9 Best Small Towns In Ontario For A Weekend Retreat

As spring and summer near, you may find yourself itching for a weekend away–just far enough to be somewhere new, but close enough to not spend your entire weekend traveling. Beyond the borders of Ontario’s famous cities, there is an entire world of small towns whose old-world charm and bewitching natural surroundings will have you wishing you visited sooner. And while cities like Toronto and Niagara are hotspots for good reason, maybe you are looking for something on the quieter side–a peaceful place for a weekend retreat. Whether to fill your days with an outdoor adventure or to savor romantic evenings away from home, depending on what vibe you are after, these small towns have something to entice any traveler’s unique desires. From quaint villages with towering limestone quarries to towns so pretty Hallmark uses their Mainstreet as a film set, here are 9 of the best towns in Ontario for a weekend retreat.

Discover 9 of the most welcoming towns in Ontario.

Niagara-on-the-Lake

Less than 30 minutes from the every-iconic Niagara Falls, you will find the perfect getaway town for a romantic weekend retreat. With a reputation as the “Honeymoon Capital of the World,” you may be wondering how another town could top the romance of the world-famous waterfall–but once you make the detour to Niagara on the Lake, nicknamed “The Prettiest Town in Canada,” the sights speak for themselves.

Although the town’s proximity to the falls is for sure a central perk, Niagara on the Lake is brimming with its own charms, like the British Classical-style buildings, cobblestone streets, and scenic shores of Lake Ontario. Vintage hotels like the Queen’s Landing or Pillar & Post add to the allure of your stay, while more historic accommodations like Oban Inn blend heritage with luxury. Serving the community since 1824, this historic inn prioritizes relaxation, offering a full-service spa and gorgeous garden surroundings. It is also located right in the heart of town near attractions like the Queen Street shopping district and Shaw Festival Theatre.

Adding to the romance, Niagara on the Lake is also famous for its bountiful wineries, and there are several within a 10-minute drive from Oban, like Two Sisters Vineyards and the Peller Estates Winery And Restaurant. For even closer access to this heart of wine country, Riverbend Inn & Vineyard is another gorgeous accommodation option where relaxation thrives. Surrounded by 17 acres of vineyards and intricate gardens, this Georgian mansion-turned-inn is right on Niagara River, meaning the views from any room are stunning. All in all, no matter where you stay in this pretty Ontario town, the ambiance will not disappoint.

Almonte

If waterside views and Hallmark downtowns pique your interest, then Almonte is the perfect choice for a weekend escape–especially for those living closer to eastern Ontario. But with a town this darling, you may even be willing to pack up the car for a road trip. Just 40 minutes from Ottawa’s buzzing downtown, city folk flock to Almonte for its slower pace and ideal small-town feel. Once a mill community, the Mississippi River is an anchoring feature of Almonte, best explored via the Almonte Riverwalk beginning by the town hall. Yet, the river is just a fraction of Almonte’s beauty since the town’s picturesque 19th-century look is why it has been the setting for a ton of holiday films and why the New York Times dubbed it “Mini Hollywood North.

Make your way to downtown Mill Street to see why this Ontario town can pass for Vermont or Milwaukee in these cozy holiday flicks. The main stretch is lined with historic structures like the Victoria Woollen Mill and Old Amonte Post Office, along with adorable shops and restaurants like Almonte Antiques & Collectibles and the Mill Street Crepe Company. Just a minute’s drive from downtown, riverside accommodations like The Monte or historic Menzies House Bed and Breakfast (built-in 1850) are the perfect way to live out your Hallmark fantasy for a few days. Bear in mind Almonte may be especially charming during the wintertime when snow is fresh and holiday festivities are at their peak, but this Ontario town is a perfect weekend retreat year-round.

Perth

Around 40 minutes south of Almonte, Perth is another picturesque Ontario town known for embodying that sleepy and romantic small-town feel. With over 100 designated heritage buildings dotting the town, like Almonte, you will feel transported back in time to the 19th century. The downtown stretch is where you will find many of these Victorian structures, like Code’s Mill, a former mill built back in 1843. A popular wedding venue, the limestone structure is also packed with specialty shops and restaurants like Kelly’s Flowers & Gift Boutique and Fiddleheads Bar & Grill, which has an incredible outdoor patio overlooking Code Park to enjoy dinner with a view.

