Upcoming Races Near Windsor Mill, MD - Matching: Trail Races

Name: Naptown Half Marathon & 10K/5K
Start: 2026-12-19
End: 2026-12-19
Location: Annapolis

Earth Day 5K

Bel Air, MD

Wednesday, April 22nd, 2026

Featured

1 Mile

Trail

View details for race Earth Day 5K

Want to feature your race?

Get your race seen first by thousands of runners

Learn More

Learn how to feature your race

Run the Rock | Leesburg

Ashburn, VA

Saturday, April 25th, 2026

Trail

View details for race Run the Rock | Leesburg

23rd annual Potomac River Run Marathon & Half

Washington, DC

Saturday, May 2nd, 2026

Half

Trail

View details for race 23rd annual Potomac River Run Marathon & Half

Healthy Strides 5K 10K

Fairfax Station, VA

Saturday, May 2nd, 2026

10K

Trail

View details for race Healthy Strides 5K 10K

Fountainhead Half Marathon and 10K++ Trail Run

Fairfax Station, VA

Sunday, May 3rd, 2026

10K

Half

Trail

View details for race Fountainhead Half Marathon and 10K++ Trail Run

York Marathon and Half Marathon

York, PA

Sunday, May 3rd, 2026

Marathon

Half

Trail

Fast

View details for race York Marathon and Half Marathon

Be You 5K Run/Walk

Glenn Dale, MD

Saturday, May 16th, 2026

Trail

View details for race Be You 5K Run/Walk

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

Dawn's 5k Dash

Fallston, MD

Sunday, May 17th, 2026

Trail

View details for race Dawn's 5k Dash

WRRC Twilight Series

Westminster, MD

Thursday, May 28th, 2026

Trail

View details for race WRRC Twilight Series

DC Front Runners Pride Run 5K

Washington, DC

Saturday, May 30th, 2026

Trail

View details for race DC Front Runners Pride Run 5K

2025 Girls on the Run Spring 5K - Frederick County

Frederick, MD

Sunday, May 31st, 2026

Trail

View details for race 2025 Girls on the Run Spring 5K - Frederick County

Love, KK - Annual 5KK Race

Leesburg, VA

Saturday, June 6th, 2026

Trail

View details for race Love, KK - Annual 5KK Race

Twilight Series #2 - Hashawha 3 Mile Trail Run

Westminster, MD

Thursday, June 11th, 2026

Trail

View details for race Twilight Series #2 - Hashawha 3 Mile Trail Run

Miles of Music 5K

Bel Air, MD

Saturday, June 20th, 2026

1 Mile

Trail

View details for race Miles of Music 5K

Blue Crab Bolt Trail Run - Seneca Creek

Gaithersburg, MD

Saturday, June 27th, 2026

Trail

View details for race Blue Crab Bolt Trail Run - Seneca Creek

FSRC Independence 5000

Frederick, MD

Saturday, July 4th, 2026

Trail

View details for race FSRC Independence 5000

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

Blue Crab Bolt Trail Run - Schaeffer Farms

Germantown, MD

Saturday, July 25th, 2026

Trail

Fast

View details for race Blue Crab Bolt Trail Run - Schaeffer Farms

Tommy Laudani Delone Dash 5K/3K Trail Run

Hanover, PA

Saturday, August 1st, 2026

Trail

View details for race Tommy Laudani Delone Dash 5K/3K Trail Run

Blue Crab Bolt Trail Run - Little Bennett

Clarksburg, MD

Saturday, August 1st, 2026

10K

Trail

View details for race Blue Crab Bolt Trail Run - Little Bennett

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

Othello Park Labor Day 1K/5k

Knoxville, MD

Monday, September 7th, 2026

Trail

View details for race Othello Park Labor Day 1K/5k

The Kingdom Run 5K

Bel Air, MD

Saturday, September 12th, 2026

Trail

View details for race The Kingdom Run 5K

Sasquatch Preservation Trail Run 5 & 10 K

Seven Valleys, PA

Saturday, September 12th, 2026

10K

Trail

View details for race Sasquatch Preservation Trail Run 5 & 10 K

River's Edge Endurance Challenge

Brunswick, MD

Saturday, September 26th, 2026

Trail

View details for race River's Edge Endurance Challenge

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 Five & Dime Trail Race

Nottingham, PA

Sunday, October 4th, 2026

10 Miles

Ultra

Trail

View details for race Kettle Cooker Five & Dime Trail Race

Rick O'Donnell Memorial 5 Mile Trail Run and Ul...

Mount Airy, MD

Sunday, October 11th, 2026

Trail

View details for race Rick O'Donnell Memorial 5 Mile Trail Run and Ultra Challenge

Fall Backyard Burn Trail Run - Lake Fairfax

Reston, VA

Sunday, October 18th, 2026

1 Mile

10 Miles

Trail

View details for race Fall Backyard Burn Trail Run - Lake Fairfax

Fleet Feet Half Marathon

York, PA

Sunday, October 18th, 2026

Half

Trail

View details for race Fleet Feet Half Marathon

MCRRC Stone Mill 50 Mile Run

Montgomery Village, MD

Saturday, November 7th, 2026

Ultra

Trail

View details for race MCRRC Stone Mill 50 Mile Run

Schaeffer Half Marathon, 10K, 5K Trail Run

Germantown, MD

Saturday, November 7th, 2026

10K

Half

Trail

View details for race Schaeffer Half Marathon, 10K, 5K Trail Run

Fall Backyard Burn Trail Run - Riverbend

Great Falls, VA

Sunday, November 22nd, 2026

10 Miles

Trail

View details for race Fall Backyard Burn Trail Run - Riverbend

Fall Backyard Burn Trail Run - Fountainhead

Fairfax Station, VA

Sunday, December 6th, 2026

Trail

View details for race Fall Backyard Burn Trail Run - Fountainhead

Naptown Half Marathon & 10K/5K

Annapolis, MD

Saturday, December 19th, 2026

Half

10K

Trail

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

Explore more in Windsor Mill, MD

Distances:

5K 10K Half Marathon Marathon

Months:

April May June

Tags:

Trail Boston Qualifiers Fast Courses

State:

All Maryland races

Don't see your race? Add it!

Add Your Race (Free)