Upcoming 5K Races Near Trappe, MD

Name: Annapolis Running Festival
Start: 2026-03-21
End: 2026-03-21
Location: Annapolis

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3rd Annual Build-a-Gym 5K

Federalsburg, MD

Saturday, September 6th, 2025

View details for race 3rd Annual Build-a-Gym 5K

Skipjack Run

Deal Island, MD

Saturday, September 6th, 2025

10K

View details for race Skipjack Run

21ST CANNONBALL 5k Race & Trenny Elliott Memori...

Lewes, DE

Sunday, September 7th, 2025

1 Mile

View details for race 21ST CANNONBALL 5k Race & Trenny Elliott Memorial Walk

Kent Goes Purple 5K Color Fun Run/Walk

Chestertown, MD

Sunday, September 7th, 2025

View details for race Kent Goes Purple 5K Color Fun Run/Walk

Annapolis RUN for The Light House

Annapolis, MD

Friday, September 12th, 2025

Half

1 Mile

View details for race Annapolis RUN for The Light House

Journey to ExSCellence 5K Walk/Run 2025

Capitol Heights, MD

Saturday, September 13th, 2025

View details for race Journey to ExSCellence 5K Walk/Run 2025

Journey to ExSCellence 5K Walk/Run 2025

District Heights, MD

Saturday, September 13th, 2025

View details for race Journey to ExSCellence 5K Walk/Run 2025

Bay Bridge Paddle

Annapolis, MD

Sunday, September 14th, 2025

1 Mile

View details for race Bay Bridge Paddle

Stef Ripple 9th Annual Stefanie Ashdown Memoria...

Arnold, MD

Sunday, September 14th, 2025

1 Mile

View details for race Stef Ripple 9th Annual Stefanie Ashdown Memorial Do Your Best 5k Run and 1 Mile Walk

9/11 Heroes Run - Annapolis

Annapolis, MD

Sunday, September 14th, 2025

1 Mile

View details for race 9/11 Heroes Run - Annapolis

My Sole Knows 5K Virtual Run/Walk/Virtual

District Heights, MD

Saturday, September 20th, 2025

View details for race My Sole Knows 5K Virtual Run/Walk/Virtual

Munro Hampton Alumni Association DC 5K Run-Walk

Upper Marlboro, MD

Saturday, September 20th, 2025

View details for race Munro Hampton Alumni Association DC 5K Run-Walk

St. Charles Running Festival

Waldorf, MD

Saturday, September 20th, 2025

10K

View details for race St. Charles Running Festival

10TH PARADISE GRILL "Stop-Drop & Run" 5k Run & ...

Long Neck, DE

Sunday, September 21st, 2025

Trail

Fast

View details for race 10TH PARADISE GRILL "Stop-Drop & Run" 5k Run & Walk

The Kellie Thompson Shiley 5k and Family Fun Run

Stevensville, MD

Sunday, September 21st, 2025

1 Mile

Trail

View details for race The Kellie Thompson Shiley 5k and Family Fun Run

The Samuel Lomax Foundation, Inc. and Cedar - ...

Glen Burnie, MD

Sunday, September 21st, 2025

View details for race The Samuel Lomax Foundation, Inc. and Cedar - Morris Hill 4th Annual Cancer Awareness 5K Run/Walk

Claude Hall 5K Funday Fundraiser

Snow Hill, MD

Saturday, September 27th, 2025

1 Mile

View details for race Claude Hall 5K Funday Fundraiser

The Ivy Community Charities of Prince George's ...

