LOCAL HISTORY REVEALED

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.

Tannery and Waterworks Parks are adjacent green spaces to 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.

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.

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 just 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 Queen Elizabeth Park Community and Cultural Centre is a cultural hub worth checking out – hosting public art exhibitions, events, workshops and more, including a number of Ontario Culture Days events.

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.)

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.’

INSPIRED BY NATURE, CREATED FOR PERFORMANCE

Bright and airy, the FirstOntario Arts Centre Milton is an interdisciplinary arts venue that hosts a wide range of performances. Enjoy an evening of live music – from folk to the local Philharmonic – or take in a lively lecture series, film forum, or hands-on workshop.

The venue itself is inspired by Milton’s natural surroundings, with limestone, wood finishes and glass reflecting themes of water, agriculture, and the escarpment. If you’re intrigued by the design, consider booking a behind-the-scenes tour to learn more and to get a peek at the stage, green room and the Holcim Gallery with its visual arts exhibitions.

A WORLD OF GREEN SPACES

You’d be hard-pressed to pick just one conservation area to visit near Milton. The region is home to half a dozen gorgeous spots, where you can hike, bike, rock climb, ski, golf and more. First, fuel up at the aptly named Trail Eatery in Campbellville. Then, noting that reservations are required to visit some conservation areas, you’re spoiled for choice. Crawford Lake Conservation Area features a stroller-friendly boardwalk dotted with wood carvings, as well as cross-country ski and snowshoe trails. It’s also home to the Longhouse Village, with three reconstructed fifteenth-century longhouses and the Three Sisters and Mashkiki Gitigan (medicine garden), a window into Indigenous agriculture and the lives of the meromictic lake’s original residents.

RIDE THE RAILS

It all began in 1954 with a Toronto Transit Commission streetcar saved from the scrap yard by a group of devoted railcar fans. Today, adults and kids alike enjoy Ontario’s largest electric railway museum with its historic railcars that operate on two kilometers of scenic track. The museum has an impressive collection as well, featuring vintage streetcars, locomotives, and buses, many of which you can explore inside. Plus, the museum houses various other rail-related paraphernalia. No wonder it’s also been featured as a backdrop for film and TV productions, including Anne of Green Gables — it’s a sweet spot. It’s open seasonally, so check ahead.

THE RURAL URBAN CONNECTION

Country Heritage Park makes the connection between rural and urban, farming and food. It’s home to some beautiful 19th century buildings, including a church, a townhall and a schoolhouse. The park runs events of all kinds from craft fairs to truck pulls, as well as selling farm-fresh products. Make time to visit the garden created in conjunction with Grandmother’s Voice (an organization dedicated to sharing the wisdom of Indigenous grandmothers, elders and knowledge holders). The healing garden can be entered from all four directions and holds over thirty species of native plants.

FROM SOUTH ASIAN TO STEAKHOUSE

Milton’s dining choices include some very tasty South Asian cuisine — no surprise given South Asian residents represent close to thirty per cent of the town’s population. Options include buffet style at Bombay Grill, Pakistani dishes at Spice Fusion and naan at Naan Guys. There’s also fine dining of many cultures to be found, including gourmet Indian cuisine at Chef Sanjeev Kapoor’s Khazana and Italian at Pasqualino (cooking classes also on offer). Feel more like pubbing? For a small city, Milton is replete with pubs, including the Ivy Arms, Rad Brothers Sports Bar & Tap House, Ned Devine’s Irish Pub and Bryden’s Pub & Restaurant. Ask for a local craft beer made by Orange Snail or Third Moon – or simply head straight to the breweries themselves to taste the brews in their original habitat.

A PAINTED CITY

Hamilton has rightfully been called a city of murals, and you’ll see the vibrant public art form everywhere, including James Street North, Burlington, and Mary streets, and features a significant amount of eye-catching work by sought-after Haudenosaunee artist, Kyle Joedicke. Cyclists may choose to explore the one-hundred-plus murals on two wheels, thanks to the Hamilton Bike Share’s “Everyone Rides” initiative Mural Map. And July’s Concrete Canvas Art Festival gives one and all a chance to watch mural artists in the act of creation. Next on your plate could be some excellent dining, since Hamilton’s growing reputation as a creative culinary hotspot makes for many possibilities. To name a few: Mexican cuisine at The Mule, Italian at Born and Raised (home to Top Chef Canada finalist Vittorio Colacitti), pub food at Odds Bar (founded by two members of the band Arkells) and vegan cuisine at Democracy*.

FROM PUNK TO JAZZ TO CLASSICAL

Seems like every few years there’s another article about Hamilton’s music scene blowing up. Not a surprise, given the city is the birthplace of bands like Arkells, Whitehorse and Monster Truck, and home to Daniel Lanois’ world-renowned Grant Avenue Studio. There’s even a TV show (“This Is The Thing”), based on fictional Hamilton musicians — showcasing actual Hamilton musicians and comedians. In September, James Street’s Art Crawl turns into Supercrawl, celebrating music alongside art. Plus, the ongoing scene runs the gamut from punk to jazz to classical. FirstOntario Concert Hall is home to the Hamilton Philharmonic Orchestra as well as presenting a range of concerts by touring artists. Mills Hardware is a cool live music space with a long history: acts like Ronnie Hawkins and The Hawks, The Ink Spots, The Tragically Hip and The Ramones have all played at the venue. Today, the programming crisscrosses music genres along with theatre, comedy and more. As for the thriving local scene, check out the beloved Casbah Lounge.

THE VALLEY TOWN

Stop in lovely little Dundas on your way back downtown. The “Valley Town,” as Dundas is known, is a true sweet spot: its historic 19th-century centre is dotted with boutiques and cafés and surrounded by green space. (Not to mention it has the distinction of hosting the annual Cactus Festival, which has led some to call Dundas the “cactus capital of the universe.”) Dundas also has a thriving visual arts scene, with the Dundas Valley School of Art, Millworks Creative’s community of artists, and a bustling annual studio tour each fall. Permanent galleries include The Carnegie Gallery, with exhibitions by contemporary Canadian artists (and arts and crafts by locals on offer), plus Danuta Niton — Art of Design Studio, and Lorraine Roy Art Textiles.

COOL, GRITTY…AND CHARMING

From cotton mill to creative hub, welcome to The Cotton Factory. Back in 1900, Hamilton was on the verge of an economic boom that made its steel famous, but textiles played their part too, notably the Imperial Cotton Company’s canvas manufacturing. Today, the charming old building has been repurposed as a centre for artists of all kinds (furniture designers, photographers, musicians, filmmakers etc.) to create and collaborate. Art experiences, markets and open studio days are regular features, with some studios selling the work of local makers. Located in a cool, gritty, and evolving part of Hamilton you’ll also find interesting spots to dine not far away. For instance, Motel Restaurant’s hipster brunches, Mosaic (“a chill bar with a warm vibe”), the Galley Pump’s hometown comfort food, and O Leão Cafe & Restaurant’s Portuguese cuisine.

STAGE AND SCREEN

Theatre Aquarius is known for producing high-quality work and for its interest in bringing new plays to the stage. In other words, the name Theatre Aquarius is synonymous with accessible, challenging, and entertaining live theatre. But it also serves as a vibrant part of Hamilton’s arts community through theatre arts education for young people of diverse backgrounds, and with Indigenous, newcomers, and LGBTQ+ outreach programs. Note too that Hamilton offers a theatre experience of the filmic kind at the Playhouse Cinema, where you can enjoy all manner of movies in a restored and beautiful theatre dating back 105 years.