Running Races in Annapolis, MD

INTRO 2 TRI - Your First Triathlon, Made Simple

Mar 1, 2026 Annapolis, MD

INTRO 2 TRI - Your First Triathlon, Made Simple

From $199.00 Open

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Annapolis Running Festival

Mar 21, 2026 Annapolis, MD

2025 Virtual 5KVirtual 5KVirtual 5K - Charity Registration5k - Charity Registration5K2025 Virtual 10KVirtual 10KVirtual 10K - Charity Registration10K10K - Charity RegistrationHalf Marathon - Charity RegistrationVirtual Half Marathon - Charity Registration2025 Virtual Half MarathonVirtual Half-MarathonHalf-Marathon

From $0.00 Closing Soon Open

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Escape Through The Cape

Apr 11, 2026 Annapolis, MD

1 Mile Fun Run (non-timed event)5k Run/Walk

From $30.00 Closing Soon Open

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Sandy Point State Park - Happy Little 5K

Apr 18, 2026 Annapolis, MD

5K Race Entry (NO race swag included)

From $25.00 Open

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22 Miles to Break Boundaries- 24 Hour Ultra Trail

May 16, 2026 Annapolis, MD

24 Hour Trail Run

From $150.00 Open

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Annapolis 10 Mile Run

Aug 30, 2026 Annapolis, MD

Ten Mile Run

From $100.00 Closing Soon Open

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Bay Bridge Paddle

Sep 13, 2026 Annapolis, MD

The Soft Shell Kayak DoubleSoft Shell SUP plus 1 mile beach runThe Soft Shell KayakSoft Shell Kayak plus 1 mile beach runThe Soft Shell SUPThe Steamer KayakThe Steamer Kayak DoubleThe Steamer SUPThe Span 4 person CurrachThe Span SUPThe Span Coastal Rowing SingleThe Span SurfskiThe Span Sea KayakThe Span ProneThe Span OC1The Span OC2The Span OC-6The Span 3 Person Currah

From $100.00 Open

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Annapolis RUN for The Light House

Sep 18, 2026 Annapolis, MD

1 Mile Walk (In-Person)5k (In-Person)5K (Virtual)Half Marathon (In-Person)Half Marathon (Virtual)

From $108.00 Open

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Naptown Half Marathon & 10K/5K

Dec 19, 2026 Annapolis, MD

5K10KHalf Marathon

From $40.00 Open

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