These Towns In Ontario Have The Best Main Streets

As Canada’s most populated province (nearly 50 percent of the nation’s 39 million residents live here), it’s hardly surprising that Ontario should also be home to some of this northern country’s most interesting small towns. The very best of these communities are not only blessed with picture-perfect main streets packed with historical attractions and quaint boutique businesses, but they’re also great destinations for a fun day trip or weekend getaway.

From the well-known tourist hub of Niagara-on-the-Lake all the way north along the vast Niagara Escarpment to beautiful Collingwood on Georgian Bay, these seven towns in Ontario have the best main streets and are just waiting to be explored.

Niagara-on-the-Lake

The best-known of the small towns included in this list, Niagara-on-the-Lake owes its popularity not just to its proximity to Canada’s most visited tourist attraction, Niagara Falls, but also to its charming main street. Founded in 1781, downtown “NOTL,” as it’s known to locals, is widely considered one of the prettiest in Canada, especially around Queen Street, the main drag. Lined with many extremely well-preserved 19th-century buildings, it's also where you’ll find the town’s top attractions. These include the Shaw Festival Theatre, which opened in 1973 and is still staging world-class performances and plays, and the iconic Prince of Wales Hotel, a historic landmark that has been welcoming guests since 1864 (it also serves up one of the best afternoon teas in the province).

Niagara-on-the-Lake has also played a major role in Canadian history, particularly during the War of 1812, when it was the site of several key battles between British and American forces. Today, Fort George National Historic Site on the shores of Lake Ontario is a fascinating relic from this tumultuous period and can be reached from downtown NOTL via a pleasant 20-minute stroll along Queen Street. Be sure to plan a meal at one of the many great restaurants along Queen Street, too. In addition to great food, eateries like the excellent Cannery Restaurant at Pillar and Post Inn proudly serve local wines from Niagara-on-the-Lake’s best wineries. Immensely walkable, Queen Street is also home to a variety of boutique shops, galleries, and restaurants, making it a wonderful destination for some souvenir hunting, too.

Collingwood

Founded in 1858 at the northernmost tip of the Niagara Escarpment, some 140 miles from Niagara Falls, the lovely small town of Collingwood is Ontario’s best “all-season” getaway destination. Located on the southern shores of Georgian Bay, the town’s main street, Hurontario Street, is a lovely place for a wander. Stretching from the picturesque Collingwood Harbour, once a bustling shipbuilding port, a mile or so to the grand old Victorian-era homes in the southern part of town, this bustling thoroughfare is lined with well-preserved 19th-century architecture, including the picture-worthy Federal Building and several historic churches.

Numerous shops, galleries, and restaurants also line Hurontario Street, many of them housed in carefully restored heritage buildings. If you’re planning an overnight stay, consider the 1890s Dorchester Hotel, now fully refurbished and located right on Hurontario. Visiting in winter? Collingwood is just a few miles away from Blue Mountain Resort, one of Ontario’s premier skiing and outdoor recreation destinations.

Stratford

Head due west from Toronto, and after an hour or so, you’ll wind up in lovely Stratford. Established in 1832, this postcard-perfect town is named after Stratford-upon-Avon in England and shares a connection with “the Bard”: William Shakespeare. While the pretty town in the UK is famous as the birthplace of the great English playwright, Ontario’s namesake is better known as the hometown of the world-renowned Stratford Festival. The town’s main street, Ontario Street, is a charming blend of historic architecture and modern amenities with plenty of shops, cafés, and restaurants to explore, many of them housed in beautifully restored Victorian-era buildings.

Main street must-visits include the Avon Theatre, constructed in 1900 and one of the festival’s main venues, and the Shakespearean Gardens, a lovely green space adjacent to the river. The festival itself has been around since 1953 and lures countless theatergoers to the town’s bustling main street.

