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Upcoming Races Near Bridgeport, CT - Matching: Trail Races

ROB'S TRAIL RUN EDITION

Woodbury, NY

Sunday, November 30th, 2025

Featured

Trail

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Woodburrr (no Y) 1-Miler

Woodbury, CT

Saturday, December 6th, 2025

1 Mile

Trail

View details for race Woodburrr (no Y) 1-Miler

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

Tough Cookie 8K Trail Race

Kings Park, NY

Sunday, December 7th, 2025

Trail

Fast

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SRC Presents: A Backyard Ultra

Hauppauge, NY

Saturday, December 13th, 2025

Trail

View details for race SRC Presents: A Backyard Ultra

King of The Hill

Kings Park, NY

Saturday, March 7th, 2026

Trail

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John Jay Community Trail Race

Cross River, NY

Sunday, April 12th, 2026

5K

Trail

View details for race John Jay Community Trail Race

Ion Bank Cheshire Road Races

Cheshire, CT

Sunday, April 12th, 2026

Half

5K

Trail

Fast

View details for race Ion Bank Cheshire Road Races

2026 Deer Lake 5 Mile Trail Run

Killingworth, CT

Sunday, April 26th, 2026

Trail

View details for race 2026 Deer Lake 5 Mile Trail Run

Leatherman's Loop

Cross River, NY

Sunday, April 26th, 2026

10K

Trail

View details for race Leatherman's Loop

Mount Archer Trail Race

Lyme, CT

Sunday, May 3rd, 2026

5K

Trail

Fast

View details for race Mount Archer Trail Race

Spring Run The Farm

Katonah, NY

Sunday, May 17th, 2026

1 Mile

Trail

View details for race Spring Run The Farm

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

Oh Boy 5K

Waterbury, CT

Monday, May 25th, 2026

5K

Trail

Fast

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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

Interstate 17

Closter, NJ

Saturday, August 8th, 2026

Trail

View details for race Interstate 17

South Nyack 10-Miler

Nyack, NY

Saturday, September 5th, 2026

10 Miles

Trail

View details for race South Nyack 10-Miler

IronHike Series - Fall '26

Mohawk Mtn Ski Area, Cornwall, CT

Thursday, October 1st, 2026

Ultra

Trail

View details for race IronHike Series - Fall '26

FALL Run The Farm

Katonah, NY

Sunday, October 25th, 2026

1 Mile

Trail

View details for race FALL Run The Farm

Explore more in Bridgeport, CT

Distances:

5K 10K Half Marathon Marathon

Months:

November December January

Tags:

Trail Boston Qualifiers Fast Courses

State:

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