Dark haired person stands in front of large wall mounted typewriter keys Photo courtesy of Oakville Museum

Oakville

Oakville’s gracious lakeside charm makes it one of Ontario’s most sought-after spots to call home. At an easy 30 kilometres from Toronto, it’s an ideal destination for visitors too – both for its waterfront beauty and its history as an industrial port and stop along the Underground Railroad. Located on the treaty lands and territory of the Mississaugas of the Credit First Nation, you may notice treaty lands signs as you wander, all part of Debwewin: the Oakville Truth Project, aimed at recognizing the area’s Indigenous past.

Day One

Morning
DOWNTOWN AND KERR VILLAGE
CHARMING AND ECLECTIC

The quaint charm of a small town with an eclectic range of shops creates a downtown Oakville atmosphere that beckons one to linger. Your only challenge will be which cafés to include in that quest! Some local favourites are Croissant Express Bakery (known for amazing croissants) and the cozy Tribeca Coffee Company. Or you could detour to eclectic Kerr Village, a pebble’s throw from the lake and home to the popular Vereda Central Coffee Roasters (where coffee is a “delicious science”). Brunch lovers note: Kerr Street Café and Stoney’s Bread Company are beloved for their brunches.

The Oakville BIA’s signature events, including Hometown Holiday and Taste of Oakville, along with their street sales and local gatherings, cultivate a strong neighbourhood spirit. Upscale fashion shopping is also a big thing in Oakville, from European-sourced styles at Must Boutique to beautiful, affordable clothing at Luxfindz and Second Chance’s consignment discoveries, along with antiques and artworks at Turner Chapel Antiques. Shopping for art is a thing too, with many private galleries. To discover the works of emerging and established artists, visit Towne Square Gallery or Summer and Grace Gallery, and for contemporary art, Prometheus Art Gallery. When in Kerr Village don’t miss Rumi Galleries, where you’ll find modern art by British and North American masters.

Afternoon
Oakville Museum; Tannery and Waterworks Parks
LOCAL HISTORY MEETS CONTEMPORARY ART

Another prominent historical estate-turned-museum in Oakville is Erchless Estate, one-time home of Oakville’s founding family, the Chisholms. The main house, Erchless (pronounced “erkless,” meaning “by the stream” in Scottish Gaelic), is where the museum resides. Among other things, it is notable for two permanent exhibitions devoted to Oakville’s Black history: “Freedom, Opportunity and Family,” sharing the stories of African-American families who made Oakville home, and the multimedia exhibit “The Underground Railroad — Next Stop Freedom!” narrated by the ghost of Deborah Brown telling the true story of her flight from slavery. The estate is also home to Oakville’s Old Post Office Museum, built in 1835, and in the summer, you can take a tour and try your hand at postal-related fun like writing with a quill pen.

Oakville Galleries is a contemporary art museum located in two spaces: downtown in Centennial Square and the other in serene Gairlockh Gardens on the lake. Oakville Galleries is one of Canada’s leading art institutions, presenting rotating exhibitions throughout the year by emerging and established artists from across Canada and around the world.

Tannery and Waterworks Parks are adjacent green spaces where you can stroll and enjoy fabulous views of Lake Ontario from the observation deck. In Tannery, you may notice a stone gathering circle decorated with images of moccasins. It’s part of the Moccasin Identifier project, an outdoor classroom providing school children with a chance to learn about the area’s rich Indigenous history. All ages have the opportunity to learn at the First Nations History Wall, located along the park’s shore.

Evening
Oakville Centre for the Performing Arts
EXCEPTIONAL DINING AND ENTERTAINING PERFORMANCES

Oakville has been called “foodie harbour” with good reason — there’s no shortage of dining options both downtown and in Kerr Village. Popular spots are Maro’s Bistro, for “reimagined” Mediterranean food; Community Restaurant for plant-based cuisine; Hexagon (listed among Canada’s 100 Best Restaurants) for stylish French food; and The Mermaid and the Oyster for seafood.

