Upcoming Races Near Chestertown, MD - Matching: Trail Races

Name: Charm City Run 20-Miler
Start: 2026-09-27
End: 2026-09-27
Location: Freeland

Naptown Half Marathon & 10K/5K

Annapolis, MD

Saturday, December 20th, 2025

Featured

Half

10K

Trail

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

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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

Little Patuxent River Half Marathon, 10K & 5K

Columbia, MD

Saturday, January 31st, 2026

10K

1 Mile

Trail

View details for race Little Patuxent River Half Marathon, 10K & 5K

Hot Chocolate 5K

Stevensville, MD

Sunday, February 15th, 2026

Trail

View details for race Hot Chocolate 5K

Springburst 10K & Kids One-Mile Fun Run

Glenn Dale, MD

Saturday, April 18th, 2026

10K

1 Mile

Trail

View details for race Springburst 10K & Kids One-Mile Fun Run

Catch Me If You Can 5K

Bel Air, MD

Saturday, May 16th, 2026

1 Mile

Trail

View details for race Catch Me If You Can 5K

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

Holtwood, PA

Saturday, May 16th, 2026

10K

1 Mile

Trail

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

Conquer The Canal

Delaware City, DE

Saturday, May 30th, 2026

Marathon

10K

Trail

View details for race Conquer The Canal

Run the Vineyards - Harvest Ridge Winery 5K

Marydel, DE

Saturday, June 20th, 2026

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

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

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

Charm City Run 20-Miler

Freeland, MD

Sunday, September 27th, 2026

Ultra

Trail

View details for race Charm City Run 20-Miler

Explore more in Chestertown, MD

Distances:

5K 10K Half Marathon Marathon

Months:

December January February

Tags:

Trail Boston Qualifiers Fast Courses

State:

All Maryland races

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