Runners and walking families enjoying a morning trot across an open scenic bridge
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Fleet Feet Annapolis Turkey Trot 5K (City Dock & Historic Downtown)

Thu, Nov 269:00 AM – 11:00 AM · Thanksgiving Day, Thursday, November 26, 2026; 8:30 AM costume contest lineup; 9:00 AM fun run step-off; finishes at City Dock / Eastport by 11:00 AM

Fleet Feet Annapolis (Eastport to City Dock)318 6th St, Annapolis, MD 21403 · 22.9 mi approx. from BaltimoreDirections

All ages welcome; stroller-friendly course; costume prizes for best turkey and holiday outfits; dogs welcome with treats

From $20$20 youth & adult fun run entry; 100% of proceeds benefit Girls on the Run Greater Chesapeake; advance online registration required (no race-day signups)

About this adventure

Celebrating its 20th annual running on Thanksgiving morning, the Fleet Feet Annapolis Turkey Trot 5K is one of Maryland’s most scenic and festive holiday traditions. Beginning in charming Eastport at Fleet Feet’s historic location, the untimed fun run crosses the iconic Eastport Bridge and sweeps into historic Downtown Annapolis, taking participants along waterfront City Dock, Randall Street, and past the Maryland State House before returning across the harbor. Family Experience & Accessibility: • Stroller Accessibility: Paved downtown sidewalks and asphalt roadways; wide sidewalks along Eastport Bridge and City Dock provide smooth stroller rolling. • Nursing & Rest Spots: City Dock public restrooms and benches overlooking the harbor offer resting spots before and after the trot. • Age Suitability: Completely family-focused; untimed format encourages casual walking with strollers, kids, and costumed family members. • Sensory Tips: Annapolis streets remain open to regular morning foot and vehicle traffic, with friendly volunteer marshals at crossings; bells and turkey gobble calls create a lighthearted, cheerful buzz.

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