Upcoming Races Near Chestertown, MD in May, 2026

Name: Sole Circle Every Step Counts 5k and 10k
Start: 2026-05-31
End: 2026-05-31
Location: Bladensburg

Full Moon 5K Trail Run/Walk

Wilmington, DE

Friday, May 1st, 2026

Featured

View details for race Full Moon 5K Trail Run/Walk

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Luau 5K, 10K, & 13.1M at Bel Air, MD (18)

Bel Air, MD

Saturday, May 2nd, 2026

10K

Half

View details for race Luau 5K, 10K, & 13.1M at Bel Air, MD (18)

Azalea Classic

University Park, MD

Saturday, May 2nd, 2026

1 Mile

View details for race Azalea Classic

Run Fur Their Lives 5K Fun Run/Walk

Cambridge, MD

Saturday, May 2nd, 2026

View details for race Run Fur Their Lives 5K Fun Run/Walk

Go Gray in May 2026

Bladensburg, MD

Saturday, May 2nd, 2026

View details for race Go Gray in May 2026

Tacos N' Ritas Run

Newark, DE

Saturday, May 2nd, 2026

10K

View details for race Tacos N' Ritas Run

Phoenix 5K

Bel Air, MD

Saturday, May 2nd, 2026

1 Mile

View details for race Phoenix 5K

Ellicott City 5K/10K

Baltimore, MD

Sunday, May 3rd, 2026

10K

Fast

View details for race Ellicott City 5K/10K

Brandywine Red Run

Wilmington, DE

Sunday, May 3rd, 2026

View details for race Brandywine Red Run

The Shipyard 10 Miler & 5K

Pennsville, NJ

Sunday, May 3rd, 2026

10 Miles

View details for race The Shipyard 10 Miler & 5K

Shore Elite PT x Morgan's Message 5k

Stevensville, MD

Sunday, May 3rd, 2026

View details for race Shore Elite PT x Morgan's Message 5k

33rd Annual "Billy Korrow" Memorial 5K Run and ...

Towson, MD

Sunday, May 3rd, 2026

1 Mile

View details for race 33rd Annual "Billy Korrow" Memorial 5K Run and 1 Mile Fun Walk

ChristianaCare Nurses Week 5K

Newark, DE

Tuesday, May 5th, 2026

View details for race ChristianaCare Nurses Week 5K

Johnnycake Jolt Series!

Windsor Mill, MD

Wednesday, May 6th, 2026

10K

View details for race Johnnycake Jolt Series!

RSPS 11th Annual Family 5K/Fun Run

Ellicott City, MD

Friday, May 8th, 2026

1 Mile

View details for race RSPS 11th Annual Family 5K/Fun Run

Sneaks Come Out at Night 5K, presented by Brown...

Baltimore, MD

Friday, May 8th, 2026

View details for race Sneaks Come Out at Night 5K, presented by Brown Advisory

LINKing the Future 5k & 1 Mile Walk

Kennett Square, PA

Saturday, May 9th, 2026

1 Mile

View details for race LINKing the Future 5k & 1 Mile Walk

Shine A Light On Stroke

Newark, DE

Saturday, May 9th, 2026

View details for race Shine A Light On Stroke

Miles of Smiles 5K/Stroll for Joel 1M

Bel Air, MD

Saturday, May 9th, 2026

1 Mile

View details for race Miles of Smiles 5K/Stroll for Joel 1M

9th Annual Shatter the Stigma 5K

Chesapeake Beach, MD

Saturday, May 9th, 2026

1 Mile

View details for race 9th Annual Shatter the Stigma 5K

Phelps Luck 5k and Fun Run

Columbia, MD

Saturday, May 9th, 2026

1 Mile

View details for race Phelps Luck 5k and Fun Run

2026 Nurses Run

Columbia, MD

Saturday, May 9th, 2026

View details for race 2026 Nurses Run

Miles for Moms 5K & Fun Run

Fallston, MD

Saturday, May 9th, 2026

1 Mile

Trail

View details for race Miles for Moms 5K & Fun Run

Every Hour Every Day 5K

Towson, MD

Saturday, May 9th, 2026

1 Mile

View details for race Every Hour Every Day 5K

2nd Annual Eldersurg Elementary School PTA Colo...

