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  • Writer's pictureKrista the Explorer

Unique Ontario Experiences You Can't Miss

Updated: Feb 23

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When visitors think of Ontario, places such as Ottawa, Toronto, and Niagara Falls instantly come to mind. And while those are very popular places to go in Ontario, Canada’s most populated province has so much more to offer. The best way to explore Ontario is by car so that you can travel outside of the big cities and see what some of the small towns in Ontario have to offer as well as what hidden gems are dotted around the countryside. Whatever your interests are, Ontario definitely has something for everyone.

There are many unique Ontario experiences to be had but some of these are dependent on what season you’re planning on exploring the province during. My favourite time of the year to travel is in the autumn and Ontario features some of the most beautiful fall foliage in North America so it’s always a great time for a road trip. During my recent trip home we visited a number of destinations in Ontario a little off the beaten path so here’s a look at my top picks for the most unique Ontario experiences you shouldn’t miss.

Unique Ontario Experiences

Ride on a glass bottom boat in Tobermory

A yellow painted boat cruising through blue waters of lake.
Bruce Anchor Cruises

Tobermory sits at the northern tip of the Bruce Peninsula and is home to the Fathom Five National Marine Park. It’s one of the best places to visit in Ontario during the summertime when visitors can enjoy the hiking trails and scuba dive to some historic shipwrecks. We visited at the end of September, when the busy season was coming to a close, but we were just in time to hop on one of the last glass bottom cruises with Bruce Anchor Cruises. It’s a phenomenal experience where you can see directly under the water from inside the boat and even catch a glimpse of one of the shipwrecks from a unique perspective. You also have the option of disembarking at Flowerpot Island which is a popular place to go for nature enthusiasts.

Their cruises run from May - September/early October depending on the weather. The journey lasts just over an hour if you book the stay aboard cruise.

Large motel room with balcony and double bed.
Bruce Anchor Motel

Looking for somewhere to stay in Tobermory? The Bruce Anchor Motel is a great option that’s located across the road from the main dock of Bruce Anchor Cruises. They have a good selection of room types available with modern furnishings as well as balconies if you’re on the upper level. For more space I would recommend booking the king room which also features a mini fridge, a coffee machine, and a TV.

Savour & Sip Trail in Stratford

Selection of food laid out on picnic bench in Stratford.
Savour & Sip Trail

There are a lot of things to do in Stratford, Ontario besides visiting the Festival Theatre, and as a local I can honestly say that a very fun way to explore the city is to purchase tickets for the Savour & Sip Trail. This self-guided tour will take you on a culinary journey where you can choose 6 local businesses to visit from a preselected list and pick up something to either eat or drink. If the weather happens to be favourable you can enjoy your goodies on one of the many picnic benches around the river.

The trail runs until October 31st but there are other options available on the website such as the Bacon & Ale Trail or the Chocolate Trail - both are equally as enjoyable!

Visit a seasonal farm

Farm shop with hundreds of pumpkins decorating the outside.
Fall Harvest Farm

One of the many things I love about exploring Ontario in the autumn is the variety of seasonal farms that you can visit. We stopped by a number of farms around Perth County and the Kitchener-Waterloo region but two that really stood out were Downey’s Apple Farm where you can pick your own apples as well as pumpkins and the Fall Harvest Farm which has a unique theme every year and features hundreds of different types and colours of pumpkins. And of course unique Ontario experiences don’t come much better than the Wellesley Apple Butter & Cheese Festival which takes place on the last Saturday of September every year.

Shale Ridge Estate Winery & Cidery

Wine lovers who visit Ontario automatically head to Niagara-on-the-Lake to visit one of the many vineyards there - and for good reason. However, while we were exploring Ontario’s West Coast we came across Shale Ridge Estate Winery & Cidery which is a fantastic alternative to NOTL and is a one-of-a-kind experience in Ontario. This winery is unlike any you’ll have come across, with stunning views over the countryside, tasty food to pair with your wine, and some very unique seating options to enhance the experience.

Located a short drive from Grand Bend, Shale Ridge Estate Winery & Cidery offers visitors a fun wine tasting experience (or cider if you prefer) where you’ll sample 4 different wines all while sitting on one of their unique swing tables! You can of course choose another style of seating but this is the most unique option. They also feature a food menu of pinsas and a delicious charcuterie board which are all great for sharing. And before you go don’t forget to stop by their shop so you can take your favourite wine home with you!

Hop on a heritage train

Heritage train parked at small station in St Jacobs, Ontario.
Waterloo Central Railway

Have you ever travelled on a heritage train? The Waterloo Central Railway runs a heritage hopper service that takes you through Woolwich County and parts of Waterloo Region that are locally known as Mennonite farm country. We hopped on at the St Jacobs Farmers Market station after walking around Canada’s largest year-round farmers market but there are two other stops available to join the route from. It’s an historic railway line that’s been in operation since the 1880s so it’s a very unique Ontario experience to have. The route takes just under 2 hours and isn’t overly scenic but sitting in the train carriage makes you feel like you’ve stepped back in time.

Indulge in a traditional afternoon tea at RoyalTea on King

Three tiered afternoon tea setup with vintage tea cups.
Afternoon tea

A trip up north to Midland, Ontario should be on everyone’s itinerary and we happened to stumble upon the perfect way to spend a couple of hours in the afternoon. RoyalTea on King is a popular spot in downtown Midland for traditional afternoon tea - done the British way. All of their baked goods are freshly made and their homemade scones are some of the best you’ll ever taste. The 3-tiered afternoon tea features finger sandwiches, scones, quiche, and other sweet treats all tied together with a pot of loose-leaf tea of your choosing. The tea room itself is decorated with antique furnishings that really make it feel like you’re in a British tea room and not in Ontario!

Pumpkins After Dark

Tunnel made out of carved pumpkins on dirt trail.
Pumpkins After Dark Milton

Pumpkins After Dark is located in Milton, Ontario and as you will have already guessed this is one of the best things to do in Ontario in the fall/autumn time. This very unique experience in Ontario features over 10000 hand-carved pumpkins and is a self-guided walkthrough that should take you no more than 90 minutes to complete. In 2023 the event featured an indoor “spookeasy” where you could grab something to drink and look at the pumpkin carvers in action. This is a seasonal event that runs every year and tickets cost around $21.95 CAD.

Whether you live in Ontario or are just visiting, the next time you’re looking for something to do I would suggest skipping the regular tourist attractions in Ontario and find something more off the beaten path. There are a lot of fun things to do in Ontario regardless of what time of the year you visit and with a bit of research beforehand you should have no issues filling your itinerary.

Do you know of any more unique Ontario experiences that should be added to this list or have some questions? Please feel free to get in touch via email or Instagram and I’d be happy to chat with you and answer your queries.


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