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Singletracks of Rockland | Madison, CT

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Sky’s the Limit Hiking and Walking Challenge‍ ‍

Sky’s the Limit Hiking and Walking Challenge continues through the summer (April 16–December 4, 2026), with 20 hikes and activities at state parks and forests statewide. Top 100 participants are entered to win a hand carved walking stick‍.

Blue Blazed Hiking Trails Challenge‍ ‍Ongoing!  Hike at your own pace!  You can complete any of the challenge categories in a single season or across your entire hiking lifetime. Earn prizes for distances completed. ‍

October 2 8th Annual CT Trail Symposium Southern Connecticut State University, New Haven. This year’s theme " Benefits of Greenways"

October 3 10AM First Saturday Walk, New Haven Meet at the Canal Dock Boathouse, 475 Long Wharf Drive. We will walk north along the coast towards Water Street and Wooster Square along urban sidewalks, highlighting existing and future trail development, and connections to other urban trails and shoreline east connections.

October 4th 5th Annual SGT 30 Bike Tour. Shoreline Greenway Trail.  Meet in New Haven at Union station and ride to Madison along the beautiful 30-mile Shoreline Greenway Trail. Look for event sign up and details shortly.  

Sunday October 11th 8AM The Nutmeg 40 Pick your pace; make it a Race or just a Ramble. Online Registration Deadline: Thursday, Oct 8, 2026, at 8:00 PM ET. Total Event Registration Limit: 250