Trail Running Calendar near Waterbury 2026-2027

March 2027

Trail Run 50 km

Six hour timed trail event at Roosevelt Forest in Stratford CT with a 2.3 mile loop, a 50K option, limited field and awards for top mileage.

April 2027

Apr

4

Su

Sleeping Giant Trail Runs

Hamden | 14 mi from Waterbury

Trail Run 25 km 50 km

Trail races on a 25K loop at Sleeping Giant State Park featuring technical singletrack, steep rock scrambles, and an optional second loop for the 50K.

Apr

17

Sa

Traprock 50

Simsbury | 23 mi from Waterbury

Trail Run 17 km 50 km

Looped trail races in Bloomfield CT offering a rocky, mostly single track 50K and a 17K, with cupless policy and a nine hour cutoff for the 50K.

Apr

25

Su

Deer Lake 5 Mile Trail Run & Kids 1 Mile Trail Run

Killingworth | 28 mi from Waterbury

Trail Run 5 mi

Trail races at Deer Lake Outdoor Center in Killingworth CT with an approx 5 mile course, about 500 ft of elevation gain, and a timed 1 mile kids run.

May 2027

May

15

Sa

Camp Mountain Laurel Color Run & Trail Run

Hamden | 14 mi from Waterbury

Road Race Trail Run 5 km

Family Color Run plus a 5K trail run and 5K trail walk at Camp Mountain Laurel in Hamden on May 15, 2027, with pre-registration benefits and on-site registration.

May

15

Sa

Forgotten Forest Ultra Run - Stratford, CT

Stratford | 26 mi from Waterbury

Backyard Ultra 2 mi

A nine hour timed trail ultra on a 2.2 mile loop through Roosevelt Forest in Stratford, CT. Entry is limited to 50 participants and awards go to the runners with the most miles by the race end.

May

22

Sa

Run Ragged Last One Standing

Berlin | 16 mi from Waterbury

Backyard Ultra 3 mi

An elimination loop race on Ragged Mountain in Berlin CT where runners repeat a roughly 3.11 mile loop each hour until one remains; field limited to 55.