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Its tree-lined streets, abundance of sidewalk cafes and powerful connection to the water give Oakville, Ontario, a distinctive Mediterranean vibe. But there’s more to this Port of Call than just its joyous, Côte d’Azur feel.
Located on the north shore of Lake Ontario midway between Toronto and Hamilton, the beautiful community of Oakville stands as living proof that you really can have your cake and eat it too, perfectly balancing the luxurious amenities of today’s modern world with the kinder, slower and far more genteel pace of life that defined the previous century.
It’s an existence where residents eschew big box chains in favor of independent shops lining a lively main street, buying their meats from the butcher and breads from the baker, without a Costco or a Supercenter in sight. Oakville represents a living dichotomy — a forward-looking anachronism where the best of all worlds seem to thrive in perfect harmony.
If you’re looking for a unique new Port of Call to explore this year, then Oakville is the place for you.
Visitors to this charming lakeside community quickly come to appreciate why Oakville consistently polls among Canada’s most desirable communities in which to live. Its population of around 220,000 people certainly ranks among the country’s most affluent, with average home prices well into seven figures and large lakefront estates commanding $60 million or more. A Saturday morning stroll along Lakeshore Road — the main commercial street and the very heart of the community — is truly a car lover’s mecca, where familiar nameplates like Chevy and Ford share parking spaces with more exotic marques like Porsche, Aston Martin, Maserati, Lamborghini and Bentley. Oakville is home to the iconic Glen Abbey Golf Club — reportedly a favorite of Tiger Woods — along with some of the most prestigious private schools in the country, including Appleby College, MacLachlin College and the St. Mildred’s-Lightbourn School for Girls. As one might expect, that kind of wealth assures Oakville’s place among Canada’s safest communities, with the town notching the lowest crime rate in the country for 15 consecutive years. It’s also among the cleanest; litter is simply non-existent, and town employees spend most of their time not sweeping up, but tending the massive flower boxes and hanging planters that line Oakville’s principal streets.
But it isn’t just affluence and civic pride that give Oakville its Côte d’Azur feel. Like Monte Carlo, Nice and Cannes, Oakville enjoys a powerful connection to the water, and the natural harbor that provides its raison d’être.
Once upon a port
Oakville overlooks Lake Ontario at the mouth of Sixteen Mile Creek — so named because it lies precisely 16 miles from Hamilton and the same distance from Toronto. It’s easy to spot from the water, just look for Oakville’s two concrete piers — the eastern one has a flashing red light mounted atop a cylindrical white tower with a bright red cap. A green spar buoy, located about 100 yards off the end of the western pier, marks the beginning of the dredged entry channel. From here, it’s tough to miss the word “Oakville” set in large white letters on the hillside above the western pier.
The approach into the harbor is completely free of obstructions, and over a soft, sandy bottom. Water depth in the harbor is normally somewhere around eight feet, with a buoyed channel leading upstream. There are four principal marinas, with the majority of the boats appropriately moored Mediterranean style. The excellent facilities in Oakville Harbour stem from its previous life as a busy commercial port, one which did a substantial business in shipping fruit, wheat and — as its name suggests — lumber. Business flourished through the early part of the 19th century. A ship builder set up shop on the western bank of 16 Mile Creek, followed by other industries close by, including a large granary. In 1834, Oakville’s bustling harbor had reached such a level of activity and importance that it was declared an official Port of Entry into Canada.
But by the mid-1800s, Canada found itself mired in a deep recession which, in conjunction with the arrival of the railroad, led to the rapid decline of Oakville as a meaningful industrial port. Facing the prospect of economic collapse, the town began pitching itself as a holiday destination to residents of nearby Toronto and Hamilton, touting its lack of industry as a plus, bringing clean air, quiet streets and dirt-cheap land values. The plan worked, and Oakville quickly became the fashionable summer abode for dozens of Canada’s wealthiest families. Rich industrialists took advantage of the low land prices to build sprawling estates in town, as former commercial properties along the waterfront gave way to opulent residences and large hotels with expansive verandahs offering panoramic lake views. Known today as Historic Oakville, the old town was officially designated a Heritage Conservation District in 2013.
The abundance of estate lots and original period architecture in Historic Oakville has long been prized by Hollywood film producers, and the town continues to serve as a principal filming location for major films and television productions. If you should experience a sense of déjà vu when walking its stately avenues, it could well be because the surroundings are indeed familiar — at least to your television screen.
Today, Oakville’s unique charms attract more than 1.4 million tourists every year, many of whom visit specifically to enjoy its stately heritage sites. A self-guided historical walking tour leads visitors through the historic district, where scannable QR codes explain the significance of various buildings and landmarks. Of course, free public Wi-Fi — available throughout downtown Oakville — ensures a fast and reliable internet connection anywhere.
Photo Courtesy of Heart of Ontario
Photo Courtesy of Kerr Village Facebook
Photo by Craig Ritchie
While Oakville is justifiably proud of its heritage, the town’s present-day attractions provide even more reason to visit — especially with most of the goodies located within easy walking distance of the docks.
Lakeshore Road, which parallels the shoreline about two blocks from the water, and the streets immediately around it on the east side of 16 Mile Creek represent Oakville’s downtown core. Wandering here is always a delight for the senses, with a wide assortment of restaurants and their enchanting sidewalk cafes tempting visitors with a diverse variety of tastes and aromas, offering choices from burgers to pubs to fine dining, with menu options ranging from steaks to seafood to Mediterranean, Japanese and Middle Eastern fare. Dining alfresco is very much the Oakville way, whether it’s that first morning coffee and croissant, or a splurge dinner at one of the town’s more than 200 restaurants.
