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Lace up your trail shoes, leash up your dog, and breathe in the crisp autumn air as you explore Steep Rock’s breathtaking preserves. Immerse yourself in the stunning fall foliage while boosting your health and wellness with this ultimate hiking challenge.
We invite you to conquer the highest peaks in Steep Rock’s three iconic preserves:
• The Summit at Steep Rock: Don’t miss the renovated River’s Edge (Goat) Trail—its fresh look, paired with views of the Shepaug River, is nothing short of spectacular!
• The Pinnacle at Hidden Valley: Snap a selfie or two on the famous Thoreau Bridge. It’s especially beautiful during the fall season!
• Waramaug’s Rock at Macricostas: Hike the Boulder’s Trail and soak in the stunning views from this special spot.
Here’s the best part: Complete all three hikes between September 28 and October 19, and you’ll be entered to win exciting prizes!
Who Can Participate?
Everyone is welcome—whether you’re an experienced hiker or a casual nature lover. This challenge is perfect for all ages and fitness levels. Participation is free, though donations to support our trails are always appreciated.
How to Enter:
To qualify for prizes, simply post photos from your hikes on social media using the hashtag #3peaks3weeksSRA AND email photos to info@steeprockassoc.org by October 31, 2025. Winners will be announced in early November.
Trail Maps:
Steep Rock Preserve Trail Map
Hidden Valley Preserve Trail Map
Macricostas Preserve Trail Map
For detailed information about the Challenge and each preserve, click here.
1st Prize
Limited Edition 3 Peaks Hoodie
2nd Prize
Limited Edition 3 Peaks T-Shirt
3rd Prize
Limited Edition 3 Peaks Cozy Mug
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