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Upcoming Races Near Middletown, CT - Matching: Trail Races

Ivoryton Pumpkin Chase

Ivoryton, CT

Saturday, October 18th, 2025

Featured

5K

Trail

View details for race Ivoryton Pumpkin Chase

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Tom Centinaro Memorial "Dam" Race

Wolcott, CT

Saturday, October 18th, 2025

Trail

View details for race Tom Centinaro Memorial "Dam" Race

Haunted Hustle

Waterford, CT

Sunday, October 26th, 2025

5K

1 Mile

Trail

View details for race Haunted Hustle

RACE FOR THE GREENWAY 5K RUN / WALK

Riverhead, NY

Sunday, October 26th, 2025

Trail

View details for race RACE FOR THE GREENWAY 5K RUN / WALK

Stonington Vineyards Wine Run Turkey Trot 5k

Stonington, CT

Sunday, November 2nd, 2025

5K

Trail

View details for race Stonington Vineyards Wine Run Turkey Trot 5k

Centerville Bank Thompson Turkey Trot

Thompson, CT

Sunday, November 9th, 2025

5K

Trail

View details for race Centerville Bank Thompson Turkey Trot

The Witching Hours 3/6/12H

Manorville, NY

Saturday, November 15th, 2025

Trail

View details for race The Witching Hours 3/6/12H

BROOKHAVEN TRAIL HALF MARATHON and 5 MILE

Wading River, NY

Sunday, November 16th, 2025

Half

Trail

View details for race BROOKHAVEN TRAIL HALF MARATHON and 5 MILE

JINGLE BELL JOG 5K AND RUDOLPH'S FUN RUN

Calverton, NY

Saturday, December 6th, 2025

Trail

View details for race JINGLE BELL JOG 5K AND RUDOLPH'S FUN RUN

Ion Bank Cheshire Road Races

Cheshire, CT

Sunday, April 12th, 2026

Half

5K

Trail

Fast

View details for race Ion Bank Cheshire Road Races

Run the Vineyards - Memorial Day at Pindar 5K

Peconic, NY

Sunday, May 24th, 2026

5K

1 Mile

Trail

View details for race Run the Vineyards - Memorial Day at Pindar 5K

IronHike Endurance Series - Spring 2026 - Mohaw...

Cornwall, CT

Wednesday, June 3rd, 2026

Ultra

Trail

View details for race IronHike Endurance Series - Spring 2026 - Mohawk Mtn, CT, USA

IronHike Series - Spring '26

Mohawk Mtn Ski Area, Cornwall, CT

Thursday, June 4th, 2026

Ultra

Trail

View details for race IronHike Series - Spring '26

Iron Hike - Spring Kuwohi Trail Half Marathon P...

Cornwall, CT

Saturday, June 6th, 2026

Trail

View details for race Iron Hike - Spring Kuwohi Trail Half Marathon Plus - 15 Miles | 7,140' Elevation | 12-Hour | Run, Hike or Walk

Run the Vineyards - Pindar Vineyards 5K

Peconic, NY

Sunday, July 26th, 2026

5K

Trail

View details for race Run the Vineyards - Pindar Vineyards 5K

Run for The Hills

Niantic, CT

Saturday, September 12th, 2026

5K

Trail

View details for race Run for The Hills

Explore more in Middletown, CT

Distances:

5K 10K Half Marathon Marathon

Months:

October November December

Tags:

Trail Boston Qualifiers Fast Courses

State:

All Connecticut races

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