For a post-dinner treat, check out the Oakville Centre for the Performing Arts, known for presenting a variety of performances from dance to circus arts to storytelling to concerts. Its snappy slogan, “small theatre big names,” is accurate — over the course of a year, the centre presents 70 plus professional performances. But there are also hundreds of shows by local performers, making the centre a vital part of Oakville’s cultural community.

Day Two

Morning
Bronte Village, Coronation and Bronte Heritage Waterfront Parks, and Queen Elizabeth Park Community and Cultural Centre
SHAPED BY WATER

Bronte Village, like its neighbour, old Oakville, is shaped by water. For centuries, Indigenous inhabitants turned to the creeks and lake for travel and nourishment. Settlers built a busy port that saw shipbuilding, fishing and stonehooking industries — stonehooking being the tough work of gathering stone slabs from shallow waters for construction. By the mid-twentieth century, Bronte Harbour was best known for its recreational pleasures, as is true today. Consider a free walking tour via the Bronte Historical Society and visit the society’s home in the 19th-century Sovereign House to learn more. Fishing folk note: you can still angle at both Bronte and Sixteen Mile Creeks or take charters in the harbour.

Bronte is also a perfect place to slow down, perhaps with a picnic at family-oriented Coronation Park with its play areas and long beach. Bronte Heritage Waterfront Park is another spot to laze, with a wonderful vantage for admiring the harbour. Or get active by partaking in some of the many cultural events in the park — from birding lessons to bucket drumming workshops. And take a moment at the Bronte Commercial Fishermen’s Memorial, honouring those who set out in all kinds of weather to bring fish to markets from Toronto to New York City.

Nearby is Queen Elizabeth Park Community and Cultural Centre, a cultural hub worth checking out. A vibrant, multi-use public space, the building features an aquatic centre, community kitchen, two gymnasiums, a youth centre, an older adult centre, dance studios, a recording studio, fine arts studios, a digital studio, performances in the Black Box Studio Theatre and rehearsal hall, and exhibition spaces. During your visit, take in artwork by local artists in the corridors and main gallery, performances and workshops, and many Ontario Culture Days events.

Afternoon
Lion’s Valley Park and Joshua Creek Heritage Centre
GO NORTH

People love being by the lake, understandably. But don’t miss out on North Oakville as it too has much to offer — for instance Lion’s Valley Park, terrific for hiking and cycling (and gorgeous in autumn). Follow the Moccasin Trail to learn about the land from an Indigenous viewpoint as signs along the trail share stories relating to land, water and sky.

A 15-minute drive north brings you to the artist-run Joshua Creek Heritage Art Centre, a gallery ensconced in an 1827 barn amidst lovely gardens. The centre hosts arts programs and exhibits and prides itself on being something of a sanctuary from busy urban life. One way of exploring the sanctuary is by walking a labyrinth made of prairie grasses, bringing together the centre’s three pillars: art, wellness, and conservation. (Make sure to book labyrinth walks in advance.)

Many people mingling in a lobby Oakville Film Festival at Film.ca. Photo courtesy of Film.ca.
Evening
Film.ca and 5 Drive-in
DINNER AND A MOVIE

Why not make Bronte Village your stop for a leisurely dinner? A few choice spots include Por Vida Mezcal and Mexican, celebrating Mexican food and culture (and Mezcal!), The Bronte Boathouse with lake views, and Bronte’s Fish and Chips, serving customers for fifty years. Next, take a short drive to Film.ca Cinema, home to new movies at low prices. Film.ca Cinema is also the primary venue for the annual Oakville Festivals of Film and Art and runs classes for budding young filmmakers through the Film.ca Academy — making it another Oakville cultural institution. Or, cap off the evening with some retro-style entertainment at the 5 Drive-In Theatre, where you can ‘jump in your car and come as you are.’

Your trip at a glance

This guide represents a weekend-long experience, highlighting one of the many wonderful destinations in the area. To suggest a destination for a future guide, please CONTACT US.

All editorial decisions were made at the sole discretion of Ontario Culture Days staff. This guide was written by Li Robbins.