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Ontario offers more than just the bustling cityscapes of Toronto. Its vast borders are filled with tons of small towns and quaint communities that make up much of its population outside of the major metro areas.

From popular yearly festivals to historic quarters and pristine urban greenspaces, we'd like to explore some of the best of what these cozy destinations have to offer. Embark on a trip with us to these highly recommended downtown areas in the province you can visit today, many of which are within driving distance of the Greater Toronto Area.

Niagara-on-the-Lake

The town of Niagara-on-the-Lake makes for a great place to stop if you happen to be heading down to the º£½ÇÉçÇø-famous Niagara Falls. Whether you want to stop somewhere good to eat or simply want to check out its picturesque streets and waterfront area, it is a must-visit for tourists.

The town’s walkable layout makes it easy to explore on foot, with shaded sidewalks leading to landmarks like the Prince of Wales Hotel and the Niagara Apothecary, a restored 1869 pharmacy-turned-museum. Seasonal floral displays and urban park spaces, including Simcoe Park, add to the downtown core's beauty.

Dining in Niagara-on-the-Lake ranges from casual eateries to high-end restaurants, many of which feature local produce and wines from nearby vineyards in the renowned Niagara wine region. If this interests you, be sure to pay a visit to popular spots like Jackson-Triggs Niagara Estate or the Peller Estates Winery And Restaurant.

The town’s close proximity to Niagara Falls and the Niagara Parkway cycling route adds another layer of appeal for visitors seeking to see the area up close.

Bobcaygeon

Bobcaygeon, made famous by the popular The Tragically Hip song of the same name, has a pleasant downtown in the heart of the Kawarthas that sits between Sturgeon and Pigeon Lakes. Its healthy selection of waterfront patios, restaurants, and hotels make it a top-tier vacation spot just a couple hours north of Toronto, while historic buildings like Bigley Shoes and Clothing, a regional landmark since 1911, anchor the shopping scene alongside several other locally owned boutiques.

The Bobcaygeon Swing Bridge, which opens for boat traffic along the Trent-Severn Waterway, is another central feature and a favorite viewing spot during the boating season in the warmer months. Moreover, Lock 32, the first lock built on the waterway, sits at the heart of downtown and offers you a picturesque green space and a place to watch boats pass through. Various waterfront trails also make it easy to explore the surrounding lakes on bike or foot.

Dining options range from lakeside patios to cafes and upscale dining establishments, many within walking distance of the docks. Eateries like Grâz, The Royal Moose Grill & Waterfront Patio, and Wheatsheaf Café are all highly recommended and are located just steps from the Bobcaygeon River.

Must-visit events like the Bobcaygeon Craft Beer & Food Festival and the annual Fall Fair bring added energy to the town, while public docks and ample parking make downtown easily accessible for both boaters and drivers, leading to this small town being a top destination to visit in Ontario all year long.

Stratford

Stratford’s downtown is known for its dedication to performing arts, along with other draws like locally-run events and tons of greenspaces to have some fun outdoors.

Market Square, directly behind City Hall, serves as the main community hub, regularly hosting farmers' markets, craft fairs, and other seasonal events throughout the year. Speaking of, the Stratford Festival, running from spring to fall, anchors the town’s art scene, with the Avon Theatre located directly downtown hosting a range of productions. Furthermore, the Stratford Garlic Festival and Summer Music Festival add yet more community activities to partake in.

Moreover, The Stratford Perth Museum, a short walk from downtown, offers rotating exhibits on local history and culture dating back to the town's founding and beyond.

Natural features like the Avon River are easily accessible, where you can explore on water via canoe or kayak or walk the riverside trails lined with woodlands. For something to do in town, the Arthur Meighen Gardens is a wonderful greenspace to go for an easy stroll among themed gardens and lily ponds.

Picton

Picton’s downtown centers around notable landmarks like the historic Regent Theatre, operating since 1922. Just a few steps away, the Picton Armoury serves as another local arts hub, hosting markets, exhibits, and community events as well.

Food and drink are also key draws in this Prince Edward County community, with craft breweries, farm-to-table restaurants using locally sourced ingredients, and cafes filling the downtown blocks. Highly rated joints like Vic Social and The Acoustic Grill make this town well worth a stop for its cuisines alone.

If you're here to try the region's delicious wines, you can follow the Prince Edward County Taste Trail, which connects downtown to nearby wineries, cideries, and cheesemakers. For more local offerings, the Picton Farmers’ Market, held weekly, brings local produce, baked goods, and handmade crafts directly to the town square.

For outdoor activities, Macaulay Heritage Park offers nature trails, gardens, and a historic church-turned-museum just south of downtown. The waterfront at Picton Harbour provides boat access, walking paths, and quiet spots to take in views of the bay.

Perth

Perth’s downtown, centered around Gore Street, blends wonderful historic stone architecture with a highly walkable mix of shops, restaurants, and galleries. Start by learning more about this small southern Ontario town at the Perth Museum. Housed in the Matheson House, built in the 1840s, it gives a detailed look into the town’s early days and is a great example of the old building that can be found here.

