The Fifteen Most Charming Towns in Ontario

The Fifteen Most Charming Towns in Ontario

The Fifteen Most Charming Towns in Ontario

Captivating Beauty and Authentic Charm:
Exploring Ontario's Top 15 Charming Towns

When it comes to appreciating the charm of Ontario's small towns, Guess Where Trips has got you covered. Our journeys frequently feature, or end in, delightful and enchanting small towns, where you can choose your own adventures as the day winds down. Below, we have compiled a list of our most beloved charming towns, located just a short distance away from fast-paced city life. With their historical architecture, natural landscapes, and genuine hospitality, each town is  both bursting with beauty and warmth. 

Reader be warned: we've carefully hidden the trips featuring these charming small towns, but clicking on the links will reveal them instantly. If you prefer to keep our trips a surprise, we highly advise that you do not click on the links. However, for those who are eager to uncover these hidden gems, the links will guide you directly to the trips where you can find these towns. The choice is yours – embrace the element of surprise, or embark on a journey of discovery.

Niagara on the Lake, Stratford, Elora


Nestled along the shores of Lake Ontario, Niagara-on-the-Lake is renowned for its elegant 19th-century architecture, charming boutiques, and lush vineyards. Take a leisurely stroll down Queen Street, explore the historic Fort George, and indulge in world-class wines at the local wineries. You can find Niagara-on-the-Lake on this itinerary.


Famous for its annual Stratford Festival, this town is a haven for theatre enthusiasts. With its quaint downtown lined with shops and cafes, Stratford exudes a classic small-town charm. Don't forget to visit the beautifully manicured gardens along the Avon River. Stratford is a stop on two of our itineraries: this one for beer loves, and this one for those looking for a relaxing day out.


Elora enchants visitors with its stunning natural beauty and charming architecture. Discover the Elora Gorge, a breathtaking conservation area, and explore the town's vibrant arts scene, featuring galleries, studios, and an annual folk festival. You can find it on our best selling trip here.

Bayfield, Creemore, Picton


Situated on the shores of Lake Huron, Bayfield is a charming coastal town known for its tranquil beaches and scenic harbour. Stroll through the downtown core, browse unique boutiques, and savour fresh seafood at one of the town's cozy restaurants. We have a great trip that ends in Bayfield here


Tucked away in the heart of Ontario's countryside, Creemore is a delightful town steeped in history and charm. Explore the quaint streets lined with heritage buildings, visit the renowned Creemore Springs Brewery, and enjoy the serene beauty of the surrounding rolling hills. Find this famous beer town on this trip.


As the gateway to Prince Edward County, Picton offers a delightful blend of small-town charm and natural beauty. Discover the vibrant Main Street with its boutique shops and art galleries, explore the Macaulay Heritage Park, and embark on a scenic boat tour along the bay. Treat yourself to a weekend away in the hottest wine county in Ontario on this trip.

Goderich, Almonte, Perth


Located on the shores of Lake Huron, Goderich is often referred to as "Canada's prettiest town." Marvel at the town's impressive octagonal square, relax on the sandy beaches, and soak up the serene ambiance of this lakeside gem. Queen Elizabeth's favourite Canadian town can be found on this trip.


On the banks of the Mississippi River, Almonte is a picturesque town known for its historic mills and lively arts community. Visit the Mississippi Valley Textile Museum, stroll through the charming downtown, and witness the town's scenic beauty at the nearby Mill of Kintail Conservation Area. Visit this charming town on this beer-lovers trip here.


Perth is a hidden gem known for its rich history and charming architecture. Explore the town's historic core with well-preserved stone buildings, visit the Perth Museum to learn about its past, and enjoy the peacefulness of Stewart Park along the Tay River. Find it on this Ottawa-area trip

Bala, Belfountain, Paris


Located in the heart of Muskoka, Bala is a picturesque town known for its stunning natural beauty and charming waterfront. Explore the scenic Bala Falls, enjoy a leisurely boat ride on Lake Muskoka, and immerse yourself in the town's rich musical heritage at the famous Kee to Bala concert venue. This cottage-country town can be found on this itinerary.


In the picturesque Caledon Hills, Belfountain is a hidden gem known for its natural beauty and quaint village charm. Explore the Belfountain Conservation Area with its stunning waterfall and hiking trails, admire the historic stone houses that line the streets, and visit the quaint shops and cafes in the village. Belfountain offers a serene retreat for nature lovers and those seeking a peaceful escape from city life, and can be found on this Guess Where Trips itinerary.


Paris is often referred to as the "Prettiest Little Town in Canada" (not to be confused with Goderich's "prettiest town" moniker). Its charming cobblestone streets, historic buildings, and beautiful parks make it a delightful destination. Take a stroll across the picturesque Arlington Bridge, explore the Paris Museum and Historical Society, and enjoy a scenic paddleboat cruise along the Grand River. With its small-town charm and scenic riverside setting, Paris captures the hearts of visitors with ease and can be found on this trip.

Blue Mountain, Thornbury, Merrickville

Collingwood & Blue Mountain

Situated on the shores of Georgian Bay, Collingwood is a delightful town that offers a mix of natural beauty and vibrant urban amenities. Explore the picturesque waterfront, visit the charming downtown shops and eateries, and take in stunning views from the top of Blue Mountain. The town of Blue Mountain itself offers a unique blend of outdoor adventure and cozy village charm, just 10 minutes from Collingwood. Enjoy skiing and snowboarding in the winter, hiking and mountain biking in the summer, and explore the village's shops, restaurants, and lively events throughout the year. Find these iconic towns at the end of this trip.


Located in the heart of Ontario's apple country, Thornbury is a picturesque town known for its orchards, wineries, and scenic waterfront. Explore the charming downtown, indulge in local cider tastings, and take in the breathtaking views of Georgian Bay. This town is one of two optional endings on this itinerary.


Known as the "Jewel of the Rideau," Merrickville is a charming town located along the historic Rideau Canal. Discover its well-preserved Victorian architecture, browse through boutique shops and art galleries, and take a scenic boat ride along the canal. Find this jewel halfway through this trip.


Ontario's charming towns offer an escape from the hustle and bustle of city life, providing a glimpse into the province's rich history, natural wonders, and warm hospitality. Whether you're seeking cultural experiences, outdoor adventures, or simply a tranquil retreat, these fifteen towns will leave an indelible impression on your heart. Prepare to be captivated by their quaint streets, embraced by the friendliness of the locals, and enveloped in an atmosphere that feels like a warm embrace.


Photo sources: Elora, Bayfield, Picton, Goderich, Almonte, Perth, Bala, Belfountain, Blue Mountain, Merrickville

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