Speaking of parks–right next door, behind the town hall, Stewart Park is a must-see follow-up. The grounds are enchanted with storybook bridges crossing the Tay River, bright foliage shading the paths with just enough pockets of sunshine to warm you on a picnic or stroll. The Stewart Park Festival is an especially great time to visit, bringing the park to life with live music, vendors, and scrumptious food. In 2024, it is set to take place in July, on the weekend of the 19th to 21st. The Best Western Plus Perth Parkside Inn & Spa is your best accommodation option since it is right next to Code’s Mill and has a ton of neighboring attractions, including parks, the Perth Museum, and Studio Theatre Perth.

Elora

For nature enthusiasts, Elora, “Ontario’s Most Beautiful Village,” is as enchanting as it comes. Straddling the banks of the Grand River on the edge of the Elora Gorge, this town may be tiny, but its landscapes are anything but. The Elora Gorge Conservation Area is the best place to witness the Grand River’s mighty passage through the surrounding 72-ft. cliffs, whether on a riverside trail or with a bird’s-eye view from an overlook. Along with hiking, adventurers can kayak or tube the racing rapids just as soon as the area opens for the season on May 1st, 2024.

Later in the season, (in early June), the Elora Quarry Conservation Area is also set to re-open. The forested 2-acre limestone quarry is a beloved swimming and picnicking spot due to its towering 40-ft. cliffs. Sheltering beachgoers and kayakers from harsh winds, the cliffs are as practical as they are postcard worthy. Other riverside attractions can be found in Elora’s downtown, like Bissell Park, which hosts exciting events throughout the year. Riverfest Elora is one example, which is set to take place August 16th-18th, 2024. The family-friendly music festival is a great time to make Elora your temporary home, and if you plan on enjoying the entire weekend lineup, accommodations like the Elora Mill Hotel & Spa or The Village Inn are both great options. The previous is a more luxurious stay, while the latter is an excellent cost-effective option.

Stratford

If you are looking for another adorable small town with a vibrant festival scene, you may want to plan a trip to Stratford. Named after Stratford-upon-Avon, England, William Shakespeare’s birthplace, the town pays homage to the iconic playwright in many ways, like the Shakespearean Gardens. With more than 60 types of flora–including several featured in Shakespeare’s plays–this charming town feature will begin to take bloom in the upcoming months, so now is the best time to start planning your visit.

The town’s most famous homage though, would be the Stratford Festival, North America’s largest classical repertory theater company. Performances have been held since 1953 across several of the town’s venues, like the historic Avon Theatre. Today, the shows range from the classics (with an emphasis on Shakespeare) to more contemporary musicals and dramas. This year, the festival will span Apr 16th to Oct 27th, 2024, so there is plenty of time to see a show and explore the other parts of this quaint riverside town. Venues like the Tom Patterson Theatre are settled right on the Avon River, making this the perfect way to enjoy a pre-show stroll or stretch your legs afterwards.

A short 2 minute drive (or 8 minute walk) from the Tom Patterson venue will guide you deeper into bustling downtown Stratford, where places like Bentley’s Bar Inn & Restaurant offer classic bar eats and modern suites. Or, if you do not mind a slightly further walk and would prefer a quainter stay, there are also plenty of charming 19th-century bed and breakfasts in the area, like The Old Rectory, The Caversham House, and The Chisholms.

Huntsville

For those looking to spend more time out in nature on their next weekend away, the town of Huntsville is a gateway to some of the best outdoor attractions in the Muskoka region. Around thirty minutes from town, Algonquin Provincial Park welcomes over 800,000 people annually, many staying in Huntsville for quick and easy access. Famous for its towering ridges, 1500 lakes, and rolling maple hills, the beauty of this wilderness haven is as breathtaking as it is vast.

If you would prefer to stay right in town, Huntsville is also home to other natural attractions like the Lions Lookout trailhead overlooking the town, and Limberlost Forest & Wildlife Reserve. The reserve’s 10,000 acres of forest and 20 scenic lakes can be discovered on the 43-mile trail system, whether hiking in the summertime or snowshoeing in the winter. But the town’s crown jewel would have to be Arrowhead Provincial Park, whose 9 miles of attractive trails, three sandy beaches on Arrowhead Lake, and glorious waterfall (found via the Stubb’s Falls Loop) make this one of Ontario’s most sought-after nature destinations. Whether you stay at a lakeside hotel like Deerhurst Resort or opt for a more secluded stay with Jaynes’ Luxury Cottages, nature is truly all around you in this pleasant Ontario town.

