5K races near Annapolis, Maryland — 2026 running calendar

Oct

24

Rtb Fair Winds 5k/Fun Run

Annapolis, Maryland, United States

$15.00 - $35.00

Running

5K

Nov

26

Annapolis Turkey Trot

Annapolis, Maryland, United States

$50.00

Running

5K

Nov

29

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

Annapolis, Maryland, United States

$35.00

Running

5K 2K

Dec

05

DeCesaris Prout Cancer Foundation - Jingle Bell 5K/3K

Annapolis, Maryland, United States

$50.00

Running

5K 3K

Dec

19

Naptown Half Marathon & 10K/5K

Annapolis, Maryland, United States

$40.00 - $90.00

Running

Half-Marathon 10K 5K

Feb

13

Cupid's Chase 5K Annapolis

Annapolis, Maryland, United States

$40.00 - $10,000.00

Running

5K Platinum Sponsor Gold Sponsor Silver Sponsor +2

Mar

20

Annapolis Running Festival

Annapolis, Maryland, United States

$30.00 - $100.00

Running

Half-Marathon 10K 5K +11

Sep

18

Annapolis RUN for The Light House

Annapolis, Maryland, United States

Running Walking

Half-Marathon 5K 1.6K +1

Sep

13

9/11 Heroes Run - Annapolis

Annapolis, Maryland, United States

Running

5K 1.6K Volunteer

Sep

13

The Peake Run- Our Big Ducking 60th Anniversary Run at the Maryland Seafood Festival

Annapolis, Maryland, United States

Running

10K 5K 1.6K

Jul

11

Annapolis Striders Women's Distance Festival 5K & Run After The Women 5K

Annapolis, Maryland, United States

Running

5K

Apr

28

Annapolis Striders ET's Jesters Spring 2026 5K Beginning Runners Training

Annapolis, Maryland, United States

Running

5K