Cherished Traditions: Annapolis’ Most Beloved Annual Events

For such a small city, Annapolis sure knows how to throw a good party – and they frequently do. Here’s a brief list of some of our absolute favorite events in downtown Annapolis that you won’t want to miss. Be sure to check out the Visit Annapolis website for a thorough list of all of the events in the city, from Maryland Day to the Pride Parade, a Juneteenth celebration, and more!

Annapolis Boat Shows

1. Annapolis Boat Shows

Fifty years ago, Annapolis hosted the first in-water sailboat show that has today become one of the world’s most popular. These in-water sail and powerboat shows allow you to board the latest boat models, research and purchase boating equipment, weather gear, charters and anything else a boater might need. Part boat show, part multi-day party, downtown Annapolis comes alive when the boat shows are in town.

Sailboat show: April & October
Powerboat show: October

Navy Football Games

2. Navy Football Games

Navy football season is practically a city-wide holiday in Annapolis. Come and enjoy pregame tailgates, competitive football, and fun downtown Annapolis after parties that residents look forward to all year long. Can’t make it to the stadium? Head to Dock Street Bar and Grill, one of our favorite spots that is sure to have the game on.

View the Navy football schedule.

Slaughter on the Water: Tug-o-War

3. Slaughter on the Water: Tug-o-War

This hilariously fun annual event is a local favorite, and one not to be missed! Since 1997, a tug-o-war has taken place between the Maritime Republic of Eastport and the city of Annapolis as a real-life farcical representation of colonial power struggles. No matter which side wins, Eastport always has the better party.

2023 Date TBD

4. Fourth of July Weekend

 Annapolis makes the 4th of July a multi-day celebration with a parade, events, and an amazing fireworks show with multiple vantage points. Getting out on the water is by far the best way to see them, which includes the rooftop deck of your FLOHOM. Capital SUP also hosts a 4th of July paddle, but be sure to try and book in advance.

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