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Upcoming Races Near Chestertown, MD - Matching: Trail Races

Earth Day 5K

Bel Air, MD

Wednesday, April 22nd, 2026

Featured

5K

1 Mile

Trail

View details for race Earth Day 5K

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Be You 5K Run/Walk

Glenn Dale, MD

Saturday, May 16th, 2026

5K

Trail

View details for race Be You 5K Run/Walk

Conestoga Crusher 5K & 10k Trail Race & Kids Tr...

Holtwood, PA

Saturday, May 16th, 2026

10K

5K

1 Mile

Trail

View details for race Conestoga Crusher 5K & 10k Trail Race & Kids Trail Race

Catch Me If You Can 5K

Bel Air, MD

Saturday, May 16th, 2026

5K

1 Mile

Trail

View details for race Catch Me If You Can 5K

First State Trail Race

Wilmington, DE

Sunday, May 17th, 2026

10K

Ultra

Trail

View details for race First State Trail Race

Dawn's 5k Dash

Fallston, MD

Sunday, May 17th, 2026

5K

Trail

View details for race Dawn's 5k Dash

Conquer The Canal

Delaware City, DE

Saturday, May 30th, 2026

Marathon

5K

10K

Trail

View details for race Conquer The Canal

Miles of Music 5K

Bel Air, MD

Saturday, June 20th, 2026

5K

1 Mile

Trail

View details for race Miles of Music 5K

Run the Vineyards - Harvest Ridge Winery 5K

Marydel, DE

Saturday, June 20th, 2026

5K

Trail

View details for race Run the Vineyards - Harvest Ridge Winery 5K

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)

Run the Vineyards Bohemia Manor Farm 5K & 8K

Chesapeake City, MD

Saturday, August 1st, 2026

5K

Trail

View details for race Run the Vineyards Bohemia Manor Farm 5K & 8K

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

Bel Air, MD

Sunday, August 16th, 2026

5K

Trail

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

The Kingdom Run 5K

Bel Air, MD

Saturday, September 12th, 2026

5K

Trail

View details for race The Kingdom Run 5K

Great Human Race 5K

Newark, DE

Sunday, September 13th, 2026

5K

Trail

View details for race Great Human Race 5K

Charm City Run 20-Miler

Freeland, MD

Sunday, September 27th, 2026

Ultra

Trail

View details for race Charm City Run 20-Miler

THE Conestoga Trail Run - 10 Tough Miles

Holtwood, PA

Sunday, September 27th, 2026

10 Miles

Trail

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

Kettle Cooker Trail Race

Nottingham, PA

Sunday, October 4th, 2026

Ultra

Trail

View details for race Kettle Cooker Trail Race

Naptown Half Marathon & 10K/5K

Annapolis, MD

Saturday, December 19th, 2026

Half

10K

5K

Trail

View details for race Naptown Half Marathon & 10K/5K

PHUNT 25K/50K TRAIL RACE

Elkton, MD

Saturday, January 16th, 2027

Trail

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

Explore more in Chestertown, MD

Distances:

5K 10K Half Marathon Marathon

Months:

Tags:

Trail Boston Qualifiers Fast Courses

State:

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