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 played a significant role in Canadian history, especially during the War of 1812 when it was the site of key battles between British and American forces. Today, Fort George National Historic Site on Lake Ontario's shore offers a fascinating glimpse into this turbulent era. It can be reached from downtown NOTL in a pleasant 20-minute walk along Queen Street. Be sure to enjoy a meal at one of the many excellent restaurants along Queen. Besides delicious food, establishments like the Cannery Restaurant at Pillar and Post Inn proudly offer local wines from Niagara-on-the-Lake’s top wineries. Queen Street is very walkable and features a variety of boutique shops, galleries, and eateries, making it an ideal spot for souvenir shopping and exploring.

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, built in 1900 and one of the festival’s main venues, and the Shakespearean Gardens, a lovely green space along the river. The festival itself has been held since 1953 and draws countless theatergoers to the town’s bustling main street.

Goderich

Founded in 1827 on the shores of Lake Huron, Goderich’s charming main street is an ideal destination for a day trip or weekend escape from Toronto, just a 90-minute drive north of the Canada-U.S. border. Known locally as "The Square," the town’s distinctive octagonal layout makes it stand out among Ontario towns. This scenic town is bordered by historic buildings, including the 19th-century Huron County Courthouse and the Goderich Gaol, both prominent landmarks.

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 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 of 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 is an ideal day trip destination from Kingston and Ottawa. Founded in 1816 and just an hour’s drive from the capital, the town’s main street, Gore Street, showcases Perth’s rich history through its charming streetscape. Notable attractions along Gore Street include the Perth Museum in the historic Matheson House from 1840, which offers captivating local history exhibits, and Stewart Park, a lovely green space perfect for picnics.

A great time to visit Perth’s downtown area is during the Stewart Park Festival. Held every July, this popular event draws crowds to the main street for a celebration of music and 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. The town played an important role in the early settlement of Eastern Ontario, and its main street has been 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 Canada’s most populous province. Brimming with history, culture, and endless natural beauty, these still-bustling thoroughfares today not only serve as commercial hubs but also as popular tourist attractions with plenty of fun things to do. From Huntsville’s connection to Algonquin Park to Stratford’s world-renowned Shakespearean festival, these delightful towns in Ontario, Canada, have the best main streets.