# Running Races in Annapolis, MD (2026)

> 10 upcoming races in and around Annapolis, Maryland.

- **Page:** https://runthis.run/races/maryland/annapolis

## Races

- **[RTB Fair Winds 5k/Fun Run](https://runthis.run/event/rs-151460-rtb-fair-winds-5k-fun-run)** — Sat, Oct 24, 2026 · 12:00 AM UTC · Annapolis, MD · 5K
- **[Bay Bridge Run](https://runthis.run/event/rs-113571-bay-bridge-run)** — Sun, Nov 8, 2026 · 12:00 AM UTC · Annapolis, MD · 10K
- **[Bay Bridge Walk/Run for a Cause - Walk the Walk Foundation](https://runthis.run/event/rs-146884-bay-bridge-walk-run-for-a-cause-walk-the-walk-foundation)** — Sun, Nov 8, 2026 · 12:00 AM UTC · Annapolis, MD · 10K
- **[Annapolis Turkey Trot](https://runthis.run/event/rs-120304-annapolis-turkey-trot)** — Thu, Nov 26, 2026 · 12:00 AM UTC · Annapolis, MD · 5K
- **[St. Mary's Boys Basketball Annual 5K Run and 1-Mile Fun Run](https://runthis.run/event/rs-150123-st-marys-boys-basketball-annual-5k-run-and-1-mile-fun-run)** — Sun, Nov 29, 2026 · 12:00 AM UTC · Annapolis, MD · 5K / 1.2 mi
- **[DeCesaris Prout Cancer Foundation - Jingle Bell 5K/3K](https://runthis.run/event/rs-193263-decesaris-prout-cancer-foundation-jingle-bell-5k-3k)** — Sat, Dec 5, 2026 · 12:00 AM UTC · Annapolis, MD · 5K / 1.9 mi
- **[Anniversary Run 15K](https://runthis.run/event/rs-117928-anniversary-run-15k)** — Sun, Dec 13, 2026 · 12:00 AM UTC · Annapolis, MD · 9.3 mi
- **[Naptown Half Marathon & 10K/5K](https://runthis.run/event/rs-81335-naptown-half-marathon-10k-5k)** — Sat, Dec 19, 2026 · 12:00 AM UTC · Annapolis, MD · Marathon / 10K / 5K
- **[Cupid's Chase 5K Annapolis](https://runthis.run/event/rs-213459-cupids-chase-5k-annapolis)** — Sat, Feb 13, 2027 · 12:00 AM UTC · Annapolis, MD · 5K
- **[Annapolis Running Festival](https://runthis.run/event/rs-140580-annapolis-running-festival)** — Sat, Mar 20, 2027 · 12:00 AM UTC · Annapolis, MD · Marathon / 10K / 5K

## Races by distance in Annapolis

- [5K races in Annapolis (7)](https://runthis.run/races/maryland/annapolis/5k.md)
- [10K races in Annapolis (4)](https://runthis.run/races/maryland/annapolis/10k.md)

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Source: [https://runthis.run/races/maryland/annapolis](https://runthis.run/races/maryland/annapolis) — data from Run This (runthis.run).