Goderich

Founded on the shore of Lake Huron in 1827, Goderich’s picturesque main street is a great place to visit for a day trip or weekend getaway from Toronto (it’s also just a 90-minute drive north of the Canada - US border). “The Square,” as the town’s main street is known, is a unique octagonal layout that sets it apart from other Ontario towns. This unique and picturesque townscape is surrounded by historic buildings, most notably the Huron County Courthouse and the Goderich Gaol, both of which date back to the 19th century.

Goderich is so pleasant a place to visit that you won’t be surprised to learn that it was dubbed the “Prettiest Town in Canada” by none other than the late Queen Elizabeth II during a visit in 1959. The town was also a key port on Lake Huron, particularly during the late 19th century when it served as a hub for the salt mining industry. Today, Goderich’s main street is a focal point of events, including the annual Celtic Roots Festival, which is a celebration of the town’s Scottish heritage.

Picton

The pretty town of Picton is located in Prince Edward County, a unique geographic region set on an island on Lake Ontario that’s roughly mid-way between Toronto and the Canadian capital city of Ottawa. Picton Main Street is very much the heart of the tourist action here and is a delightful stretch that reflects the area’s rich agricultural heritage. Key attractions include the Regent Theatre, a historic cinema that dates back to 1922, and the unique Crystal Palace, an exhibition hall that hosts various community events that was built in 1887.

From Main Street, it’s only a short stroll to Picton Harbour, an excellent spot to watch the world go by, or hop aboard a charter boat for some fishing or a trip to the remarkable Sandbanks Provincial Park, the world's biggest baymouth barrier dune. Picton Main Street is also a great place to sample some Prince Edward County (PEC for short) wines, with popular restaurants like Bocado and Vic Social serving up some of the best.

Huntsville

Huntsville is located in the heart of Ontario’s Muskoka region, an area of outstanding natural beauty that’s known as the province’s “Cottage Country.” Huntsville Main Street is certainly pretty, especially where it crosses the Muskoka River. The top attraction along Main Street is the Algonquin Theatre, home to the popular Huntsville Festival of the Arts (HFA), a year-long smorgasbord of world-class music, art, and entertainment that’s been running since the 1990s.

There’s easy access to the Muskoka River and the town’s waterfront park area from Main Street, too. Town Dock Park is where you’ll want to pick up a canoe or pedal boat rental to explore the navigable river, while River Mill Park offers seating, docking, and a public performance space. Although not quite downtown, the Lions Lookout is just a short drive away and offers superb views over the town and Fairy Lake, with especially pretty views during the fall as the trees change color. Finally, Huntsville’s proximity to Algonquin Provincial Park is another big plus.

Perth

Perth makes for an excellent day trip from the larger cities of Kingston and Ottawa. Established in 1816 and only an hour’s drive from the nation’s capital, the town’s main street, Gore Street, is a picturesque thoroughfare that reflects Perth’s rich history. Top attractions located along Gore Street include the Perth Museum, which is housed in the historic Matheson House dating from 1840 and is full of fascinating local history, and Stewart Park, a delightful green space that’s perfect for a picnic.

A great time to visit Perth’s downtown area is during the Stewart Park Festival. Held every July, this popular event draws the crowds to the main street area for a celebration of music with plenty of fun activities for people of all ages, including beer and food vendors and even (plastic) duck races. A fun fact that’s often overlooked is that Perth’s history is closely linked to the military settlements established in the area following the War of 1812, with the town playing an important role in the early settlement of Eastern Ontario, with its main street a focal point of community life for over two centuries.

The Final Word

Ontario's small town main streets are the perfect way to get to know more about Canada’s most populated province. Brimming with history, culture, and no end of natural beauty, these still bustling thoroughfares today not only serve as commercial hubs but also as popular tourist attractions boasting plenty of fun things to do. From Huntsville’s connection to Algonquin Park to Stratford’s world-renowned Shakespearian festival, these delightful towns in Ontario, Canada, have the best main streets.