Date: Saturday & Sunday, October 18–19
Time: 12:00 PM – 4:00 PM on both days
Location: Highlands Art & Tree Trail, Duntroon Highlands Resort
About the Event
Take a Walk on the Wild Side this fall at Duntroon Highlands! Explore the breathtaking Highlands Art & Tree Trail during peak autumn colours while joining a fun and interactive Scavenger Hunt. Along the 2 km loop you’ll discover art installations, tree-inspired creations, and the natural beauty of the Escarpment—while searching for 12 hidden items.
This is a new, family-friendly event open to everyone. Walk the trail at your own pace, record your answers the old-fashioned way—on a piece of paper—and enjoy the season’s colours in a whole new way. For everyone’s enjoyment and safety, please do not bring dogs.
Registration & Prizes
Trail access and scavenger hunt participation are free for all. Donations to the art trail are always welcome however
To be eligible for prizes, pre-register online for just $10 per team or individual.
Pre-registered participants who answer all 12 questions correctly will be win prizes from local stores, gift cards to Duntroon Highlands Resort, jars of local Highlands Honey and more!
How it Works
1. Come up to Duntroon Highlands and check-in at the store in the Clubhouse main building.
2. You’ll get your scavenger hunt clue card to help you find the 12 riddles + map of the Highlands Art & Tree Trail. You can also sign the activity waiver then or do it NOW.
3. Head out onto the Highlands Art & Tree Trail. All the clues are on the trail.
4. It takes about 1 hour to walk the Highlands Art & Tree Trail. More information about the trail HERE. Please do not bring dogs.
5. Once you’ve come back to the Clubhouse, hand in your clue card with your answers. If you get all 12 riddles correct, you win a prize right there and then!
6. Even if you do not solve all 12 riddles, please come say hello in the store so we know that you are safely off the trail.
Teams Encouraged
Bring your family, friends, or co-workers and form a team—it makes the scavenger hunt even more fun! Every pre-registered participant or team who answer the 12 riddles/challenges successfully will be eligible for prizes.
Food, Drink & Relaxation
Before or after your walk, visit the Highlands Café at the Clubhouse. From hearty meals to light snacks, coffee, and local beverages, it’s the perfect spot to recharge, share laughs, and compare scavenger hunt finds.
Make It a Weekend
There’s lots to do in Simcoe County in September. Check out all the things to do!
Stay & Explore
We can recommend several great places to stay for the weekend. Check out our accommodation partners HERE.
Why Join?
The Walk on the Wild Side is more than a scavenger hunt—it’s a chance to:
> Spend quality time outdoors with family and friends
> Enjoy brilliant fall colours on the Niagara Escarpment
> Support the ongoing development of the Highlands Art & Tree Trail through your registration
> Experience a shoulder-season activity that celebrates nature, art, and community
Pre-register now for $10 to secure your spot and be eligible for prizes!
Donations to the Art Trail are also welcome and can be made upon checkin at the store at Duntroon Highlands.
