7 Of The Quirkiest Towns In Ontario
As Canada's most populous province (nearly 40 percent of the country lives here), Ontario boasts no end of quirky towns worth visiting, each with its unique charm. Along with their distinctive experiences and fascinating histories, these towns also reflect Ontario’s rich cultural and geographical diversity, with everything from picturesque waterfronts to exciting art scenes to explore.
From the renowned Shakespearean theater festival in lovely Stratford to the historic cottage country destination that is Gravenhurst in Muskoka, these seven quirky towns in Ontario continue to attract visitors from the United States and beyond, all of them looking for an authentic Canadian travel experience.
Niagara-on-the-Lake
One of the most popular tourist destinations in Canada, Niagara-on-the-Lake isn’t without its quirky side. Located at the mouth of the Niagara River, where it meets Lake Ontario, and just a few miles away from both the Canadian and American sides of Niagara Falls, NOTL, as it’s affectionately known, is renowned for its historical significance and its exciting cultural scene. Established in 1792, it was the first capital of Upper Canada, and its historical importance is evident in its well-preserved 19th-century architecture and landmarks, most notably Fort George, a key location in the War of 1812 that today offers guided tours and reenactments.
The annual Shaw Festival, named after playwright George Bernard Shaw, is another major draw and offers a rich program of theatrical performances. NOTL is also famous for its wineries and vineyards. All told there are over 50 to choose from, including celebrity-owned establishments such as Dan Aykroyd’s Diamond Estates and Wayne Gretzky Estates, owned by the Canadian hockey legend.
Gravenhurst
Gravenhurst is located in the Muskoka region of Ontario and first made a name for itself when the region got on the radar of wealthy American industrialists from places like New York and Pennsylvania looking for a summer escape. Arriving by train from Toronto, it was in Gravenhurst they’d board the steamships that would ferry them and their belongings around Lake Muskoka to their summer cottages and compounds. Fast forward to today and this “Cottage Country” legacy lives on, but now it’s Hollywood elites like Tom Cruise and Brad Pitt who fly in each summer. And Gravenhurst’s steamship legacy lives on thanks to the RMS Segwun, Canada's oldest still-operating steamship and the sole survivor of the original Muskoka steamship fleet, still going strong after 137 years, offering visitors fun scenic cruises.
The town itself is very walkable, with many of the older homes and businesses built at the end of the 19th century still intact. One of the most notable is Bethune House, home to the legendary Doctor Norman Bethune, who died in China while helping care for wounded soldiers in 1939. The pretty Gravenhurst Opera House, built in 1891 along with the town’s Carnegie Library, is also worth checking out and has hosted numerous big stage names such as the late Donald Sutherland, who cut his teeth here in the early days of his career. Just a few steps away is Sawdust City Brewery, named after Gravenhurst’s quirky logging-era nickname.
Stratford
Located in southwestern Ontario and just 90 90-minute drive from the border with Michigan, Stratford was founded in 1859 and is named after Stratford-upon-Avon in England, the birthplace of William Shakespeare. This connection with England’s Shakespearean heritage was cemented in 1953 with the inaugural Stratford Festival, which today attracts theatergoers from around the world with its diverse array of performances, including Shakespearean plays and contemporary works staged in several theaters around town.
In addition to its sometimes quirky artistic endeavors, Stratford is also noted for its well-preserved historical architecture and charming streetscapes, especially in its picturesque downtown area with its many Victorian-era buildings. Like the town’s namesake in the UK, Stratford, ON, even has its own Avon River, providing opportunities for leisurely walks along its banks, canoe and kayak adventures, and some swan-spotting along the way.
Collingwood
Situated on the southern shore of Georgian Bay, a vast bay off Lake Huron that’s almost as large as Lake Ontario sits the delightful town of Collingwood. Established in 1858 and named after a small town in England, Collingwood started off as an important grain port and shipbuilding yard and has since evolved into a popular destination for tourists and day-trippers. In addition to its endless boating opportunities (it’s, in fact, possible to sail from here all the way to Florida!), outdoor enthusiasts are drawn to its proximity to Blue Mountain Resort, one of Ontario's best ski and mountain biking areas.
You can learn more about the town’s quirky past at the Collingwood Museum, set in the town’s original old railway station and containing many fascinating exhibits relating to its maritime and local history. Speaking of railways, from here, you can actually hike or bike the Georgian Trail along the lakeshore for 21 miles to Meaford. The town also offers walking trails and parks, including the scenic Harbourview and Sunset parks
Port Hope
Port Hope’s location on the northern shore of Lake Ontario between Toronto and Kingston makes it an ideal day trip destination. Established in 1789 and quirkily named after the biblical “port of hope,” the town is notable for conservation efforts that have helped preserve its early 19th-century character. The town’s historic downtown area is home to numerous well-preserved buildings, including the Capitol Theatre, one of the country’s last surviving “atmospheric” venues built in 1930, complete with a medieval courtyard that still hosts regular performances.
The Ganaraska River offers a scenic backdrop for recreational activities such as fishing and hiking and serves as a backdrop for a variety of events and festivals celebrating local culture and history, including the Port Hope Fall Fair. The town was also the home of iconic Canadian author Farley Mowat, a fact that’s honored at a park named after the legend.
Elora
Elora’s location along the Grand River is definitely one of the prettiest in southwestern Ontario. Founded in 1832, Elora soon became an important mill town, and the original mill from this period (it was built the same year) is still standing. Now operating as the Elora Mill Hotel & Spa, this cool, quirky boutique hotel overlooks the beautiful Elora Gorge with its dramatic limestone cliffs and rushing waters and offers some of the best views of this much-photographed and extremely idyllic scene.
In addition to hiking, tubing, and sightseeing, the town’s picturesque setting along the gorge provides a striking contrast to its quaint and historic downtown area. A great time to visit is during the Elora Festival, held each July since 1980, with many musical and artistic performances.
Fergus
Located just a short drive from the “Royal City” of Guelph, Fergus is rightfully proud of its rich Scottish heritage. Founded in 1833 by Scottish immigrants and named after one of the founders, Adam Ferguson, the town’s Scots roots are celebrated at the quirky Fergus Scottish Festival & Highland Games, one of Canada’s largest events connected to Scotland. Highlights of this 70-year old three- day event include traditional events such as caber tossing, Highland dancing, and pipe and drum performances.
Fergus also features historical attractions such as the Wellington County Museum and Archives, a former poor house and farm built in the 1870s that now preserves important aspects of the town’s heritage.
The Final Word
Dotted across Canada’s largest province population-wise, these seven quirky towns stand out not just for their quaintness but also for their intriguing backstories. From the theatrical hotbed that is Stratford to the steamship-era town of Gravenhurst up in Cottage Country, these towns offer a glimpse into Ontario's history, its culture, as well as its natural beauty. Whether you’re seeking artistic inspiration, outdoor recreation, or a little historical exploration, these seven of the quirkiest towns in Ontario are worthwhile stops on any Canada travel itinerary.
