The shopping district of the town Niagara-on-the-Lake, Ontario, Canada. Editorial credit: Dennis MacDonald / Shutterstock.com

11 Of The Most Captivating Small Towns In Ontario

Skirting the shores of four Great Lakes, blessed by the grandeur and unique ecosystems of the Niagara Escarpment (a UNESCO Biosphere Reserve), and energized by some of the most populous regions in all of Canada, Ontario is a captivating place. And while there is value to be gleaned from the big-city economic engines, the true soul of the "Heartland Province" comes from its waterfront, forested, and rural towns. There are a lot of contenders to consider, but having been born and raised in Ontario, these are 11 picks that I find most captivating.

Tobermory

Port with boats in Tobermory in Scotland
Port with boats in Tobermory in Scotland. Image credit Lasse Johansson via Shutterstock.

Teetering at the tip of the Bruce (aka Saugeen) Peninsula, the harbor town of Tobermory is full of surprises. For starters, it is home to two incomparable national parks. Bruce Peninsula National Park enshrines the exquisite Georgian Bay shoreline, with its limestone cliffs, resilient cedars, and turquoise waters, while Fathom Five National Marine Park (i.e. the first of its kind in Canada) encompasses 19 islands and the 20+ shipwrecks in between. These mixed-medium playgrounds open up a deluge of hikes, boat tours, and diving opportunities. But Tobermory has a laid-back social side to it as well. As with any great summer lake town, fish n' chips and ice cream are always on special, and a solid coffee and pub culture has emerged to make those inclement days extra cozy.

Little Current

Golden hour at Little Current, Manitoulin Island, Canada
Golden hour at Little Current, Manitoulin Island, Canada

Speaking of Georgian Bay, this arm of Lake Huron (which is so big it's often called the "Sixth Great Lake") is home to the Manitoulin Island. On this, the world's largest freshwater island, there are many tiny towns worth checking out, but the most engaging is that of Little Current. Flanked by the Little Current Swing Bridge, which connects to Northern Ontario, the smaller islands of the archipelago, and the docked boats of all sorts, Little Current has a grounded, yet transient vibe to it. Whether they arrived by land or water, seasonal visitors come and go along the aptly-named Water Street, with its adorable array of small businesses - each cladded in a different color siding. Another gathering point is the Manitoulin Brewery, not just for its craft beer, but for the outdoor bar, picnic tables, and food trucks.

Cochrane

Cochrane as seen across Lake Commando
Cochrane as seen across Lake Commando, By P199 - Own work, CC BY-SA 3.0, Wikimedia Commons

Many of Ontario's captivating towns rely on summer tourism, but the most northerly entry on this list leans enthusiastically into winter. Cochrane's standout attraction is its Polar Bear Habitat - the only non-profit facility in the world dedicated to the care of the largest living ursines. Located about 250 kilometers south of polar bears' natural boundary, Cochrane does a commendable job of mimicking an authentic environment - one that allows the public to safely observe these apex predators of the Arctic. Taking full advantage of its boreal backdrop, the Cochrane region also boasts 650 kilometers of groomed snowmobile trails (regarded as the best in the province), and a Snowmobile Museum to boot. With all that said, Cochrane does have a summery side to it. Fair-weather visitors should make for Commando Lake, where they can relax on the park beach, launch a standup paddleboard, and catch the weekly concert series, Live at the Lakeside.

