Upcoming Races Near Chestertown, MD - Matching: Trail Races

Organize a race? Get it in front of thousands of runners.

Add it free Feature it

The Husky Run 5K # 3

Bel Air, MD

Sunday, June 14th, 2026

Featured

Trail

View details for race The Husky Run 5K # 3

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

Miles of Music 5K

Bel Air, MD

Saturday, June 20th, 2026

1 Mile

Trail

View details for race Miles of Music 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 EARLY BIRD REGISTRATION (2026)

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

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

The Peake Run- Our Big Ducking 60th Anniversary...

Annapolis, MD

Sunday, September 13th, 2026

10K

1 Mile

Trail

Fast

View details for race The Peake Run- Our Big Ducking 60th Anniversary Run at the Maryland Seafood Festival

Great Human Race 5K

Newark, DE

Sunday, September 13th, 2026

Trail

View details for race Great Human Race 5K

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

Charm City Run 20-Miler

Freeland, MD

Sunday, September 27th, 2026

Ultra

Trail

View details for race Charm City Run 20-Miler

Kettle Cooker Trail Race

Nottingham, PA

Sunday, October 4th, 2026

Ultra

Trail

View details for race Kettle Cooker Trail Race

NCR Marathon & Half Marathon

Sparks Glencoe, MD

Saturday, November 28th, 2026

Marathon

Half

Trail

View details for race NCR Marathon & Half Marathon

Stocking Suffer 8-Hour Endruance Run

Stevensville, MD

Sunday, December 6th, 2026

Trail

View details for race Stocking Suffer 8-Hour Endruance Run

Naptown Half Marathon & 10K/5K

Annapolis, MD

Saturday, December 19th, 2026

Half

10K

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

Turtle Derby 5k Trail Race

Havre De Grace, MD

Saturday, April 10th, 2027

Trail

View details for race Turtle Derby 5k Trail Race

Explore more in Chestertown, MD

Jump straight to races by distance, month, or type.

Distance

5K 10K Half Marathon Marathon

Month

June July August

Race type

Trail Boston Qualifiers Fast Courses

Nearby

All Maryland races