Corp Comm Connects

Take a trip to one of these quaint Ontario towns this weekend
Aug. 8, 2017

Size doesn't matter when it comes to choosing the perfect road trip destination, but charm does. In Ontario's York Durham Headwaters region, there's a myriad of pint-sized towns that deliver big appeal.

From local, chef-run restaurants to stunning architecture, there's a lot to love. Find your way to these Instagram-worthy towns you might not have considered before, but will now thanks to our partnership with Ontario Tourism and York Durham Headwaters.


The Village of Erin just might be Ontario's best-kept secret when it comes to charming historic downtown areas. Those who have already discovered it, flock to the village on the west branch of the Credit River to admire its well-preserved Victorian architecture. Visitors also pop into Erin's many unique shops and take on adventures like hiking, cycling and horseback riding amongst its nearby rolling hills.


It may have started out as a small village, but Georgina has grown quickly thanks to its proximity to bigger cities and its recreational offering. This small town is popular amongst cottage lovers, thanks to its gorgeous Lake Simcoe backdrop.

A great option for families is the Georgina Pioneer Village. Kids will have a chance to learn about Canadian history and partake in hands-on activities from the past. For the adults, the town also has a robust live-theatre scene headquartered in the Stephen Leacock Theatre, named after the famed humorist who once called the town home. Catch a show, then head to the Lake Simcoe Arms for authentic British pub grub and a selection of 15 beers on tap.


The scenic countryside of Caledon provides a number of ideal places for an Instagram moment. But before you capture the perfect selfie, check into a welcoming spot like the Millcroft Inn and Spa for some rest and relaxation.

Be sure to visit the Alton Mills Arts Centre where the work of artists and artisans can be discovered in a setting that is a work of art unto itself. Stop by Spirit Tree Estate Cidery where award-winning cider and baked goods make leaving empty-handed nearly impossible. Green thumbs will appreciate the short drive to Plant Paradise Country Gardens for its wealth of blossoms and goods for sale.


This small village is a big player in the arts scene thanks to its star attraction, the McMichael Canadian Art Collection. This is where you'll find the work of the Group of Seven, an all-star lineup of the country's most celebrated artists, as well as First Nations and Inuit art.

Craving a dose of carbs? Kleinburg has several stellar Italian restaurants, including Avenue Cibi E Vini and Villagio Ristorante. After dinner, go for an evening walk through the quaint, historic downtown to enjoy all the wonderfully preserved heritage buildings.


The streets of Unionville have plenty of stories to share, given that the city was founded in 1794. Today, tourism is an important industry, thanks to the city's charming buildings, boutiques, restaurants and coffee shops. It's so picturesque that scenes from the television show, "Gilmore Girls," were filmed on Main Street.

Shoppers will find themselves in a happy place with a wide range of clothing boutiques and shoe stores, plus sweet stops like The Old Firehall Confectionery, featuring freshly made fudge.

Port Perry

This cute-as-a-button town is home to a truly stunning Victorian-era downtown. There are so many beautifully preserved homes and buildings that have been repurposed as art galleries, restaurants, boutiques and bed and breakfasts, making it the perfect place for weekend getaways.

The roster of year round events is also impressive, from dragon boat races and bass fishing competitions on Lake Scugog to a variety of food and arts festivals that take over the historic downtown. Guests have plenty to do, whether it's attending a live performance at the Town Hall 1873 Centre for Performing Arts, boutique shopping, or heading out onto Lake Scugog for some paddling or fishing.