Set in a very rural area, Perth’s food scene focuses on highlighting local producers, with options ranging from craft breweries to bakeries and even some fine dining. The Perth Cheese Shop and Code’s Mill Market are popular stops for regional goods.

The town's smaller size also makes walking simple, and events like the Perth Garlic Festival and Stewart Park Festival are big draws for those who want to celebrate Perth's community spirit while exploring on foot.

In the heart of town is Stewart Park, situated on an island in the middle of the Tay River. Here, a web of walking trails, picnic spots, and even a performance stage that comes alive during summer festivals are there to greet you. Numerous bridges connect the island to the rest of Perth, making it easy to get to from multiple areas downtown.

Cobourg

Cobourg’s downtown stretches along King Street, where many of its most popular amenities and landmarks can be found. One notable destination is the Victoria Hall, a 19th-century civic building where concerts, art shows, and community events. Within the same building, the Art Gallery of Northumberland is another main artistic attraction that with various exhibits on rotation throughout the year.

A short walk from downtown leads to Cobourg Beach and Victoria Park, where boardwalks, viewpoints over Lake Ontario, and waterfront trails create an idyllic natural extension of the town center. Annual events like the Sandcastle Festival and the Cobourg Waterfront Festival provide more fun options for the whole family. The Cobourg Marina also makes for a nice spot to park/launch your boat on the lake if you're looking to spend some time on the water this summer.

Elora

Elora’s downtown is compact but packed with lots to see and do, all set against the backdrop of its 19th-century limestone buildings. Mill Street is one of the main attractions, leading directly to the Elora Mill Hotel & Spa, a restored 1832 mill perched above the Grand River.

The Elora Gorge is the area’s biggest natural attraction, with trails, lookouts, and tubing routes running through its limestone cliffs. Access points to the gorge are within walking distance of downtown, making it easy to combine shopping and dining with outdoor activities.

Art plays a central role in the town’s identity too, with galleries like the Elora Centre for the Arts and numerous local studios scattered around downtown.

For a tasty refreshment while visiting, locales like the Elora Brewing Company and Elora Distilling Company are great spots to hang out, while places like The Friendly Society, a cozy cafe, and The Cellar Pub And Grill, a riverfront pub, offering meals through the day.

Port Perry

Port Perry is renowned for its heritage brick buildings, community events, and proximity to Lake Scugog. Among the best ways to experience the natural beauty of the area is to pay a visit to Palmer Park, a gorgeous urban green space along the lake's extensive shoreline where you will also find the Port Perry Marina, making it a key spot to launch your boat.

Another recommended stop is the Scugog Shores Museum Village, which highlights the region’s storied history dating back to the 1800s, and the Town Hall Theatre, a small yet ornate venue that hosts plays and live music. The adjacent Queen Street is also lined with an array of restaurants, pubs, and coffee shops, many offering lake views from patios or upper floors. A short walk around the corner will land you at Old Flame Brewing Co. Located in a restored historic building, this quickly growing brewery offers craft beer tastings in its large taproom right in the heart of downtown.

Seasonal events like the Port Perry Waterfront Ribfest, a delicious celebration with a huge selection of local food vendors, and the Scugog Arts Studio Tour, an excellent way to see local artists, bring added crowds in the spring and summer months.

Huntsville

Huntsville sits in the Muskoka region, the heart of Ontario's cottage country, and is well-known as the main gateway to nearby Algonquin Provincial Park, one the largest and most visited parks in the province. Aside from its proximity to numerous natural landmarks and vast wildlands for outdoor adventure, the downtown core of Huntsville is very much worth exploring too.

A walk around town will take you by several murals depicting scenes from figures like Tom Thomson and the Group of Seven, a group of artists whose legacy of painting natural scenes of the region keeps them relevant decades after they departed. See some of this pristine nature for yourself at River Mill Park. Located near the town docks, this city park serves as a gathering spot with walking trails, picnic areas, and a playground. The park is the location of popular local events too, like the Huntsville Art Crawl and numerous summertime concerts. From here, you also can access the Muskoka River by kayak or boat.

Downtown Huntsville is home to a number of useful amenities as well, with a great selection of outdoor outfitters you can visit before your adventure, restaurants, hotels, and other kinds of shops available.

Just beyond downtown, the Lions Lookout Trail provides panoramic views of the town and surrounding lakes, while nearby Arrowhead Provincial Park offers an alternative to Algonquin for hiking, canoeing, and winter cross-country skiing trails.

Experience Smalltown Ontario Today

Get outside of Toronto, Ottawa, or any of the other big metro areas of Canada's most populous province. From riverside parks and waterfront trails to local markets and seasonal festivals, these amazing destinations in Ontario will give you authentic ways to connect with each town’s character. Whether it’s walking heritage streets in Perth, exploring the wonders of the Elora, or enjoying lakeside views in Bobcaygeon, each spot mentioned above is definitely worth a visit this year.