Collingwood

Tourists and visitors in the Blue Mountain Village in Collingwood, Ontario, Canada.
Tourists and visitors in the Blue Mountain Village in Collingwood, Ontario, Canada. Editorial credit: Lester Balajadia / Shutterstock.com

Situated on the southern shore of Georgian Bay, Collinwood is happy to oblige both summer and winter visitors. As a kid, I used to frequent Blue Mountain Ski Resort - one of the best downhill skiing destinations in Ontario. Granted, the centralized province is far from any serious mountain ranges, but Blue Mountain still steps up to the task. Its 365 skiable acres are covered by 7 chairlifts and 42 runs (30 of which are lit for night skiing). Once the snow melts, mountain bikers can swarm the slew of cross-country and downhill mountain biking trails throughout Blue Mountain. Or, for a more serene outdoor experience, South Bay Fields Lavender Farm (located just two minutes south of town) is in full bloom and open to the public just for the month of July. And in that tantalizingly short (but all the more beautiful for it) fall season, it's time to enjoy the blanket of colors atop the famed Niagara Escarpment.

Creemore

Street view in Creemore, Ontario
Street view in Creemore, Ontario, By P199 - Own work, CC BY-SA 3.0, Wikimedia Commons

On the way up to Collingwood, check out the adorable escarpment village of Creemore (part of the Clearview Township). With its rusty-brick buildings, and clean, crisp aesthetic, this place has an old fashioned charm to it. But the businesses housed within those timeless facades are also quite engaging. As the name suggests, Creemore Springs Brewery - a craft staple around the Greater Toronto Area - is based here. Pop on by to get it straight from the source. Creemore's coffee culture is also on point. The Bank Cafe exudes a sort of Gilmore Girls vibe, the Flying Squirrel Motorcycle Co. takes up the edgier, biker-based theme (though no less welcoming), and the Creemore Bakery & Cafe specializes in those sweet treats that scream vacation mode. Add in a Saturday farmers market, a robust arts scene, another serene lavender farm, and a couple captivating annual festivals, and it's easy to see how Creemore has earned the slogan: "Little Village, Big Heart."

Stratford

Red brick city hall with a clock tower in the scenic historic center in Stratford, Ontario
Red brick city hall with a clock tower in the scenic historic center in Stratford, Ontario. Editorial credit: Brester Irina / Shutterstock.com

Another gem of southwestern Ontario is the delectable Shakespearean enclave of Stratford. Perched on the Avalon River/Lake Victoria and speckled with opulent Victorian structures, downtown Stratford is effortlessly arresting. The annual Stratford Festival (formerly the Stratford Shakespeare Festival) runs from April through October in various venues across town. While many plays are still tailored to the Elizabethans in attendance, contemporary performances have been steadily added since its inception in 1951. On that note, don't forget about the Stratford Summer Music Festival, when orchestral, choir, jazz, classical, and other stylings all converge on the town's remaining indoor and outdoor stages. Another of Stratford's crowd-pleasing traits is its Chocolate Trail. This indulgent, self-guided tour welcomes sweet tooths year-round. All you have to do is purchase your trail voucher and then stroll the enticing downtown street,s deciding which six of the dozens of participating retailers to patronize.

Grand Bend

Street view on cloudy summer day in Grand Bend, Ontario
Street view on cloudy summer day in Grand Bend, Ontario, via Daxus / iStock.com

The "beach town" crown for the Lambton Shores area clearly goes to Grand Bend. This designation is not just in the sense of having a sandy stretch (for there are several Blue Flag awarded beaches on this part of Lake Huron) but also its propensity for ice cream parlors that serve out a little window, bathing suit and board shops, and Mexican/Caribbean-themed patio bars. But don't worry, if your introverted side needs a breather, Grand Bend is adjacent to Pinery Provincial Park - better known simply as "the Pinery." The Pinery has a 10-kilometer beach of its own, but this one has more sand dunes and less beach balls, plus there are hiking trails through the rare Oak Savannah habitat, and paddle boats for rent along the wide, tree-lined Old Ausable Channel.

