• Skip to main content
  • Skip to after header navigation
  • Skip to site footer
Annapolis Moms

Annapolis Moms

Making Our Community Stronger, One Connection At A Time

BUSY MOMS DON’T MISS A THING!

This field is for validation purposes and should be left unchanged.
Which emails would you like to receive?
  • Home
  • Topics
    • Arts & Entertainment
    • Community
    • Education
    • Food & Dining
    • Health & Beauty
    • Holiday
    • Home
    • Parenting
    • Retail
    • Sports
  • Events
    • All Events
    • Submit an Event
  • Thumbs Up
  • About
    • Contact
  • Coupons
  • Summer Camps
    • Summer Camp Directory
      • Account/Login
      • Manage Listings & Profile
    • Add a Summer Camp
  • Job Connect
    • View Jobs
    • Add A Job
    • My Profile
    • My Listings
    • Job Email opt-in
  • BUSY MOMS DON’T MISS A THING!

    SIGN UP FOR OUR NEWSLETTERS

    This field is for validation purposes and should be left unchanged.
    Which emails would you like to receive?
Arts & Entertainment, Christmas, Community, Holiday

Santa Speedo Run: Not Your Average Holiday Race

December 10, 2024 by Tyler Ingle

Back for its 18th year, the Santa Speedo Run is one of Annapolis’ most unique holiday traditions! Aiming to bring together the community with holiday cheer, this fundraiser for children’s toys, and food drive has impacted thousands of people in the greater Annapolis area.

On December 14 from 11:00 am to 3:00 pm, the streets of downtown Annapolis will be flooded with runners for the short race. The twist: they’ll all be in Speedos and Santa costumes! Whether you’re an avid runner or a daily walker, this run/stroll is open to all.

“[Since] 2006, we have collected and distributed thousands of toys to children in need right here in our local community,” said Kevin Chaney, event organizer. “In 2023, we expanded our outreach to include collecting food for the AA County Food Bank. The event is a fun run/stroll along Main Street, followed by a post-party at O’Brien’s.”

Photo Courtesy of Kevin Chaney/Santa Speedo Run
Photo Courtesy of BeeprBuzz
Photo Courtesy of Kevin Chaney/Santa Speedo Run

\

Registration, check-in, and donations will begin at 11:00 am, followed by a group picture and carol singing at 12:15 pm. The run/stroll will officially kick off at 12:30 pm, starting at O’Brien’s Oyster and Seafood Tavern. Following the race, there will be an after-party with the Timmie Metz Band featuring Tambo, until 3:00 pm.

Men are required to wear speedo-like bathing suits, while Santa hats and beards are strongly encouraged. For the ladies, bathing suits are preferred, but any type of skort and other Christmas gear will suffice. Thongs are not allowed, and holiday colors are a must! Wear street clothes over your race wear to stay warm before and after the race.

Anyone can make a donation, whether you are partaking in the event or not, and can do so outside of O’Brien’s at any time during the event. 

Those interested in joining the race can register here.

facebookShare on Facebook
TwitterTweet
FollowFollow us

Related posts:

Naptown Runners Go the Distance  Dickens Christmas colonialHoliday Fun that Won’t Break the Bank Bay Bridge run 1Bay Bridge Run on November 12: Unique Fun that’s Distinctly Chesapeake a lighted Rubber dinghy with snowman and santa wavingHoliday Events Happening this Week and Weekend
Category: Arts & Entertainment, Christmas, Community, HolidayTag: Activities, Annapolis See all posts by Tyler Ingle

About Tyler Ingle

Previous Post:SPCA’s Adoptable Pet: This Week’s Heartthrob
Next Post:Winter Break Guide 2024winter break guide cover

Sidebar

Categories

• Arts & Entertainment
• Community
• Do Not Miss
• Education
• Food & Dining
• Health & Beauty
• Holiday
• Home
• Parenting
• Retail
• Sports
• Updates

Comments Box SVG iconsUsed for the like, share, comment, and reaction icons

The Latest from our Facebook Page

Play

🚗✨ Road Trip Ready with Annapolis Moms is here!

First stop: St. Michaels! 🌊⚓️

Looking for the perfect summer day trip? We’ve mapped out everything you need, from where to grab your morning coffee and the can’t-miss stops at the Chesapeake Bay Maritime Museum to waterfront dining, boutique shopping, sweet treats, and even sunset sails.

Whether you’re planning a family adventure, a girls’ day, or a date on the Eastern Shore, St. Michaels is the kind of place you’ll want to visit again and again.

Ready to hit the road? The full day-trip guide is linked in our bio! Save this post for your next weekend adventure, and tell us where we should go next for Road Trip Ready with Annapolis Moms! 🚙☀️

#AnnapolisMoms #RoadTripReady #StMichaelsMD #EasternShoreMD #DayTrip
... See MoreSee Less

1 day ago
View Comments likes Like love 3 Comments: 0 Shares: 1
Share
Share on Facebook Share on Twitter Share on LinkedIn Share by Email

0 CommentsComment on Facebook

Summer brings a chan

Summer brings a change of pace. ☀️

Travel plans, busy schedules, and time away can make it harder to stay closely connected to aging loved ones.

Having trusted support at home ensures continuity of care, so you can enjoy time away knowing someone is there when it matters most.

Angel Care Network | Home Care MD has been a trusted resource for local families for over 20 years. As a woman-owned Annapolis-area business and proud Annapolis Moms community sponsor, they help match families with caregivers who provide dependable support and meaningful companionship.

Learn more at www.angelcarenetwork.com
... See MoreSee Less

2 days ago
View Comments likes Like 0 Comments: 0 Shares: 0
Share
Share on Facebook Share on Twitter Share on LinkedIn Share by Email

0 CommentsComment on Facebook

JOIN THE COMMUNITY

  • Facebook
  • Instagram
  • TikTok
  • YouTube

HELPFUL LINKS

  • Community Sponsorship
  • Privacy Policy
  • Terms of Service
  • Disclaimer
  • EULA
  • Thumbs Up & Plaques

BUSY MOMS DON’T MISS A THING!

This field is for validation purposes and should be left unchanged.
Which emails would you like to receive?

Copyright © 2026 · Annapolis Moms · All Rights Reserved · Powered by AE2 Creative

Change Location
Find awesome listings near you!