Upcoming 5K Races Near Chestertown, MD

Name: Go Gray in May 2026
Start: 2026-05-02
End: 2026-05-02
Location: Bladensburg

Naptown Half Marathon & 10K/5K

Annapolis, MD

Saturday, December 20th, 2025

Featured

Half

10K

Trail

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

Want to feature your race?

Get your race seen first by thousands of runners

Learn More

Learn how to feature your race

Reindeer Run 5k

Aberdeen, MD

Saturday, December 20th, 2025

1 Mile

Fast

View details for race Reindeer Run 5k

Autumn Arch Winter Warmer 5K

Newark, DE

Sunday, December 28th, 2025

Fast

View details for race Autumn Arch Winter Warmer 5K

Resolution Run 2026

Baltimore, MD

Thursday, January 1st, 2026

1 Mile

15K

View details for race Resolution Run 2026

Resolution Run 5K

Perryville, MD

Thursday, January 1st, 2026

1 Mile

View details for race Resolution Run 5K

Hoppy New Year 5K

Newark, DE

Thursday, January 1st, 2026

View details for race Hoppy New Year 5K

New Year 5K, 10K, & 13.1M, Bel Air, MD (01)

Bel Air, MD

Saturday, January 3rd, 2026

10K

Half

View details for race New Year 5K, 10K, & 13.1M, Bel Air, MD (01)

Tyler Brown's "I Hate to Run" Memorial 5K

Wilmington, DE

Sunday, January 11th, 2026

View details for race Tyler Brown's "I Hate to Run" Memorial 5K

Cocoa & Cupcakes 5K

Newark, DE

Saturday, January 24th, 2026

View details for race Cocoa & Cupcakes 5K

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

Viking 5K, 10K & Half Marathon at Cedar Lane Re...

Bel Air, MD

Saturday, February 7th, 2026

10K

Half

View details for race Viking 5K, 10K & Half Marathon at Cedar Lane Regional Park, Bel Air, MD (06M80)

Touchdown 5K

Newark, DE

Sunday, February 8th, 2026

View details for race Touchdown 5K

Cupid's Chase 5K Baltimore

Baltimore, MD

Saturday, February 14th, 2026

View details for race Cupid's Chase 5K Baltimore

Valentine's Day 5K

Millersville, MD

Saturday, February 14th, 2026

View details for race Valentine's Day 5K

Hot Chocolate 5K

Stevensville, MD

Sunday, February 15th, 2026

Trail

View details for race Hot Chocolate 5K

atTAcK addiction 5K

New Castle, DE

Saturday, March 7th, 2026

View details for race atTAcK addiction 5K

Medal Madness 5K, 10K & Half Marathon at Cedar ...

Bel Air, MD

Saturday, March 7th, 2026

10K

Half

View details for race Medal Madness 5K, 10K & Half Marathon at Cedar Lane Regional Park, Bel Air, MD (10M80)

The Holly’s Hustle 5k Run/Walk

Smyrna, DE

Sunday, March 8th, 2026

View details for race The Holly’s Hustle 5k Run/Walk

Catch the Leprechaun 5K

Newark, DE

Saturday, March 14th, 2026

View details for race Catch the Leprechaun 5K

18th Annual St. Patrick's Day 5k, 1m Fun Run, 2...

Denton, MD

Saturday, March 14th, 2026

1 Mile

Fast

View details for race 18th Annual St. Patrick's Day 5k, 1m Fun Run, 200m Kiddie Dash