Dundas

Dundas Street in downtown Napanee with woman walking on sidewalk in distance
Dundas Street in downtown Napanee with woman walking on sidewalk in distance

My undergrad at McMaster University showed me not only unexpected sides of Hamilton (aka "the Hammer"), but also the adjoined community of Dundas. Tucked away in an idyllic glacial valley beneath the Niagara Escarpment, just off the western tip of Lake Ontario, Dundas enjoys a wealth of nature trails and waterfalls. Leading the charge is the 1,200-hectare Dundas Valley Conservation Area, where I, and my cross-country comrades logged many, many miles through the rolling hills and Carolinian forests each weekend. Other satellite havens include the Christie Lake Conservation Area, Tiffany Falls Conservation Area, and the RBG Cootes Paradise Sanctuary. Who would have thought that an area founded on heavy industry could have such bountiful nature! When the day's explorations have concluded, congregating in downtown Dundas, with its boutique shops, cafes, dual breweries, and worldly restaurants, is sure to be equally enjoyable.

Red Rock

Red Rock, Ontario, Canada
Red Rock, Ontario, Canada

The town of Red Rock is set against the backdrop of the eponymous mountains (easily spotted with their robust red rock bands that are attributed to volcanic origin) and the sheltered splendor of Nipigon Bay — a north shore offshoot of Lake Superior. And while this quiet, early 20th century mill town makes for a relaxing, off-the-beaten-path getaway at any time, it takes on a more magnetic quality during the second weekend in August. The annual, volunteer-driven, Live from the Rock Folk Festival brings in thousands of music lovers to watch dozens of top-tier talents do their thing. Be sure to book a room at the historic Red Rock Inn, which, built in 1937 with a Neo-Georgian style, is equal parts Kubrick-creepy and captivating. Before leaving town, I recommend hiking some of the Nipigon River Trail — at least to the first platformed lookout above the expansive bay and sea of evergreens.

Niagara-on-the-Lake

View of Niagara-on-the-Lake
View of Niagara-on-the-Lake. Editorial credit: Kiev.Victor / Shutterstock.com

Over on the southern shore of Lake Ontario, right on the border with Upstate New York, Niagara-on-the-Lake is one of the most cherished destinations in Canada. This early 19th century hamlet sits in the heart of Ontario Wine Country (with 40 wineries in its vicinity) and just 30 minutes north of the magnificent Horseshoe Falls of Niagara Falls. Niagara-on-the-Lake was designated as a National Historic Site of Canada thanks to its plethora of homes, churches, and commercial buildings erected post War of 1812 (specifically, between 1815 and 1859), as well as the satellite military compounds of Fort George and Butler's Barracks. But historical significance aside, NOTL's elegant streets are filled with engaging galleries, theatres, upscale bistros, and nifty boutiques, and on the outskirts of town, the 856-seat Shaw Festival Theatre gladly entertains tourists with the works of not only George Bernard Shaw, but other popular adaptations.

Port Stanley

An aerial view of Port Stanley, Ontario, Canada
An aerial view of Port Stanley, Ontario, Canada

Introducing yet another of the Great Lakes to Ontario tourists is the village of Port Stanley, which resides on the north shore of Lake Erie. With its sandy, Blue Flag designated Long Beach, combined with the fact that Lake Erie is the shallowest, and therefore, warmest of the Great Lakes, Port Stanley is a swimmer's paradise. On the east side of the lengthy, lighthouse-tipped Port Stanley pier and Kettle Creek, the also-aptly-named Little Beach serves as a worthy alternate chill-out spot. Follow the creek further inland to the historic King George VI Lift Bridge (the oldest of its kind in Ontario), which provides access to the popular and jovial marina, and the Port Stanley Terminal Rail (which regularly puts on fun events, such as Murder Mysteries aboard the train). Otherwise, the plentiful outlets for coffee, books, vintage goods, art, and grub are sure to capture one's attention.

Parting Thoughts

Whether you're ready to swim, hike, ski or people-watch on a relaxing patio, these Ontario towns are up to the task. Sure, the coastal and mountain provinces are rich in assets, but Ontario is more than just the economic, political, and residential center of Canada. It offers incredible access to the great outdoors, and a near constant stream of captivating small towns.

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