Photo: Huntsville Main Street by Bryan Dearsley / LuxuryOntario
Updated July 15, 2024 / Commissions may be earned from LuxuryOntario’s affiliate partner links
If you’re looking for a quaint and quiet small town to explore that suits your travel habits and individual preferences, you’re in luck. Whether you’re a lover of the arts and a fan of the great outdoors or are maybe a history hound who enjoys a waterfront vibe, the best small towns in Ontario deliver no end-of-fun experiences.
Though often overshadowed by the allure of larger places to visit like Toronto and Ottawa, these smaller locales have their own unique appeal that sets them apart.
From the lakeside tranquillity of Cobourg and Goderich to the cultural overtones of Stratford, from the Mennonite roots of St Jacobs to the picture-worthy island scenery of Gananoque, these towns offer fun things to do that resonate deeply with those seeking a blend of relaxation and adventure, topped off with a touch of luxury.
Whether you’re an intrepid traveller, a history buff, or simply looking for a fun day trip or weekend escape, read through our list of the best small towns in Ontario for ideas and inspiration.
The Best Small Towns in Ontario
Niagara-on-the-Lake
Situated at the confluence of the Niagara River and Lake Ontario, Niagara-on-the-Lake is a captivating town known for its colonial architecture, its lush vineyards, and a very vibrant arts scene. A juxtaposition of history and modern elegance, NOTL, as those in the know call it, will provide you with an experience steeped in charm… and sophistication.
You simply can’t talk about NOTL without highlighting its significance in the world of winemaking. The town is the epicentre of Ontario’s wine country, boasting some of the region’s most acclaimed vineyards. The unique microclimate and fertile soils create ideal conditions for producing world-class wines, particularly its celebrated ice wines. A visit here is incomplete without indulging in wine tours and tastings. Better still, book a meal at one of the best NOTL winery restaurants.
There’s plenty of history here, too. NOTL played a pivotal role during the War of 1812, and you can learn a lot about this tumultuous period at the iconic Fort George. The town’s beautifully preserved architecture is certainly photogenic, with elegant Georgian and Victorian homes lining interspersed with quaint boutique shops and excellent eateries.
The Shaw Festival, named after playwright George Bernard Shaw, is another feather in NOTL’s cultural cap. As one of Canada‘s major theatre festivals, it attracts talent from across the world, presenting a diverse repertoire of plays from April to October. NOTL’s proximity to Niagara Falls, just a short drive away, is another plus and makes it a great base from which to explore the rest of this lovely region.
Looking to enjoy a luxurious overnight stay (or two) in NOTL? Check out these stories about the best places to stay in the area:
Discover the Best Unique & Boutique Hotels in Niagara-on-the-Lake
The Best Luxury Hotels in Niagara-on-the-Lake
Stratford
Located along the banks of the Avon River, Stratford, Ontario – like its namesake in England – has become synonymous with theatre, arts… and elegance. Drawing visitors from across the globe, Stratford has in fact emerged as a premier cultural destination in Canada.
The crown jewel of Stratford is undoubtedly the Stratford Festival. Founded in 1953, it’s one of North America’s most celebrated theatre festivals and has welcomed some of the world’s top talent, presenting both classic and contemporary works but with a special emphasis on Shakespearean plays.
Beyond the theatre, Stratford’s Victorian streetscape is a delight for history buffs and architecture enthusiasts with countless things to do and explore. The town’s beautiful parks and gardens are also fun to explore. My favourite, the Shakespearean gardens, are inspired by the great Bard’s plays and are a tranquil retreat in which to relax and unwind.
Gastronomy in Stratford is another arena of exploration, boasting a diverse array of great local eateries, cafes, and gourmet shops. The annual Stratford Chefs School, along with various food festivals, showcases the rich produce of the region and the creativity of its chefs. To make it a truly memorable experience, consider checking into one of Stratford’s excellent luxury hotels.
