Not viral. Useful.

Santa Speedo Run Annapolis

Hundreds of runners strip down to Speedos and Santa hats for a one-mile jog through downtown Annapolis and City Dock to collect toys.

Holiday and seasonal · Annapolis, MD

Santa Speedo Run Annapolis is a holiday fun run in Annapolis, Maryland, whose next schedule is pending.

ProjectedCostumes encouraged

When: Next date TBA
Start ~12:30 PM (2025)
A Saturday in mid-December (Dec 13 in 2025)
Where: O'Brien's Oyster Bar & Seafood Tavern
113 Main Street
Annapolis, MD 21401 · Anne Arundel
Directions
Entry: $30 (2025)
Register
Organized by: Santa Speedo Run Annapolis / O'Brien's
Started 2006; 18th annual in 2025

What to expect

2026 Projected

Date TBA

A one-mile fun run and toy/food drive that starts and ends at O'Brien's on Main Street, followed by a party with live music.

Distances: 1-mile fun run
Occasion: Christmas
Season: Winter
Swag: Event swag
Field: More than 500 runners typically
Benefits: Boys and Girls Clubs of Annapolis and AA County; AA County Food Bank (2025)

Details checked against the race’s own pages on Sun, Oct 4, 2026.