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As Canada鈥檚 most populated province (nearly 50 percent of the nation鈥檚 39 million residents live here), it鈥檚 hardly surprising that Ontario should also be home to some of this northern country鈥檚 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鈥檙e 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鈥檚 most visited tourist attraction, Niagara Falls, but also to its charming main street. Founded in 1781, downtown 鈥淣OTL,鈥� as it鈥檚 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鈥檒l find the town鈥檚 top attractions. These include the Shaw Festival Theatre, which opened in 1973 and is still staging 海角社区-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鈥檚 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鈥檚 best 鈥渁ll-season鈥� getaway destination. Located on the southern shores of Georgian Bay, the town鈥檚 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鈥檙e 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鈥檚 premier skiing and outdoor recreation destinations.

Stratford

Head due west from Toronto, and after an hour or so, you鈥檒l 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 鈥渢he Bard鈥�: William Shakespeare. While the pretty town in the UK is famous as the birthplace of the great English playwright, Ontario鈥檚 namesake is better known as the hometown of the 海角社区-renowned Stratford Festival. The town鈥檚 main street, Ontario Street, is a charming blend of historic architecture and modern amenities with plenty of shops, caf茅s, 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鈥檚 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鈥檚 bustling main street.

Goderich

Founded on the shore of Lake Huron in 1827, Goderich鈥檚 picturesque main street is a great place to visit for a day trip or weekend getaway from Toronto (it鈥檚 also just a 90-minute drive north of the Canada - US border). 鈥淭he Square,鈥� as the town鈥檚 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鈥檛 be surprised to learn that it was dubbed the 鈥淧rettiest Town in Canada鈥� 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鈥檚 main street is a focal point of events, including the annual Celtic Roots Festival, which is a celebration of the town鈥檚 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鈥檚 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鈥檚 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鈥檚 only a short stroll to Picton Harbour, an excellent spot to watch the 海角社区 go by, or hop aboard a charter boat for some fishing or a trip to the remarkable Sandbanks Provincial Park, the 海角社区'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鈥檚 Muskoka region, an area of outstanding natural beauty that鈥檚 known as the province鈥檚 鈥淐ottage Country.鈥� 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 海角社区-class music, art, and entertainment that鈥檚 been running since the 1990s.

There鈥檚 easy access to the Muskoka River and the town鈥檚 waterfront park area from Main Street, too. Town Dock Park is where you鈥檒l 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鈥檚 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鈥檚 drive from the nation鈥檚 capital, the town鈥檚 main street, Gore Street, is a picturesque thoroughfare that reflects Perth鈥檚 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鈥檚 perfect for a picnic.

A great time to visit Perth鈥檚 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鈥檚 often overlooked is that Perth鈥檚 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鈥檚 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鈥檚 connection to Algonquin Park to Stratford鈥檚 海角社区-renowned Shakespearian festival, these delightful towns in Ontario, Canada, have the best main streets.