The Bravest (and Coldest) Tradition in Annapolis
Downtown Annapolis turns into a funny winter show every December when hundreds of runners run through the streets wearing only Speedos and Santa hats. In 2025, on December 13, the Santa Speedo Run Annapolis will be a one-mile charity jog that will raise money for local charities like the Boys & Girls Clubs and the AA County Food Bank.
The spirit, not speed, is what matters. Be ready for holiday chaos, cheeky outfits, and lots of chances to take pictures. This is one of the most famous and photographed events in the city. It combines a sense of adventure with holiday cheer.
Let’s explore more about things to do in Annapolis’s Santa Speedo Run 2025 event with Zavros Place.
Event Details: The Who, When, and Where (2025)
The Santa Speedo Run Annapolis 2025 is on Saturday, December 13, 2025. Mark your calendars. Every year, this event brings together both locals and tourists for a day of holiday fun, crazy outfits, and giving to charity.
Where Should I Go? At 113 Main Street in downtown Annapolis, O’Brien’s Oyster Bar & Seafood Tavern is where the event starts and finishes. O’Brien’s is where people meet for registration, the fun activities before the run, and the lively party afterward. It is known as the event’s “Base Camp.”
So that the fun and energy stay high, the plan is as follows:
- 11:00 AM: Check-in and Donations: People come in, drop off toys and books for kids in the area, and have a drink from the bar.
- 12:15 PM: Carols and Photos: Everyone meets outside to sing holiday songs and take pictures as a group, which sets the mood for the run.
- The Run Starts at 12:30 PM: You can jog or walk the mile path, which goes through downtown Annapolis and City Dock. It is short and sweet, and the whole point is to spread happiness.
- 12:30 PM to 3:00 PM: After-Party: The party goes on at O’Brien’s with drinks, live music from the Timmie Metz Band, and lots of laughs.
The course is only one mile on purpose to keep the fun and not the race in mind. A lot of people come out in Speedos, Santa hats, and clever holiday costumes to brave the cold. This makes it one of the most photographed events in Annapolis every year.
Besides being a show, the Santa Speedo Run is about helping people. The event in 2025 will raise money for the AA County Food Bank and the Boys & Girls Clubs of Annapolis and Anne Arundel County. It will focus on collecting toys and books for kids ages 6 to 12. This custom is a mix of humor, kindness, and community spirit.
Participation Guide: Do I Have to Wear a Speedo?
The Dress Code
Do you have to wear a Speedo? That is the big question. Not at all. While Speedos are kind of like an unofficial uniform and are a big part of the show, the outfits are what really make the event special. There will be clothes for Santa and elves, as well as holiday-themed underwear, bikinis, and even reindeer ears. The only rule? Have a happy and fun time. You will fit in whether you go for a bold or cozy look.
The “Run”
You can walk or jog a mile through downtown Annapolis and City Dock. This is not a race. There is no time limit, no stress, and no need to be active. Everyone can use the short, easy-to-find route, from experienced runners to people who just like to walk. Not breaking records is the point; it is to spread joy.
Registration
It is easy to sign up, and the group is the focus. You do not have to sign up or pay to enter online; just go to O’Brien’s Oyster Bar & Seafood Tavern on the day of the event.
Bring a new, unwrapped book or toy for kids ages 6 to 12, or cash or a check to help the Boys & Girls Clubs and the AA County Food Bank. From 11 AM to 12:15 PM, you can Register Now, drop off donations, and meet other people before the run.
Everyone Is Welcome
This event promotes body acceptance and welcomes everyone. An amazing number of people will be cheering you on, whether you are wearing a Speedo, a Santa robe, or something else. The vibe is friendly, funny, and brave without shame. Feel joy, not judge.
Spectator Tips: Best Places to Watch
The Speedo Run in Santa Annapolis is not just for people who are competing; every year, hundreds of people come to see the show.
The crazy clothes and happy holiday spirit make it a feel-good event that is fun to watch as well as take part in. You will be a part of one of Annapolis’s most photographed and talked-about events, whether you are there to cheer on friends or just take it all in.
Main Street
O’Brien’s Oyster Bar & Seafood Tavern on 113 Main Street is where the run starts and finishes, so this is the best place to see it. Runners come here to sign up, sing carols, and take group pictures before going down Main Street in a wave of red Speedos, Santa suits, and other costumes with holiday themes. Start getting there early and find a spot on the sidewalk near O’Brien’s if you want to see the whole game.
City Dock (Ego Alley)
Running groups make a loop through downtown and go by City Dock, which is also known as “ego alley” in the area. This place by the water has wide, clear views and lots of room to watch the people go by. Families, artists, and anyone else who wants to run with a beautiful view will love this place. This area sets the party mood, with music, cheering, and lots of photo-worthy moments.
Photography: Don’t Forget Your Camera
This event is perfect for Instagram. There are a lot of memorable shots, from the outfits to how the crowd reacts. You should be ready to take pictures of random moments, group poses, and the happy chaos of the run, whether you have a DSLR or just your phone. A lot of people come to the event just to take pictures, so do not be shy, snap away, and share the joy.
The after-party: Warming up at O’Brien’s
At O’Brien’s Oyster Bar & Seafood Tavern, 113 Main Street, the party goes on. This is your “Base Camp” before the run and where you can meet up with friends and family afterward. As a city institution for a long time, O’Brien’s is in a great spot for people to come back in from Main Street and City Dock, keeping the energy in one place and making it feel cozy.
People love the Timmie Metz Band’s live music, which keeps the party mood happy and fun from 12:30 PM to 3:00 PM at the after-party. You can expect a full house, lots of sing-alongs, and a happy mood that goes with the run’s bravery.
In O’Brien’s, you can warm up with hot food, hearty pub meals, and drinks that are good for the winter. After the run, most people go straight for something warm and comforting, like soups, bar classics, and hot drinks. This stop is as much about recovery as it is about having fun.
If you want to get a spot at O’Brien’s after the run, get there quickly. The after-party fills up quickly, and the band starts right on time.
Why it matters: The charity aspect
The Santa Speedo Run is more than just a show; it is a community-led drive for food and toys. Its goal is to spread holiday happiness while also collecting food for local families and toys and books for kids who need them. The run starts and ends at O’Brien’s on Main Street.
Over the years, organizers say they have gathered and given away thousands of toys to kids in the area. Since 2023, they have also been giving food to the Anne Arundel County Food Bank as part of their service. Over 500 runners usually show up for the event, which raises money and awareness all over downtown Annapolis.
During registration hours, bring a new, unwrapped book or toy and nonperishable food to O’Brien’s. You can also give cash or a check on the spot. Your donation helps kids and families in the area directly, and it keeps the tradition’s giving spirit front and center.
Conclusion: Are You Brave Enough?
The Santa Speedo Run, which is now in its 18th year, is one of Annapolis’s funniest and warmest events that happens every December. On December 13, 2025, at O’Brien’s Oyster Bar & Seafood Tavern, hundreds of runners will get together to jog through downtown wearing Speedos, Santa suits, and other holiday-themed clothes. Their goal is to raise money for toys, books, and food for local families.
It is not just a run at this event. You have to show up, cheer loudly, and give back. Whether you take part or just watch, you will be a part of a custom that is both funny and moving. People can easily walk the one-mile course, the after-party is fun, and the gifts help kids and families in Anne Arundel County.
Note December 13 on your calendar. Bring a toy and something fun to wear, and join the crowd, whether you are running, just looking, or just enjoying the fun. You can be brave, kind, and a part of something memorable at the Speedo Santa Run.