Upper Marlboro, MD

Saturday, September 27th, 2025

Ultra

View details for race The Ivy Community Charities of Prince George's County, Inc. -30th Annual 5K Walk-Run Soul Fitness Weekend

Friends of the Poor 5K Walk/Run & Kiddy-K

Owings, MD

Saturday, October 4th, 2025

Trail

Fast

View details for race Friends of the Poor 5K Walk/Run & Kiddy-K

Freedom From Seizures 5K South

Dover, DE

Saturday, October 11th, 2025

View details for race Freedom From Seizures 5K South

9th Ashley Furio 5K Run/Walk

Lewes, DE

Saturday, October 11th, 2025

Fast

View details for race 9th Ashley Furio 5K Run/Walk

Pirate's Wharf 5K

Quantico, MD

Saturday, October 11th, 2025

View details for race Pirate's Wharf 5K

Run the Vineyards - Running Hare Fall 5K

Prince Frederick, MD

Sunday, October 12th, 2025

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

Chestertown Challenge Half Marathon Run and 5K ...

Chestertown, MD

Sunday, October 12th, 2025

Half

View details for race Chestertown Challenge Half Marathon Run and 5K Run/Walk

Tides of Grace 5K

Stevensville, MD

Saturday, October 18th, 2025

View details for race Tides of Grace 5K

Calvert Health Foundation Breast Cancer 5K Run/...

Solomons, MD

Saturday, October 18th, 2025

1 Mile

View details for race Calvert Health Foundation Breast Cancer 5K Run/Walk

5th Annual Lace Up for Ag Literacy 5K Run/Walk ...

Lewes, DE

Saturday, October 18th, 2025

View details for race 5th Annual Lace Up for Ag Literacy 5K Run/Walk - Delaware Farm Bureau Foundation

First Coast Realty 5K

Dover, DE

Saturday, October 18th, 2025

1 Mile

View details for race First Coast Realty 5K

12th Annual St. John's School Eagle 5K

Hollywood, MD

Saturday, October 18th, 2025

1 Mile

View details for race 12th Annual St. John's School Eagle 5K

OCC 5k for Mental Health

Oxford, MD

Saturday, October 18th, 2025

1 Mile

10K

View details for race OCC 5k for Mental Health

PRO-Vision Memorial Run

Severna Park, MD

Saturday, October 18th, 2025

10K

View details for race PRO-Vision Memorial Run

RTB Fair Winds 5k/Fun Run

Annapolis, MD

Saturday, October 25th, 2025

Trail

View details for race RTB Fair Winds 5k/Fun Run

North Point Fright Night 5K & Haunted Trail

Waldorf, MD

Saturday, October 25th, 2025

Trail

View details for race North Point Fright Night 5K & Haunted Trail

Be Great 5K

Dover, DE

Sunday, October 26th, 2025

View details for race Be Great 5K

The Captain James Lovell Space Walk & Run 5K

Saint Marys City, MD

Sunday, November 2nd, 2025

View details for race The Captain James Lovell Space Walk & Run 5K

Historic Drawbridge Running Festival

St Michaels, MD

Saturday, November 8th, 2025

Half

Marathon

Fast

View details for race Historic Drawbridge Running Festival

Harvest Hustle 5K

Camden Wyoming, DE

Saturday, November 8th, 2025

View details for race Harvest Hustle 5K

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

Lewes, DE

Saturday, November 15th, 2025

Fast

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

North Shore 5th Annual Turkey Trot

Pasadena, MD

Thursday, November 27th, 2025

View details for race North Shore 5th Annual Turkey Trot

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

View details for race Turkey Trot 5K

Rail Haus Turkey Burn 5K

Dover, DE

Saturday, November 29th, 2025

View details for race Rail Haus Turkey Burn 5K

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

Run Like The Dickens 5K Run/Walk

Chestertown, MD

Saturday, December 6th, 2025

View details for race Run Like The Dickens 5K 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

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

View details for race Hot Chocolate 5K

Inaugural Sandhill Summer Countdown 5k Run/Walk

Georgetown, DE

Saturday, February 21st, 2026

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

The Holly’s Hustle 5k Run/Walk

Smyrna, DE

Sunday, March 8th, 2026

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

Annapolis Running Festival

Annapolis, MD

Saturday, March 21st, 2026

Half

10K

View details for race Annapolis Running Festival

Explore more in Trappe, MD

Distances:

5K 10K Half Marathon Marathon

Months:

September October November

Tags:

Trail Boston Qualifiers Fast Courses

State:

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