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Trail Running Calendar near Wolcott 2026-2027

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Explore the top trail runs near Wolcott for 2026-2027! We've gathered 29 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

November 2026
Nov
26
Th

Soul N Body Thanksgiving Trail Run

Trail Run Walk 4 mi
A community Thanksgiving trail event on 11/26/2026 at Mill Pond Way Trail with a 3.5 mile run or walk, chip timing, post race yoga for participants, free water and snacks, and proceeds benefiting endometriosis research.
Nov
26
Th

Roxbury Thanksgiving Day Charity Race

Trail Run 5 km
A ninth annual charity 5K in Roxbury, Connecticut on November 26, 2026, with a 3.1 mile out-and-back course near Everett B. Hurlburt Community Park. Proceeds support local ambulance and scholarship funds and a food pantry collection.
December 2026
Dec
5
Sa

Tower Tag Challenge

Trail Run 3 mi
A repeated 3.3 mile out and back on the Tower Trail at Sleeping Giant State Park, with four hour and eight hour options and a cupless aid station at start and finish.
Dec
19
Sa

Frosty Forest 5K

Trail Run Walk 5 km
Experience an exclusive trail run through the scenic Roosevelt Forest in Stratford. This 5K event features a natural off-road course limited to a small group of participants and includes custom finisher medallions.
March 2027
Mar
20
Sa

Enchanted Forest Ultra Run

Trail Run Walk 50 km
A limited-field 6 hour trail ultra at Roosevelt Forest in Stratford CT with a 50K option on a 2.3 mile loop through roots, rocks and rolling hills.
April 2027
Apr
4
Su

Sleeping Giant Trail Runs

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

Trail Run 17 km 50 km
Trail event in Bloomfield CT with 17K and 50K loop courses featuring technical Metacomet Trail single track and rocky forest terrain.
May 2027
May
8
Sa

Camp Mountain Laurel Color Run & Trail Run

Road Race Trail Run 5 km
Camp Mountain Laurel offers a family color run plus a 5K trail run and 5K trail walk at Hamden/North Haven YMCA and New Haven YMCA Youth Center on May 8, 2027; registration opens Feb 19 and first 100 pre-registrants receive a giveaway.
May
15
Sa

Forgotten Forest Ultra Run - Stratford, CT

Backyard Ultra Walk 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.
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