Elora
A picturesque small town with a village feel, Elora is located in Wellington County and has plenty of fun things to do if you’re seeking a country escape. Set against the dramatic backdrop of the Elora Gorge, this quaint town is a fun fusion of historic charm, artistic spirit, and outdoor adventure.
The gorge is the town’s top attraction and draws nature enthusiasts and thrill-seekers alike. The Grand River flows through this limestone canyon, creating spectacular vistas and offering plenty of recreational activities. Whether it’s tubing down the river, hiking along the gorge’s trails, or even getting in some glamping under the stars, the gorge promises an immersive experience with nature.
The town’s historic center with its 19th-century limestone architecture exudes an old-world charm and is certainly a lot of fun to explore. Here, the streets are lined with boutique shops, art galleries, and eateries, while the Elora Mill, once a historic gristmill and now one of Ontario’s best luxury inns, blends its rich past with contemporary elegance.
A popular hub for the arts, Elora hosts various events throughout the year, such as the Elora Festival, which showcases a medley of musical performances. The town’s artistic community also contributes significantly to its cultural fabric.
Port Hope
Undoubtedly one of the best small towns in Ontario, I’m particularly fond of Port Hope for its long-time connection to the late great Farley Mowat. One of Canada’s all-time great writers, I had the great pleasure of interviewing the author of such books as Never Cry Wolf and No Birds Sang twice at his home in Port Carling, and on both occasions spent time afterwards enjoying a stroll along its pretty main street.
In fact, the townsfolk’s commitment to heritage conservation is one of the defining features of Port Hope. Strolling through its downtown area is like stepping into a living museum, where stunning 19th-century architecture, such as the ornate facades of Walton Street to the Capitol Theatre, one of Canada’s last remaining atmospheric theatres, greets you at every step.
Beyond its architectural treasures, Port Hope’s charm is only heightened by the Ganaraska River which meanders through the town. The river not only offers recreational activities such as fishing and canoeing, but it’s also where you can enjoy the annual spring spectacle of salmon and trout migration.
Various events, festivals, and fairs dot its calendar, celebrating everything from music and arts to local crafts and gastronomy. The town’s galleries, studios, and theatres are also worth checking out, too, as are the many fine places to stay in Port Hope.
Collingwood
Its position between the sparkling shores of Georgian Bay and the ski slopes of The Blue Mountains makes Collingwood an ideal place for a weekend getaway. Historically a shipbuilding hub, today’s Collingwood offers a unique mix of indoor- and outdoor fun.
Collingwood’s harbour area, once the heart of its shipbuilding industry, now offers opportunities for boating, fishing, and paddleboarding while in the distance the iconic Collingwood Lighthouse stands sentinel, watching over the boat traffic coming and going.
Culturally, Collingwood pulses with life. The town’s streets are lined with historic buildings that house art galleries, theatres, and boutique fashion stores. Annual events, such as the Collingwood Arts and Music Festival, celebrate the town’s rich artistic heritage and foster community engagement.
One of the most defining features of Collingwood is its proximity to the renowned Blue Mountain Village and ski resort. During winter, the town becomes a bustling hub for snow enthusiasts as the slopes at “Blue” welcome skiers and snowboarders from near and far. Beyond skiing, The Blue Mountains offer other year-round attractions including mountain biking and hiking trails in the summer to panoramic gondola rides showcasing breathtaking vistas.
If you can, do as I do and spend at least one or two nights at one of the better hotels in Collingwood. To find out more about the best, check out this great content from LuxuryCollingwood.com:
Classy Digs: The Best Luxury Hotels in Collingwood
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Cobourg
Situated on the northern shores of Lake Ontario, Cobourg seems to seamlessly meld its rich history with the beauty of its lakeside setting. Referred to as the “Gem of Lake Ontario” by savvy marketers, Cobourg is certainly another of the best small towns in Ontario for a wee getaway.
A standout Cobourg attraction is its expansive waterfront. The town’s main beach, with its soft sands and shallow waters, is a popular spot for both locals and tourists. During summer, the beach transforms into a hub of activity, with families picnicking, and children building sandcastles, while paddleboarders dot the shorelines. Adjacent to the beach is Victoria Park, a lush expanse that offers shady reprieves and plays host to various festivals and events throughout the year.
