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