Upcoming 5K Races Near Trappe, MD

Name: Skipjack Run
Start: 2026-09-12
End: 2026-09-12
Location: Deal Island

Historic Drawbridge Running Festival

St Michaels, MD

Saturday, November 8th, 2025

Featured

Half

Marathon

View details for race Historic Drawbridge Running Festival

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Harvest Hustle 5K

Camden Wyoming, DE

Saturday, November 8th, 2025

View details for race Harvest Hustle 5K

3RD NICOLA PIZZA RUN/WALK

Lewes, DE

Saturday, November 8th, 2025

View details for race 3RD NICOLA PIZZA RUN/WALK

Tunnel to Towers 5K Run & Walk - Delaware Beach...

Lewes, DE

Saturday, November 15th, 2025

View details for race Tunnel to Towers 5K Run & Walk - Delaware Beaches, DE

INAUGURAL ROYAL PORT PASSAGE 5K RUN/WALK...Snow...

Snowhill, MD

Sunday, November 16th, 2025

Fast

View details for race INAUGURAL ROYAL PORT PASSAGE 5K RUN/WALK...Snowhill, MD

North Shore 5th Annual Turkey Trot

Pasadena, MD

Thursday, November 27th, 2025

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Annapolis Turkey Trot

Annapolis, MD

Thursday, November 27th, 2025

View details for race Annapolis Turkey Trot

Gobble Gallop 5K

Lexington Park, MD

Thursday, November 27th, 2025

View details for race Gobble Gallop 5K

2ND IRISH EYES FRIENDSGIVING 5K RUN/WALK in hon...

Lewes, DE

Thursday, November 27th, 2025

Fast

View details for race 2ND IRISH EYES FRIENDSGIVING 5K RUN/WALK in honor of longtime bartender Don Johnson

Turkey Trot 5K

Saint Leonard, MD

Thursday, November 27th, 2025

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Rail Haus Turkey Burn 5K

Dover, DE

Saturday, November 29th, 2025

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Santa Fun Run 5k for Hospice

Easton, MD

Saturday, November 29th, 2025

View details for race Santa Fun Run 5k for Hospice

St. Mary's Boys Basketball Annual 5K Run and 1-...

Annapolis, MD

Sunday, November 30th, 2025

View details for race St. Mary's Boys Basketball Annual 5K Run and 1-Mile Fun Run

Boundless Edventures 5K Family Run/Walk

Millersville, MD

Sunday, November 30th, 2025

View details for race Boundless Edventures 5K Family Run/Walk

2025 Jingle Bell Run - Solomon's Island, MD

Solomon's Island, MD

Saturday, December 6th, 2025

View details for race 2025 Jingle Bell Run - Solomon's Island, MD

DeCesaris Prout Cancer Foundation - Jingle Bell...

Annapolis, MD

Saturday, December 6th, 2025

View details for race DeCesaris Prout Cancer Foundation - Jingle Bell 5K/3K

First Coast Realty 5K

Dover, DE

Saturday, December 6th, 2025

1 Mile

View details for race First Coast Realty 5K

Run Like The Dickens 5K Run/Walk

Chestertown, MD

Saturday, December 6th, 2025

View details for race Run Like The Dickens 5K Run/Walk

Naptown Half Marathon & 10K/5K

Annapolis, MD

Saturday, December 20th, 2025

Half

10K

Trail

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

Hot for Chocolate 5K

Saint Leonard, MD

Saturday, February 14th, 2026

View details for race Hot for Chocolate 5K

Hot Chocolate 5K

Stevensville, MD

Sunday, February 15th, 2026

Trail

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Inaugural Sandhill Summer Countdown 5k Run/Walk

Georgetown, DE

Saturday, February 21st, 2026

View details for race Inaugural Sandhill Summer Countdown 5k Run/Walk

21st Tim Kennard River Run- 10 miler & 5k Run

Salisbury, MD

Sunday, March 1st, 2026

10 Miles

View details for race 21st Tim Kennard River Run- 10 miler & 5k Run

The Holly’s Hustle 5k Run/Walk

Smyrna, DE

Sunday, March 8th, 2026

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

13th annual Lucky Leprechaun 5k

Milton, DE

Sunday, March 8th, 2026

View details for race 13th annual Lucky 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

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

RunSBY Events (Salisbury Marathon/Salisbury Hal...

Salisbury, MD

Saturday, April 4th, 2026

Marathon

Half

Fast

View details for race RunSBY Events (Salisbury Marathon/Salisbury Half Marathon/5k)

STEVE 5K

White Plains, MD

Saturday, April 25th, 2026

Trail

View details for race STEVE 5K

2025 Country School Black & Gold Run and Fun Fest

Easton, MD

Sunday, April 26th, 2026

1 Mile

View details for race 2025 Country School Black & Gold Run and Fun Fest

Run For The Kids 5K

Saint Marys City, MD

Saturday, May 2nd, 2026

View details for race Run For The Kids 5K

Run the Vineyards - Running Hare 5K

Prince Frederick, MD

Saturday, May 2nd, 2026

View details for race Run the Vineyards - Running Hare 5K

Race4Warriors 5K, 10K & Half Marathon Challenges!

Lewes, DE

Saturday, May 9th, 2026

10K

Half

View details for race Race4Warriors 5K, 10K & Half Marathon Challenges!

Healthy Tilghman 5k or 1 Mile Run/Walk

Tilghman, MD

Saturday, June 6th, 2026

1 Mile

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

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

Run to the Taproom - Mully's Brewery Father's D...

Prince Frederick, MD

Sunday, June 21st, 2026

1 Mile

View details for race Run to the Taproom - Mully's Brewery Father's Day 5K

Blacklight Run | Maryland 2026

Mechanicsville, MD

Saturday, July 11th, 2026

Fast

View details for race Blacklight Run | Maryland 2026

Muddy Dash | Maryland

Mechanicsville, MD

Saturday, August 29th, 2026

View details for race Muddy Dash | Maryland

Skipjack Run

Deal Island, MD

Saturday, September 12th, 2026

10K

View details for race Skipjack Run

Explore more in Trappe, MD

Distances:

5K 10K Half Marathon Marathon

Months:

November December January

Tags:

Trail Boston Qualifiers Fast Courses

State:

All Maryland races

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