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Road Trip Trifecta: Windsor, Chatham-Kent and Sarnia
Road Trip Trifecta: Windsor, Chatham-Kent and Sarnia
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Road Trip Trifecta: Windsor, Chatham-Kent and Sarnia

By Shannae Ingleton Smith (@torontoshay)

The southern tip of our region offers world-class beaches, some of the continent’s best birding, a rapidly evolving wine and culinary scene and the friendliest communities on the planet.

On a recent girls’ trip, we hit the road for a three-day exploration of Windsor, Chatham-Kent and Sarnia.


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Windsor, Ontario


Four hours’ drive southwest of Toronto, the city of Windsor turned out to be a pleasant surprise. I had been to a neighbouring town a few times to visit family, but had never explored Windsor.

The southernmost city in Canada is rich with history — most notably, it was once a major entry point for Freedom Seekers using the Underground Railroad, a secret network of people who helped African-Americans escape enslavement to the free northern states and to Canada.

The city is also known for fuelling the alcohol industry during the days of Prohibition. Between 1920 and 1933, 75 per cent of the liquor that made its way into the U.S. came through the Windsor-Detroit "Funnel."

A tour of the famous J.P. Wiser’s Distillery is a must-do; after learning all about the history and craftsmanship behind Canadian whisky, Lily and I capped it off with a complimentary whisky tasting.

J.P. Wiser’s Distillery Experiencer, Windsor ONJ.P. Wiser’s Distillery Experience, Windsor ON
J.P. Wiser’s Distillery Experiencer, Windsor ON

From there, it was off to Willistead Manor, an opulent and historic site perfect for weddings and special events. Built in 1906, the mansion has an unbelievable 36 rooms that would put any MTV Cribs episode to shame.

After exploring the legendary landmark, we checked in at Caesars Windsor Hotel, home to a casino that runs 24/7 and one of the biggest in the area. While Lady Luck was not our friend, we hit the jackpot with the accommodations, from the luxurious and immaculate suites, to the spa, pool, restaurants and other amenities.

Caesars Windsor Hotel, Windsor ON Caesars Windsor Hotel, Windsor ON
Caesars Windsor Hotel, Windsor ON

Windsor also boasts a vibrant bar and restaurant scene, and after all the site-hopping, a girl has got to eat! At The Twisted Apron, a delicious comfort food restaurant, our brunch consisted of French Toast, Eggs Benedict, mouth-watering Mac & Cheese and a delightful selection of homemade jams.

The Twisted Apron, Windsor ONThe Twisted Apron, Windsor ON
The Twisted Apron, Windsor ON

For dinner, the award-winning Neros Steakhouse at Caesars Windsor offered sumptuous steak and lobster, as well as an impressive wine list — I recommend the white sangria!

After dinner — since it was a girls’ trip and the night was young — we headed to Wineology Bar & Restaurant, located in the heart of the trendy Olde Walkerville neigbourhood, for an after-dinner drink, and then on to nearby F&B, a cozy cocktail and small plates resto, for dessert.

Both spots have Instagram-worthy statement walls. My fave was the towering wine rack on the wine cellar wall at Wineology.

Neros Steakhouse at the Caesars Windsor, ONNeros Steakhouse, Windsor ON
Wineology Wine Bar and Restaurant, Windsor ONWineology Wine Bar and Restaurant, Windsor ON

The most memorable meal, however, was breakfast the following morning at A Dog’s Breakfast, where we both ordered the Lasagna French Toast — and yes, it was as sinfully delicious and decadent as it sounds.

The Art Gallery of Windsor (AGW), the city’s cultural jewel in the crown, is another must-visit. A showcase for local, regional and national artists, this summer’s exhibits include “401 West! Portrait of the Region,” featuring painting, photography, sculptor and graphic art by 20 artists, including photography guru Yousuf Karsh.


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Chatham-Kent, Ontario


Day 2 took us to Chatham-Kent, where we visited three important historic attractions: the Buxton National Historic Site & Museum, the Chatham-Kent Black Historical Society’s Black Mecca Museum, and Uncle Tom’s Cabin Historical Site.

The Chatham-Kent region was home to many thriving Black communities and was considered the last stop to freedom for fugitive slaves fleeing the U.S. through The Underground Railway, which ferried 30,000 to 40,000 fugitive slaves to Canada.

These Freedom Seekers settled in the Chatham-Kent area where they built schools, churches and successful businesses of their own.

Buxton National Historic Site & Museum, Chatham-Kent ONBuxton National Historic Site & Museum, Chatham-Kent ON
Buxton National Historic Site & Museum, Chatham-Kent ON

During our tour at Buxton, Shannon Price, our wonderful guide and, herself, a descendant of these early Black settlers, told us about Canadian Black history, pointing out that Canada actually had its own slave trade though on a much smaller scale than the U.S.

It was informative but emotional, as we walked the same grounds as the slaves would have and observed poignant artifacts, such as tiny ankle shackles meant for children.

