Caledon, Ontario

Looking for the best chillin in Caledon? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Caledon. The detailed guides, photos, and reviews are all submitted by the Outbound community.

Top Chillin Spots in and near Caledon

  • Burlington, Ontario

    Hike the Mount Nemo Conservation Area Loop

    5.0
    1.6 mi
    This is probably one of my all-time favorite short hikes to do in Ontario during the fall. The hikes takes you to a breathtaking, panoramic view of the Niagara Escarpment that is blazed with fall colors. This family-friendly lookout trail should provide a very little challenge for older family me...
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  • Toronto, Ontario

    Ice Skate in the Heart of Toronto

    3.0
    A popular activity during the winter for many locals and tourists alike, ice-skating in Nathan Phillips Square is right of passage for any tourist visiting Toronto. It only costs money to rent skates, the ice-rink is open to the public between November and March, weather permitting. It's a wonder...
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  • Toronto, Ontario

    Berczy Park

    5.0
    One of my favorite parks in Toronto, Berczy Park boasts the most amazing water fountain you’ll ever see in your life. It is purely dedicated to the love of dogs with a token and symbolic gesture, to our other beloved family pet, the cat. Let’s see if you can find them! Berczy Park is named after...
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  • Toronto, Ontario

    Explore Toronto Island

    5.0
    1 mi
    Explore Toronto Island and find yourself in a small island community with amazing views of downtown. Follow the paved pathway that leads past small homes and to a beach on the other side of the island. To get to the island, you'll take the ferry from The Jack Layton Ferry Terminal (the ferry dock...
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  • Hamilton, Ontario

    Photograph Great Falls

    5.0
    0.1 mi
    The perfect little adventure in the city of Hamilton, this waterfall is along the iconic Bruce Trail and can easily be turned into a longer adventure along the Grindstone Creek. It can be explored at any time of the year, whether you're looking for a lot of water in the spring, fall foliage in au...
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  • Burlington, Ontario

    Visit the Royal Botanical Gardens in Burlington

    5.0
    Start at the main building to get your day pass. Then explore the indoor gardens filled with tropical plants. Once finished inside take the underground tunnel to Hendrie Park to enjoy the roses and calm lilly ponds. There are also areas accessible by car: the Rock Garden, Arboretum, and several t...
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  • Hamilton, Ontario

    Hike the Dundas Escarpment

    4.1
    1.9 mi
    Starting at Webster's Falls, this hike continues down the trail to Tews Falls and then leads to the Dundas Peak, with panoramic views of the surrounding towns, Dundas & Hamilton. This is a short hike and totals around 3km. There are some side trails that could be taken to offer variety and ad...
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  • Hamilton, Ontario

    Photograph Webster's Falls

    5.0
    0.25 mi
    The waterfall is located in the Spencer Gorge Conservation Area, which is delightful enough by itself to explore and have a picnic or lounge around. The easiest way to access this area is to park at the lot at the end of Fallsview Rd, located on top of the Dundas escarpment area. There is a $10 f...
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  • Ayr, Ontario

    Hike the Walter Bean Grand River Trail (Section 1-2)

    4.0
    4.3 mi / 100 ft gain
    Start by parking in the lot just off of Highway 42, and check out the trail map. There is a maintained trail perfect for biking or walking, or a forest trail for intermediate walkers. A good way to do this trail is start by heading to the waterfall, then back up and follow the forest trail north ...
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  • Ayr, Ontario

    Walk along the Dumfies Road Trail

    1.9 mi / 10 ft gain
    This little trail is located right of of dumphries rd (parking lot is hidden in some trees, be sure not to miss it). This trail is easy to follow and easy to walk. In the trail you can enjoy the local chickadees and herons while over looking small lakes. The simple walk allows for a bit of relaxa...
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  • Toronto, Ontario

    Hike the Orchard Trail in Rouge Park

    5.0
    1.2 mi
    The Orchard Trail is the most diverse of the trails in Rouge Park. It will take you through the woods, along the Little Rouge Creek, up along the escarpment to enjoy the views, and through some wetlands.The Twyn Rivers parking lot is a great starting point in Rouge Park. To begin the Orchard Trai...
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  • Flesherton, Ontario

    Hike to Eugenia Falls

    0.5 mi / 25 ft gain
    Situated in the very tiny village of Eugenia, Eugenia Falls Conservation Area encompasses 23 hectares of Niagara Escarpment, river valley and upland forests. The site features hiking trails, a picnic pavilion, privies and a war memorial, as well as the 30 metre tall waterfall. When first discover...
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