up seasonal menus created with local farmers, producers and artisans. Wrap-around porch, outdoor patios and distinctive dining rooms.  

The Grove Brew House: Very hip! The hotel offers a 24-hour self-serve coffee bar – always stocked with local homemade treats and hot bevies to get you through the day. 

2 glasses filled with dark beer and 1 glass filled with amber coloured beer


Places to Stay

The Grove Hotel: The newly renovated Grove Hotel, in the heart of Kingsville boasts 18, uniquely themed rooms in the historic 1850 structure.    

Kingsville House B&B: This historical building is beautiful and close to Kingsville’s, restaurants, shops, off-road trails and Lake Erie’s shoreline. Close proximity to wineries. 

Distinctive Inns of Kingsville: With rooms for every taste and every adventure.  

The Walnut Grove B & B: Provides a spa-like setting for a memorable stay. 

Distance to Next Stop: Leamington 16 km / 10 mi  

Last but not least: Leamington. Known for its long summer, birding and beaches, it is an  outdoor adventurer’s paradise. Prepare to be captivated by Leamington’s Carolinian forests, rare and endangered species, the spectacle of annual bird and butterfly migrations at Point Pelee National Park, and Lake Erie’s famous sunsets along the sandy beaches of Seacliff Park.

The amount of produce that is grown is this area is phenomenal. Home to the largest concentration of greenhouses in North America, roadside fruit stands offer everything from apples to zucchini. Make sure you take a little local home with you!  


Things to Do 

Day use Point Pelee National Park is situated at the southern extreme of mainland Canada. Point Pelee National Park is a tiny sanctuary supporting a mosaic of habitats from jungle-like forest to lush wetlands to open savannah.  

Leamington Farmers Market: Fresh meat, fruit, fish, vegetables, baked goods, flowers and home crafts. 

Seacliff Park: Home to Leamington's tomato splash pad and an amphitheater overlooking Lake Erie. Access to a pavilion with barbecue, picnic tables and washrooms. 


Places to Eat

Pelee Trading Post: Can’t miss it as it’s a double-decker bus on the way into the Point Pelee National Park.  

Cured Craft Brewery Co.: Pizza, apps, sandwiches and desserts! 

Joey’s Seafood Restaurant: Daily specials, fish and seafood at great prices. 


Places to Stay 

Best Western Plus Leamington: Newly renovated, new fun activity atrium with a two-story play kingdom and indoor water park. 

Seacliff Inn Leamington: The historic Seacliffe Inn, dating back to the turn of the 20th century, is a nautical-themed gem. Twenty-three individually designed guest quarters offer a luxurious retreat from everyday life.  

Otentiks at Camp Henry: Point Pelee oTENTik are a unique Parks Canada accommodation providing a relaxing, comfortable and easy way to camp! A cross between an A-frame cabin and a prospector tent. 

HoriZen Bed & Breakfast: A place of calm where guests can rejuvenate.  


Things to Know

Last updated: October 31, 2023

Looking for Ontario travel advice?

Our experts are here to help you plan your perfect trip. Call or book today.