Running Races in Annapolis, Maryland 2026 | Browse All Races

22 Miles to Break Boundaries- 24 Hour Ultra Trail

Sat, May 16 · Annapolis, MD Annapolis

Ultra 24 Hour Trail Run

From $150 Open

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Junior Striders by Annapolis Striders

Mon, May 18 · Annapolis, MD Annapolis

Open

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"Copper the Bloodhound's K9 Mile RUCK/Walk" Benefitting Chesapeake K9 Fund

Sat, Jun 6 · Annapolis, MD Annapolis

Copper the Bloodhound's K9 Mile Ruck

From $30 Open

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Annapolis Striders John Wall Memorial One Mile Track Run

Sat, Jun 27 · Annapolis, MD Annapolis

Road Annapolis Striders John Wall Memorial One Mile Track Run

From $15 Open

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

Sat, Jul 11 · Annapolis, MD Annapolis

Road Run After The Women 5KWomen's Distance Festival 5K

From $22.5 Closed

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Annapolis 10 Mile Run

Sun, Aug 30 · Annapolis, MD Annapolis

Road Ten Mile Run

From $65 Open Closing Soon

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Bay Bridge Paddle

Sun, Sep 13 · Annapolis, MD Annapolis

Triathlon Soft Shell SUP plus 1 mile beach runThe Soft Shell KayakSoft Shell Kayak plus 1 mile beach run +15

From $50 Open Closing Soon

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Annapolis RUN for The Light House

Fri, Sep 18 · Annapolis, MD Annapolis

Virtual 1 Mile Walk (In-Person)5k (In-Person)5K (Virtual) +2

From $25 Open 32 spots left

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Bay Bridge Walk/Run for a Cause - Walk the Walk Foundation

Sun, Nov 8 · Annapolis, MD Annapolis

Road 10K - Walk the Walk Participant

From $70 Open Closing Soon

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Bay Bridge Run

Sun, Nov 8 · Annapolis, MD Annapolis

Virtual 2025 10K Virtual Run*10KVirtual 10K +10

From $0 Closed

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Naptown Half Marathon & 10K/5K

Sat, Dec 19 · Annapolis, MD Annapolis

Road 5K10KHalf Marathon

From $40 Open

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Running Races in Annapolis, Maryland — 2026

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