Upcoming Races Near Chestertown, MD - Matching: Trail Races

Name: The Kingdom Run 5K
Start: 2026-09-12
End: 2026-09-12
Location: Bel Air

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Grape Stomper Trail Run

Landenberg, PA

Friday, September 19th, 2025

Trail

View details for race Grape Stomper Trail Run

THE Conestoga Trail Run - 10 Tough Miles

Holtwood, PA

Sunday, September 28th, 2025

10 Miles

Trail

View details for race THE Conestoga Trail Run - 10 Tough Miles

Charm City Run 20-Miler

Freeland, MD

Sunday, September 28th, 2025

Ultra

Trail

View details for race Charm City Run 20-Miler

Friends of the Poor 5K Walk/Run & Kiddy-K

Owings, MD

Saturday, October 4th, 2025

Trail

Fast

View details for race Friends of the Poor 5K Walk/Run & Kiddy-K

Kettle Cooker Five & Dime Trail Race

Nottingham, PA

Sunday, October 5th, 2025

10 Miles

Trail

View details for race Kettle Cooker Five & Dime Trail Race

BRRC Fall Long Run/Half Marathon Training Group

Towson, MD

Saturday, October 18th, 2025

Trail

View details for race BRRC Fall Long Run/Half Marathon Training Group

The Husky Run 5K

Bel Air, MD

Sunday, October 19th, 2025

Trail

View details for race The Husky Run 5K

Jurassic Dash 5K & Fun Run

Fallston, MD

Saturday, November 8th, 2025

1 Mile

Trail

View details for race Jurassic Dash 5K & Fun Run

Run Of The Mill 5/10-miler walk/run trail runra...

Wilmington, DE

Saturday, November 15th, 2025

10 Miles

Trail

View details for race Run Of The Mill 5/10-miler walk/run trail runraiser

NCR Marathon & Half Marathon

Sparks Glencoe, MD

Saturday, November 29th, 2025

Marathon

Half

Trail

Fast

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2026 PHUNT 25K/50K TRAIL RACE

Elkton, MD

Saturday, January 17th, 2026

Trail

View details for race 2026 PHUNT 25K/50K TRAIL RACE

Hot Chocolate 5K

Stevensville, MD

Sunday, February 15th, 2026

Trail

View details for race Hot Chocolate 5K

Conquer The Canal

Delaware City, DE

Saturday, May 30th, 2026

Marathon

10K

Trail

View details for race Conquer The Canal

ASICS Independence Day 4-Miler presented by Ind...

Bel Air, MD

Sunday, July 5th, 2026

Trail

View details for race ASICS Independence Day 4-Miler presented by Independent Brewing Company

ASICS Independence Day 4 Miler presented by Ind...

Bel Air, MD

Sunday, July 5th, 2026

Trail

View details for race ASICS Independence Day 4 Miler presented by Independent Brewing Company EARLY BIRD REGISTRATION (2026)

Catch-A-Pig 5K & 1K Bacon Stroll

Bel Air, MD

Sunday, August 16th, 2026

Trail

View details for race Catch-A-Pig 5K & 1K Bacon Stroll

The Kingdom Run 5K

Bel Air, MD

Saturday, September 12th, 2026

Trail

View details for race The Kingdom Run 5K

Explore more in Chestertown, MD

Distances:

5K 10K Half Marathon Marathon

Months:

September October November

Tags:

Trail Boston Qualifiers Fast Courses

State:

All Maryland races

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