Black historical museum, Chatham-Kent, ONBlack historical museum, Chatham-Kent, ON
Uncle Tom’s Cabin Historic Site, Chatham-Kent, ONUncle Tom’s Cabin Historic Site, Chatham-Kent, ON

At the Chatham-Kent Black Historical Society’s Black Mecca Museum in Chatham’s east end, we learned the stories of Black people who lived in this growing hub during the 1850s and 1860s, such as Mary Ann Shadd Cary, who founded the anti-slavery newspaper, Provincial Freeman, making her the first woman publisher in North America.

Less than a half-hour drive north, near Dresden, Ont., we visited the famous Uncle Tom’s Cabin Historic site, a five-acre, open-air museum of interpretive videos, exhibits and artifacts dedicated to Josiah Henson, a fugitive slave and abolitionist. Henson served as the model and inspiration for Harriet Beecher Stowe’s groundbreaking book Uncle Tom’s Cabin, published in 1852.

We came away with a renewed respect for the resilience and innovation of these brave people who risked their lives crossing the border to freedom.

After the historic-site touring, we checked into RetroSuites, a luxury boutique hotel in Chatham where every room has its own personality — ours was Paris-themed with quaint, Parisian décor.

RetroSuites, luxury boutique hotel in Chatham, ONRetroSuites, luxury boutique hotel in Chatham, ON
RetroSuites, luxury boutique hotel in Chatham, ON

For food and drink, we opted for Portuguese cuisine at Chatham’s Breakfast House & Grille Churrascaria, and fish and chips with seafood at the Bayside Brewing Company, located in the scenic village of Erieau.

Aside from the deliciously fresh food and local craft beer, local musicians gather on the restaurant patio to jam every Sunday.

Bayside Brewing company, Chatham-Kent, ONBayside Brewing company, Chatham-Kent, ON
Chilled Cork,Chatham-Kent, ON Chilled Cork, Chatham-Kent, ON

When planning your trip, build in some time to explore this area and the warm waters of Lake Erie. It’s the perfect spot for wakeboarding, windsurfing, fishing, sailing or just lazing about on the beach.

Before leaving Chatham-Kent the next morning, we stopped at The Chilled Cork for another French Toast fix. The Strawberry Chocolate French Toast was the stuff of dreams; you could say I’m obsessed!


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Sarnia, Ontario


The last leg of our trip on Day 3 brought us to Sarnia, one of Ontario’s busiest marina centres, where boating and water activities are a tempting tourism attraction.

When the clear blue waters of Lake Huron beckon, you can take a cruise, scuba dive, surf or sail — and of course swim at some of the province’s cleanest and most beautiful beaches. It’s all within easy reach in this water playground.

We spent a relaxing day at the Bridgeview Marina, sailing the St. Clair River in style on the Palm Breeze III, a 42-foot Sea Ray. The marina, first established in the 1960s, has easy access to the river and Lake Huron and is one of largest full serviced marinas in the Great Lakes.

Bridgeview Marina, sailing the St. Clair River in style on the Palm Breeze III, Sarnia ONBridgeview Marina, sailing the St. Clair River in style on the Palm Breeze III, Sarnia ON

From there, we browsed the cool merch at Urban Escape, a retailer hybrid of Club Monaco and Restoration Hardware. This unique shopping experience blends furniture, home décor and fashion that’s the stuff of a lifestyle blogger’s dream — Lily and I were on cloud nine!

We then hit Lola’s Lounge for dinner where the funky aesthetic and vibe complemented the food to perfection. Look out for seasonal fish dishes, including perch from the local Purdy’s Fish Market.

Lola's, Sarnia ONLola's, Sarnia ON
UrbanEscape Inc., Sarnia ONUrbanEscape Inc., Sarnia ON

To top off the night, we grabbed another quick bite and drinks at the Refined Fool, a local microbrewery started by a group of local home brewers from all walks of life, including teachers, musicians, entrepreneurs and pastors!

Sample a few cold ones from the robust menu, featuring inventive names like “Wowsers,” “Pinky Brewster,” “My Cousin Knows the Drummer” and “Canatara,” named after the popular, 100-acre Canatara Beach and Park.

Located just north of Highway 402, the park covers 3,000 feet of Lake Huron shoreline and offers a variety of amenities, including an animal farm and train for kids, picnic areas and bike rentals.

Before we left Sarnia, we stopped in at the Judith and Norman Alix Art Gallery to see “Photography in Canada 1960-2000.” Organized by the Canadian Photography Institute of the National Gallery, the exhibit features nearly 100 photographs by 71 artists, including Jeff Wall, Michael Snow, Ed Burtynski and Diana Thorneycroft who will be giving a talk August 8.

Refined Fool Brewing Co., Sarnia ONRefined Fool Brewing Co., Sarnia ON
Refined Fool Brewing Co., Sarnia ON

From eats and drinks, to cultural sites and tourist attractions rife with rich Canadian history, this was a girls’ trip for the books.

Planning your next vacation, visit Ontario's Southwest for trip ideas and travel deals.

This content was produced by The Globe and Mail's Globe Content Studio.
The Globe's editorial department was not involved in its creation.

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