Eldersburg, MD

Saturday, May 9th, 2026

1 Mile

View details for race 2nd Annual Eldersurg Elementary School PTA Color Run

I LOVE Mom 5K

Newark, DE

Sunday, May 10th, 2026

View details for race I LOVE Mom 5K

Cambridge Crab Run

Cambridge, MD

Sunday, May 10th, 2026

Half

View details for race Cambridge Crab Run

St. Michaels Running Festival presented by Broo...

Saint Michaels, MD

Saturday, May 16th, 2026

Half

10K

View details for race St. Michaels Running Festival presented by Brooks (CANCELED)

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

Stroll & Roll: 5K Run & Family Fun Walk to bene...

Baltimore, MD

Saturday, May 16th, 2026

1 Mile

View details for race Stroll & Roll: 5K Run & Family Fun Walk to benefit the Erin Levitas Foundation

Milk Run/Walk - Delaware Farm Bureau Foundation

Wilmington, DE

Saturday, May 16th, 2026

10K

View details for race Milk Run/Walk - Delaware Farm Bureau Foundation

Johns Hopkins Nursing 5K Fun Run & 1 Mile Fun W...

Baltimore, MD

Saturday, May 16th, 2026

1 Mile

View details for race Johns Hopkins Nursing 5K Fun Run & 1 Mile Fun Walk 2026

22 Miles to Break Boundaries- 24 Hour Ultra Trail

Annapolis, MD

Saturday, May 16th, 2026

View details for race 22 Miles to Break Boundaries- 24 Hour Ultra Trail

Keep Punching 5K, 1 Mile, and Virtual Event

Towson, MD

Saturday, May 16th, 2026

1 Mile

View details for race Keep Punching 5K, 1 Mile, and Virtual Event

Kennett Run

Kennett Square, PA

Saturday, May 16th, 2026

10K

1 Mile

View details for race Kennett Run

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

First State Trail Race

Wilmington, DE

Sunday, May 17th, 2026

10K

Ultra

Trail

View details for race First State Trail Race

Healthy Kids Running Series Spring 2026 - Glasg...

Newark, DE

Sunday, May 17th, 2026

View details for race Healthy Kids Running Series Spring 2026 - Glasgow/Bear, DE

29th Annual Race Against Domestic Violence 5K

Newark, DE

Sunday, May 17th, 2026

View details for race 29th Annual Race Against Domestic Violence 5K

Healthy Kids Running Series Spring 2026 - Middl...

Middletown, DE

Sunday, May 17th, 2026

View details for race Healthy Kids Running Series Spring 2026 - Middletown, DE

Dawn's 5k Dash

Fallston, MD

Sunday, May 17th, 2026

Trail

View details for race Dawn's 5k Dash

Miles for the Mounted Patrol 5K

Wilmington, DE

Sunday, May 17th, 2026

View details for race Miles for the Mounted Patrol 5K

17th Annual Indy 5K & Color Us Kids Run

Newark, DE

Tuesday, May 19th, 2026

1 Mile

View details for race 17th Annual Indy 5K & Color Us Kids Run

16TH WALK/JOG FOR THE "WELL" OF IT 5K

Ridgely, MD

Sunday, May 24th, 2026

View details for race 16TH WALK/JOG FOR THE "WELL" OF IT 5K

Lyme Warrior's Run Like A Warrior 5ks - Ellicot...

Ellicott, MD

Sunday, May 24th, 2026

View details for race Lyme Warrior's Run Like A Warrior 5ks - Ellicott, MD

Healthy Tilghman 5k or 1 Mile Run/Walk

Tilghman, MD

Saturday, May 30th, 2026

1 Mile

View details for race Healthy Tilghman 5k or 1 Mile Run/Walk

Conquer The Canal

Delaware City, DE

Saturday, May 30th, 2026

Marathon

10K

Trail

View details for race Conquer The Canal

Mimi's Heartbeat For Hope 5K Run/ 1 Mile Walk

Pennsville, NJ

Saturday, May 30th, 2026

1 Mile

View details for race Mimi's Heartbeat For Hope 5K Run/ 1 Mile Walk

Spring Fling 5K

Newark, DE

Saturday, May 30th, 2026

View details for race Spring Fling 5K

Sole Circle Every Step Counts 5k and 10k

Bladensburg, MD

Sunday, May 31st, 2026

10K

View details for race Sole Circle Every Step Counts 5k and 10k

Explore more in Chestertown, MD

Distances:

5K 10K Half Marathon Marathon

Months:

March April May

Tags:

Trail Boston Qualifiers Fast Courses

State:

All Maryland races

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