Caledon Hills

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TIP: The calendar view displays up to 7 hikes on a day, but often there are more. Click “More events” to see them all.

< 2026 >
September
  • 01
    September 1, 2026

    Waterdown, Smokey Hollow, Great Falls and Grindstone Creek

    9:30 AM-1:00 AM
    09/01/2026
    Sorry, the registration cut-off time for this hike has been reached.
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    Hosting Club: Caledon Hills
    Category: Tuesday Hikers
    Location (Google Maps): Parking Lot at City View Park off of Kerns Rd.

    Hike Leader(s): Ralph Shapiro Click here to contact Hike Leader(s)

    Pace: Medium – 3 to 4 km/hour
    Terrain: Moderate – some hills and/or some poor footing
    Distance: 10 km

    Description

    From City View parking we will hike to Smokey Hollow and the Great Falls. We’ll break at the Falls for a rest and/or optional hike down Grindstone Creek.

  • 03
    September 3, 2026

    Toronto Fall Series Hike 1 of 9

    9:30 AM-2:30 PM
    09/03/2026
    Sorry, the registration cut-off time for this hike has been reached.
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    Hosting Club: Caledon Hills
    Category: End-to-End
    Location (Google Maps): Meet at Boston Mills Road parking. Map 14, southwest of km 48.4

    Hike Leader(s): Nancy Mooney Click here to contact Hike Leader(s)

    Pace: Medium – 3 to 4 km/hour
    Terrain: Easy – mostly flat and usually good footing, Moderate – some hills and/or some poor footing
    Distance: 13.5 km loop

    Description

    This is the first hike of a Toronto End-to-End Series that will also include side trails. Most of the hikes in the series will be loops.

    This hike will take us along the main trail to the Rockside Side Trail then back to Boston Mills Road all the way to the Cheltenham Badlands before a post hike stop at the Spirit Tree Cidery.

  • 06
    September 6, 2026

    The Train Wreck Hike

    9:30 AM-1:00 PM
    09/06/2026
    Sorry, the registration cut-off time for this hike has been reached.
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    Hosting Club: Caledon Hills
    Category: General
    Location (Google Maps): Meet at the roadside parking at the junction of Escarpment Side Road and Willoughby Road, km 15.9 (Map 15).
    Car Pool to roadside parking at Mountain View Side Trail on Mountain View Road. Google Map Coordinates: 43.894254, -79.922522, north of km 26.8 (Map 15).

    Hike Leader(s): Dan Revington Click here to contact Hike Leader(s)

    Pace: Medium – 3 to 4 km/hour
    Terrain: Moderate – some hills and/or some poor footing
    Distance: 10.2 km

    Description

    In September 1907, a passenger train went off the tracks on the steep Horseshoe Valley Curve on the Niagara Escarpment. Seven people were killed and dozens were injured. The Bruce Trail passes close to the location of this disaster. Join us for a hike that includes a stop at the historic St. Andrew’s Stone Church Cemetery, panoramic views from Escarpment Road, and to learn about the tragic story and mystery of the famous Horseshoe Curve Rail Disaster.

    Bring your choice of hydration and snacks. We will be going through the forest, as well as walking on roads. There is one steep hill. Sturdy footwear is essential. Note: this is a car pool hike.

  • 08
    September 8, 2026

    Mono Cliffs, Map 19

    9:30 AM-2:30 PM
    09/08/2026
    Sorry, the registration cut-off time for this hike has been reached.
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    Hosting Club: Caledon Hills
    Category: Tuesday Hikers
    Location (Google Maps): Mono Community Centre Parking, 200 m south of Mono Centre.
    Driving direction: From Highway 410 go north, continue on Highway 10, pass through Orangeville, continue to Mono Centre Rd. (8), turn right, road will merge with 2nd Line EHS north, parking on the right just before Mono Centre.

    Hike Leader(s): Mohammad Shafiq Click here to contact Hike Leader(s)

    Pace: Medium – 3 to 4 km/hour
    Terrain: Moderate – some hills and/or some poor footing
    Distance: 12 km

    Description

    Will hike main Bruce Trail, Walter Tovell, McCarston’s Lake and Lookout Side Trails.
    Bring water, snack, bug spray and sun protection. Poles recommended.
    Hike leaders contact # 416-566-0503

  • 10
    September 10, 2026

    Toronto Fall Series Hike 2 of 9

    9:30 AM-2:30 PM
    09/10/2026
    Sorry, the registration cut-off time for this hike has been reached.
    Not a member? Click here to join today!

    Hosting Club: Caledon Hills
    Category: End-to-End
    Location (Google Maps): Meet at Heritage Road Parking, Map 14, southeast of km 44.6 where the Main Trail meets Heritage Rd.

    Hike Leader(s): Nancy Mooney Click here to contact Hike Leader(s)

    Pace: Medium – 3 to 4 km/hour
    Terrain: Easy – mostly flat and usually good footing, Moderate – some hills and/or some poor footing
    Distance: 14.5 km loop

    Description

    This is the second hike in the series and will take us around Terra Cotta Conservation Area. It will include the Walking Fern and Terra Cotta Side Trails.