Ontario is a province filled with charming small towns in between all kinds of landscapes just waiting to be explored. Among our list are ten of the prettiest towns in Ontario offering a unique blend of beauty, history, and attractions. Whether you’re looking for day trips from Ottawa, fun places in Ontario for summer adventures, or a tranquil escape into the countryside, these enchanting destinations are sure to create unforgettable memories.

As a new Permanent Resident in Canada or a new Canadian citizen, you can join Canoo for free and access deals on car rentals that will help you travel to these incredible spots.

Niagara-on-the-Lake

Along the Niagara River and just a short drive from Niagara Falls, Niagara-on-the-Lake is a town known for its charm. With its tree-lined streets, preserved 19th-century buildings, and lush gardens, it’s no wonder this charming town is often called one of the prettiest towns in Ontario. You can spend your days exploring historic sites, such as Fort George and the Laura Secord Homestead. Or try indulging in the wine at the region’s many vineyards. You can also simply stroll along the scenic waterfront enjoying breathtaking views of Lake Ontario.

St. Jacob’s

Tucked away amidst the hills of southwestern Ontario, St. Jacob’s is a charming village famous for its busy farmer’s market, quaint shops, and Mennonite heritage. You can spend hours browsing through the market’s stalls, sampling fresh produce, baked goods, and artisanal crafts. For a taste of rural Ontario life, you can also take a leisurely drive through the countryside, admiring the picturesque farms and sights that surround the town.

Elora

Along the Grand River, Elora is a hidden gem that captivates visitors with limestone architecture, cascading waterfalls, and riverside restaurants. The town’s historic downtown area is a treasure trove of boutiques, art galleries, and cozy cafes. Don’t forget to visit nearby attractions, such as the Elora Gorge Conservation Area for an outdoor adventure. You can hike along trails, paddle down the river in a kayak or canoe, or relax and soak in the natural beauty of this charming town from a restaurant patio.

Photo of buildings in Elora, Ontario on the waterfront. — Credit: Jason Ng

Merrickville

Stretching from Ottawa to Kingston, the Rideau Heritage Route is a picturesque region dotted with charming towns. One of these towns is Merrickville, known for its European-inspired architecture and scenic waterfront. You can spend time browsing antique shops or take a boat ride along the Rideau Canal. For history buffs, the Blockhouse Museum offers fascinating insights into the region’s military past, while outdoor enthusiasts can enjoy hiking, cycling, and birdwatching in nearby conservation areas.

Goderich

Situated along the shores of Lake Huron, Goderich is a picturesque town with stunning beaches running beside Victorian-era architecture. Explore the heritage buildings that house charming shops and restaurants throughout downtown neighbourhoods. The town’s boardwalk also offers breathtaking views of the lake and surrounding countryside. Nearby spots, like the Huron Historic Gaol and Point Farms Provincial Park, provide opportunities for history and nature lovers alike.

Bala

In Muskoka, you’ll find Bala. This small lakeside town is a natural beauty and outdoor recreation opportunities that is not talked about enough. You can wander through the town’s shops and cafes, relax on the shores of Lake Muskoka to try some fishing and boating. In the winter months, the nearby slopes of Mount Morrisey offer excellent skiing and snowboarding opportunities, making Bala a year-round destination for outdoor enthusiasts. Don’t forget to check out if there is any live music at the Kee to Bala – its stage has seen many famous Canadian musicians perform!

Tobermory

At the northern tip of the Bruce Peninsula, Tobermory is a picturesque waterfront town surrounded by rugged cliffs and turquoise waters that you can’t find anywhere else in Ontario. Visit the town’s historic lighthouse or go on outdoor adventures by hiking, kayaking, and scuba diving. Boat tours to Flowerpot Island will bring you to ancient caves, towering cliffs, and unique rock formations. But you can also visit the Bruce Peninsula National Park (for free with Canoo) to immerse yourself in the region’s natural beauty.

Person standing at Tobermory cliffs - one of the prettiest towns in Ontario. — Credit: Warren

Gananoque

As the Gateway to the Thousand Islands, Gananoque is a charming waterfront town surrounded by deep waters, lush forests, and so many islands. Boat tours of the Thousand Islands provide opportunities to explore hidden coves, historic lighthouses, and stunning natural landscapes while learning all about the bootlegging pirates that used the islands as hiding spots during the early 20th century! You can also visit the Thousand Islands Playhouse and the Arthur Child Heritage Museum for insights into the region’s long history and culture.

Collingwood

Along the shores of Georgian Bay, the Collingwood area is truly a special spot. Spend your days hiking, mountain biking, or skiing through the region’s mountains. You can also explore charming towns, like Thornbury, with its small shops, fresh bakeries, and fun cideries. In the summer months, the region’s beaches provide opportunities for swimming and kayaking. Meanwhile in the winter, the slopes of Blue Mountain have world-class skiing and snowboarding. If you follow up this day on the slopes with a beavertail, you’ll feel a little extra Canadian.

Stratford

Known for its annual Shakespeare Festival, Stratford is a charming town brimming with cultural attractions and historic architecture. You can spend your days exploring the historic downtown where beautiful heritage buildings house charming shops and galleries. After a nice dinner, you can follow up that perfect date night with a show at the Festival Theatre! It’s the ultimate romantic getaway out of the city and into the countryside.

Whether you’re seeking outdoor adventure, cultural experiences, or simply a peaceful retreat, these enchanting destinations provide the perfect backdrop for unforgettable memories and lasting experiences. So pack your bags, hit the road, and embark on a journey through the prettiest towns in Ontario.

If you’re interested in planning a road trip to see the prettiest towns in Quebec, click here to see Canoo’s full list!