Altra Kelly Benefits St. Patrick's Day Shamrock 5K

Baltimore, MD

Sunday, March 15th, 2026

View details for race Altra Kelly Benefits St. Patrick's Day Shamrock 5K

St. Patrick's Revenge 5K

Wilmington, DE

Sunday, March 15th, 2026

View details for race St. Patrick's Revenge 5K

2026 Barlowe Bolt

Millersville, MD

Saturday, March 21st, 2026

1 Mile

View details for race 2026 Barlowe Bolt

Annapolis Running Festival

Annapolis, MD

Saturday, March 21st, 2026

Half

10K

View details for race Annapolis Running Festival

Spring in the Meadow 5K

Winterthur, DE

Friday, March 27th, 2026

View details for race Spring in the Meadow 5K

Kenya Connect 5K: Running/Walking for Education

Ellicott City, MD

Saturday, March 28th, 2026

View details for race Kenya Connect 5K: Running/Walking for Education

Tiger Trot 5K

Rising Sun, MD

Saturday, March 28th, 2026

View details for race Tiger Trot 5K

Colorectal Cancer Awareness 5K Walk-Run

Fallston, MD

Saturday, March 28th, 2026

View details for race Colorectal Cancer Awareness 5K Walk-Run

2026 Annual Memory Walk/Recovery Run by Rage Ag...

Bel Air, MD

Wednesday, April 1st, 2026

1 Mile

View details for race 2026 Annual Memory Walk/Recovery Run by Rage Against Addiction

Donate Life Family Fun Run

Baltimore, MD

Saturday, April 4th, 2026

View details for race Donate Life Family Fun Run

Pirate 5K, 10K & Half Marathon at Cedar Lane Re...

Bel Air, MD

Saturday, April 4th, 2026

10K

Half

View details for race Pirate 5K, 10K & Half Marathon at Cedar Lane Regional Park, Bel Air, MD (14M80)

Chocolate Bunny 5K

Newark, DE

Saturday, April 4th, 2026

View details for race Chocolate Bunny 5K

Bunny Run 5K

Aberdeen, MD

Saturday, April 4th, 2026

1 Mile

View details for race Bunny Run 5K

Mt. Salem in Rockford Park - Jesus 5K

Wilmington, DE

Saturday, April 4th, 2026

View details for race Mt. Salem in Rockford Park - Jesus 5K

Turtle Derby 5k Trail Race

Havre De Grace, MD

Saturday, April 11th, 2026

View details for race Turtle Derby 5k Trail Race

Races for the Oasis 5K & Fun Run

Baltimore, MD

Saturday, April 11th, 2026

1 Mile

View details for race Races for the Oasis 5K & Fun Run

Aberdeen Proving Ground Run To Honor 5K Run/Walk

Aberdeen Proving Ground, MD

Saturday, April 11th, 2026

View details for race Aberdeen Proving Ground Run To Honor 5K Run/Walk

Coffee Run (5K)

Newark, DE

Sunday, April 12th, 2026

View details for race Coffee Run (5K)

Mimosas for Marrow 5K

Wilmington, DE

Saturday, April 18th, 2026

View details for race Mimosas for Marrow 5K

Cumberland County Historical Running Festival a...

Greenwich, NJ

Saturday, April 18th, 2026

10K

1 Mile

Fast

View details for race Cumberland County Historical Running Festival at Greenwich

Discover Downtown Columbia 5K/10K

Columbia, MD

Sunday, April 19th, 2026

10K

View details for race Discover Downtown Columbia 5K/10K

Delaware Running Festival

Wilmington, DE

Sunday, April 19th, 2026

Marathon

Half

10K

View details for race Delaware Running Festival

15th Annual Red Shoe Shuffle 5k Run & Walk

Baltimore, MD

Sunday, April 19th, 2026

View details for race 15th Annual Red Shoe Shuffle 5k Run & Walk

HealthCare Access Maryland’s 5K For the Health ...

Baltimore, MD

Saturday, April 25th, 2026

1 Mile

View details for race HealthCare Access Maryland’s 5K For the Health of It!

Nick Mowers Memorial 5K Run/Walk

Pennsville, NJ

Saturday, April 25th, 2026

View details for race Nick Mowers Memorial 5K Run/Walk

Hagley 5K/1K Along the Brandywine

Wilmington, DE

Saturday, April 25th, 2026

View details for race Hagley 5K/1K Along the Brandywine

Country School Black & Gold Run and Fun Fest

Easton, MD

Sunday, April 26th, 2026

1 Mile

View details for race Country School Black & Gold Run and Fun Fest

Tunnel to Towers Climb - Towson, MD

Towson, MD

Sunday, April 26th, 2026

View details for race Tunnel to Towers Climb - Towson, MD

Trolley Retro Run 5K

Wilmington, DE

Sunday, April 26th, 2026

View details for race Trolley Retro Run 5K

Go Gray in May 2026

Bladensburg, MD

Saturday, May 2nd, 2026

View details for race Go Gray in May 2026

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

Don't see your race? Add it!

Add Your Race (Free)