Upcoming Races Near Chestertown, MD in May, 2026

Name: Healthy Kids Running Series Spring 2026 - Glasgow/Bear, DE
Start: 2026-05-17
End: 2026-05-17
Location: Newark

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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Tacos N' Ritas Run

Newark, DE

Saturday, May 2nd, 2026

10K

View details for race Tacos N' Ritas Run

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

Running with The Devils PJ5K Run & Walk

Owings Mills, MD

Saturday, May 2nd, 2026

1 Mile

View details for race Running with The Devils PJ5K Run & Walk

Phoenix 5K

Bel Air, MD

Saturday, May 2nd, 2026

1 Mile

View details for race Phoenix 5K

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)

Spencerville Adventist Academy Cross Country 5K...

Spencerville, MD

Sunday, May 3rd, 2026

1 Mile

Fast

View details for race Spencerville Adventist Academy Cross Country 5K, 1 Mile Race, and Kids Fun Run

Run For Preservation

Monkton, MD

Sunday, May 3rd, 2026

View details for race Run For Preservation

The Shipyard 10 Miler & 5K

Pennsville, NJ

Sunday, May 3rd, 2026

10 Miles

View details for race The Shipyard 10 Miler & 5K

Brandywine Red Run

Wilmington, DE

Sunday, May 3rd, 2026

View details for race Brandywine Red Run

Strides of Strength

Stevensville, MD

Sunday, May 3rd, 2026

View details for race Strides of Strength

Ellicott City 5K/10K

Baltimore, MD

Sunday, May 3rd, 2026

10K

Fast

View details for race Ellicott City 5K/10K

The Brigade 5.7K and 1.57M Family Festival

Baltimore, MD

Sunday, May 3rd, 2026

View details for race The Brigade 5.7K and 1.57M Family Festival

Immersion Cities 5K Unity Walk/Run

Baltimore, MD

Sunday, May 3rd, 2026

View details for race Immersion Cities 5K Unity Walk/Run

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

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

Relay Elementary

Halethorpe, MD

Sunday, May 3rd, 2026

1 Mile

View details for race Relay Elementary

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

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

2026 Nurses Run

Columbia, MD

Saturday, May 9th, 2026

View details for race 2026 Nurses Run

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

Shine A Light On Stroke

Newark, DE

Saturday, May 9th, 2026

View details for race Shine A Light On Stroke

Every Hour Every Day 5K

Towson, MD

Saturday, May 9th, 2026

1 Mile

View details for race Every Hour Every Day 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

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

Miles for Moms 5K & Fun Run

Fallston, MD

Saturday, May 9th, 2026

1 Mile

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

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

Cambridge Crab Run

Cambridge, MD

Sunday, May 10th, 2026

Half

View details for race Cambridge Crab Run

I LOVE Mom 5K

Newark, DE

Sunday, May 10th, 2026

View details for race I LOVE Mom 5K

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)

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

Johnny's 5K Dash and Bash

Middle River, MD

Saturday, May 16th, 2026

View details for race Johnny's 5K Dash and Bash

Two Rivers Race Around the Lake 5K

Odenton, MD

Saturday, May 16th, 2026

View details for race Two Rivers Race Around the Lake 5K

Kennett Run

Kennett Square, PA

Saturday, May 16th, 2026

10K

1 Mile

View details for race Kennett Run

Catch Me If You Can 5K

Bel Air, MD

Saturday, May 16th, 2026

1 Mile

View details for race Catch Me If You Can 5K

Be You 5K Run/Walk

Glenn Dale, MD

Saturday, May 16th, 2026

Trail

View details for race Be You 5K Run/Walk

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

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

Braveheart 5 k

Elkton, MD

Saturday, May 16th, 2026

View details for race Braveheart 5 k

Milk Run 5K Run/Walk - Delaware Farm Bureau Fou...

Wilmington, DE

Saturday, May 16th, 2026

View details for race Milk Run 5K 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

Miles for the Mounted Patrol 5K

Wilmington, DE

Sunday, May 17th, 2026

View details for race Miles for the Mounted Patrol 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

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

Explore more in Chestertown, MD

Distances:

5K 10K Half Marathon Marathon

Months:

April May June

Tags:

Trail Boston Qualifiers Fast Courses

State:

All Maryland races

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