The Cobourg Heritage Centre and Victoria Hall, a majestic 19th-century building, provide glimpses into the town’s storied past. These structures offer a glimpse of a bygone era when it was a significant port and a budding resort town, with some of the best places to stay in Cobourg set in historic buildings.
Cobourg’s arts and cultural landscape is as dynamic as its history, and the town boasts galleries, theatres, and venues that host a myriad of events, from music festivals to art exhibitions. The annual Waterfront Festival is a particular highlight, showcasing local artisans and performers.
Huntsville
While vying for the title “the heart of Muskoka” with the equally lovely small towns of Bracebridge and Gravenhurst(yeah, my hometown!), Huntsville is certainly a contender. The most northerly of these three cottage country towns and a two-and-a-half-hour drive from Toronto, Huntsville was founded in the mid-19th century and evidence of its well-preserved heritage can be seen among the many heritage buildings lining its main street.
Huntsville’s cultural scene is equally captivating. The Algonquin Theatre, a central hub for arts and entertainment, showcases a range of performances, from local plays to concerts and film festivals. It’s also home to the must-attend Huntsville Festival of the Arts, a must-stop venue for some of the top performers in Canada.
Be sure to visit some of the town’s art galleries and craft shops, which highlight the talents of local artisans, offering unique pieces inspired by Muskoka’s landscapes. Huntsville’s dining scene is also top-notch, with the town’s many excellent restaurants serving up memorable, often locally sourced dishes.
Huntsville also serves as a great base from which to explore Algonquin Provincial Park, which borders Huntsville to the east. As one of Ontario’s oldest, largest, and best provincial parks, Algonquin is a mosaic of pristine lakes, rugged hills, and dense forests, and boasts a wide range of outdoor adventures. Popular activities here include canoeing and hiking in the summer to snowshoeing and cross-country skiing in the winter. The park’s diverse ecosystem also makes it a hotspot for wildlife viewing, while local outfitters even offer exciting wilderness camping adventures.
To find out more about why we consider Huntsville to be one of the best small towns in Ontario, check out LuxuryHuntsville.com. And for ideas and inspiration regarding great places to stay in Huntsville, check out the following great content:
Enjoy Authentic Muskoka @ The Best Cottage Resorts in Huntsville
Cottage Country Class: The Best Luxury Hotels in Huntsville ON
Bracebridge
Named after a Washington Irving novel, Bracebridge is one of those picture-perfect small towns that seems to have it all. Set overlooking one of the most picturesque waterfalls in Ontario and both branches of the Muskoka River, Bracebridge boasts around 22 falls within its borders, including Wilson’s Falls, High Falls (consisting of five separate falls), and numerous others all within a short drive of the downtown area.
Bracebridge celebrates this unique heritage in many ways. The economic impact of the falls is recorded along the Riverwalk, a scenic trail which offers breathtaking views of Bracebridge Falls from above and below. Culturally, too, the falls continue to be a focal point for visitors. Located at its top is the renovated Bird Mill, home to the Town’s Visitor Centre and restaurants, while nearby the octagonal Woodchester Villa is one of the town’s most important historic landmarks.
Downtown Bracebridge is also fun to explore on foot as the main street rises in tiers of shops, services and restaurants, from the falls, many with vintage architectural facades. Take a little detour and it’s like stepping back in time as you wander amongst stately turn-of-the-century homes and churches.
It’s worth visiting after nightfall, too, as the town’s clock, bell tower, courthouse and “silver bridge” are outlined in unique, colourful lighting. Those with a hankering for culture will want to check out the town’s many art galleries and theatres. And perhaps best of all, Bracebridge has been the summer home of Father Christmas since Santa’s Village opened here in 1955.
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Bryan Dearsley is a luxury lifestyle and travel writer. He’s also a Co-Founder of Riley and LuxuryOntario and is proud to call Muskoka, Ontario, “home.”