Picton

If you are after a more lowkey weekend of Main Street strolls with a latte in hand, head to Lake Ontario’s northern shore. Here, the tiny and welcoming town of Picton is a refuge away from everyday stresses, its less-than-5,000 residents welcoming you to join in the bliss of simple pleasures. As the largest community in Prince Edward County (PEC), the town is a glorious homebase for the county’s 35 wineries, like the Waupoos Estates Winery, which is famous for its ciders, and the Hinterland Wine Company which is best known for its sparkling wines. Other samplings can be explored via the Taste Trail, a self-guided tour of the area’s top wineries, breweries, and restaurants.

If you would prefer to stick to town, Picton’s Main Street is where the buzz is at, with places like 555 Brewing Co serving up unique craft beers and woodfired pizzas. Conveniently, Main Street also hosts the town’s best accommodations, like Loyalist Lofts, or The Manse Boutique Inn. You could definitely devote your entire weekend to exploring this darling part of town, but make sure to leave a little time to visit Sandbanks Provincial Park once it opens for the season on April 26th, 2024. The park has 3 sandy beaches, along with the world’s largest baymouth barrier dune.

Greater Napanee

Around 40 minutes from Picton, Greater Napanee (Napanee, for short) is another adorable community perfect for unwinding and finding beauty in all things simple–but do not mistake simple for boring. Ease into your stay with a walk down Napanee’s busiest strips on Dundas Street and Market Square, where locally owned boutiques like Black Barn Company and coffee houses like Ellena’s Cafe and Pantry will fill your weekend with window shopping and comforting bites. You can even book a stay right downtown in an adorable Town Hall Suite with Airbnb, which is right across from the town’s historic town hall.

Speaking of historic structures, history buffs, and architecture enthusiasts will definitely want to venture on Napanee’s self-guided historic walking tour, which you can find on the municipality’s website. The tour includes gems like the 1864 County Court House, 1888 Napanee Post Office, and The Allan Macpherson House, which dates all the way back to 1826. Nature lovers, on the other hand, will delight in Napanee Falls, a stacked-stone cascade in Springside Park near the Napanee Falls estuary. Picnics and scenic strolls are also highly recommended at Napanee Conservation Park, which is easily reached from Springside Park on a riverside boardwalk.

St. Jacobs

With less than 2,000 locals, some assume the town of St. Jacobs could be missed if you blinked while driving through. But this tiny town is actually a celebrated tourist hub, its heavy foot traffic attributed to its Mennonite heritage, rustic village feel, and unique shopping. The Mennonite Story Interpretive Centre is a great first stop to learn more about the town’s Mennonite history, and downtown shops like Stone Crock Bakery are a great follow-up to sample traditional Mennonite baked goods.

The downtown area is also where you can find a ton of quirky stores you will not find anywhere else. Whether you are in the market for a handcrafted duvet at St. Jacobs Mennonite Quilts, a unique handmade gift from Bliss Artisan Boutique, or even a healthy treat for your four-legged friends at Spoil the Dog Bakery, St. Jacobs’ one-of-a-kind shopping district has it all. But if your shopping bug has you wanting more, you will not want to pass up a visit to Canada’s largest year-round market. The famous St. Jacobs Farmers’ Market has over 250 vendors selling anything from local produce to handcrafted jewelry and everything in between. Book a stay at Hotel 52 right in town for the chance to shop till you drop all weekend long. The adorable 5-room hotel embraces its quaintness, and each room is stylishly themed to suit the vibe you are after.

Final Thoughts

Whether you live in a neighboring small town or one of Ontario’s great megacities, sometimes we all just need a weekend away from the stresses of our everyday lives. Whether that means visiting “The Prettiest Town in Canada” for a weekend of wine tastings and lakeside strolls or an active weekend of hiking and biking in Algonquin Provincial Park with Huntsville as your gateway, the way you spend your weekend retreat is up to you–why not make the best of it?

Published in World Atlas

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