If you prefer to provision and cook your own masterpiece back on the boat, you’ll find downtown Oakville offers a shopping experience second to none. Here you’ll find independent butchers, bakers, grocers, fishmongers, pastry shops and dessert stops — many of which have been there for generations — providing everything needed to restock the boat’s galley. You’ll never touch a grocery cart, but you will come away with exquisite ingredients for truly memorable meals, and an experience like no other.
If your appetite leans more toward shameless self-indulgence, then you’ll certainly feel right at home with a selection of luxurious spas to explore. Book a massage, enjoy hot stone therapy, kick back with a pedicure or simply relax and allow your cares to float away as you leisurely ponder activities for the evening and the coming day.
Because no port visit is complete without a little retail therapy, be sure to take time to wander Oakville’s mind-boggling array of specialty shops scattered throughout the downtown, presenting all manner of goods and curiosities from hand-made fashions to sustainable housewares to original art. And if you’re shy of space on the boat, fear not — most shops will be more than happy to ship your new treasures home, or anywhere in the world.
If you’re in the mood to be entertained, then only steps from the docks you’ll find the Oakville Centre for the Performing Arts, which presents more than 250 performances of music, drama, comedy and dance each year. Opened in 1977, the Centre comprises a 470-seat auditorium and a 120-seat studio theater for more intimate presentations.
There’s no shortage of outdoor entertainment throughout the summer, as the town hosts a wide variety of festivals and special events, including the Oakville Family Ribfest, the Film Festival, the Oakville Jazz Festival, the Summer Concert Series, Kerrfest, the For The Love of Arts Festival and more. For up-to-date information on what’s going on through the season, check Oakville’s comprehensive online events calendar (visitoakville.com/events).
There are further shopping and dining opportunities on the west bank of 16 Mile Creek as well, and particularly as you walk north of Lakeshore on Kerr Street into the heart of Kerr Village. There you’ll find an eclectic mix of retail, coffee shops, bakeries, bistros and more, all with a distinctly funky vibe. Once again sidewalk cafes abound, inviting a stop to refresh and relax while planning one’s next adventure.
Stretch those legs
As much fun as it is to simply wander the magnificent, tree-lined streets of downtown Oakville, stopping here for a snack and there for a browse, Oakville is an active community with no shortage of opportunities to really stretch one’s legs. If you have bikes onboard the boat, here’s your chance to put them to use. Continuing east on Lakeshore beyond the historic downtown leads into an enchanting residential neighborhood where exquisite homes with stately, manicured lawns are nestled between the oak groves. The area — known as the Gold Coast — is home to some of Canada’s most expensive and exclusive real estate, with one eye-popping mansion after another. This includes Chelster Hall, a 47,000 square-foot palatial estate situated on 10 acres of waterfront heaven. Sheltered behind a gatehouse and two sets of iron gates, the estate even includes its own private chapel.
Pedal long enough and you’ll come to Gairloch Gardens, home of the Oakville Galleries, a not-for-profit art museum overlooking Lake Ontario. Its extensive permanent collection of paintings, drawings, sculpture and mixed media focuses on the work of prominent Canadian artists, and is considered among the finest of its kind.
Oakville is a city of parks, and you’ll spot plenty of them as you wander about. Erchless Park, located on the east side of 16 Mile Creek just above the piers, is what remains of the once 960-acre Erchless Estate, home to the Chisholm family, Oakville’s original landowner. Today, the house operates as the Oakville Museum, presenting a diverse collection of objects reflecting the history of the town from its establishment to the present day, including costumes and textiles, fine and decorative arts, ethnological artifacts and Chisholm family related materials.
If you’re looking to have some fun on the water instead of on the bikes, then this is the spot to break out the dinghy, the kayaks or a stand-up paddleboard. The serene waters of 16 Mile Creek provide a well-protected playground for paddling, particularly as you venture farther and farther upstream, past the Oakville Powerboat Club at Hillmer Park, and leave the houses behind. A silent approach allows the opportunity to spot a variety of wildlife including raccoons, beavers and red foxes, along with a wide range of birds, from tiny hummingbirds to great blue herons and the occasional bald eagle.
When paddling about in the deeper water near the harbor, or in Lake Ontario proper, keep an eye out for fast-moving watercraft. Oakville is home to the Burloak Canoe Club, a popular competitive rowing group that can count no less than three Olympians — Adam van Koeverden, Mark Oldershaw and Larry Cain — among its members.
Fishing is also popular among local boaters. The clear waters right off the Oakville waterfront provide good action with smallmouth bass and walleye right through the summer. But things really get festive from August through October as coho salmon, Chinook salmon, brown trout and steelhead return to the waters off Oakville in anticipation of their fall migration up 16 Mile Creek to spawn. The Great Ontario Salmon Derby — one of Ontario’s most popular fishing contests — offers participants the chance to take home all sorts of prizes from tackle to trucks, attracting anglers from across the region each year. The derby, which celebrated its 25th anniversary in 2022, is a beloved local institution, and it’s hard to not get caught up in the excitement, even if you’re only in town for a few days. A substantial local charter fleet makes it easy to join in the fun, providing all the gear and know-how so you can focus on reeling in the catch.
Really, what more could a person want?
With its first-rate marina facilities, and its extraordinary shopping, dining and entertainment options all just steps from the docks, Oakville offers visiting boaters the best of both worlds: Thoroughly modern amenities and conveniences, set in a beautiful location that hasn’t outgrown the peaceful and genteel pace of life that defined the previous century.
Looking for an endearing Port of Call to visit this year? Point your bow to Canada’s Côte d’Azur, and you’ll fall in love with it too.