October 2-5: Annapolis Power Boat Show returns to the City Dock in Annapolis, MD. This premier event showcases the latest in boating and marine innovations, with hundreds of boats on display, educational seminars, and fun activities for the whole family.

October 4: Oktoberfest at The Wharf will take place from 2-7pm. THead to The Wharf to celebrate Oktoberfest—featuring the Wiener 500 Dachshund Dash, Polka on the Pier, and the Sam Adams stein hoisting competition.

October 9-12: Annapolis Sailboat Show will take place at the City Dock in Annapolis, MD. This event is dedicated to sailing enthusiasts and features a wide range of sailboats, marine gear, and educational seminars.

October 17-19: Boo At The Zoo will be held at the National Zoo from 6-9pm (last entry at 8:30pm). This family-friendly event features trick-or-treating, animal encounters, and festive activities.

October 25: International Gold Cup will be held at Great Meadow in Virginia.

November 1: Día de los Muertos will be held from 4-7pm at The Wharf. Celbrate the Day of the Dead. This family-friendly afternoon will include live music by La Unica, cultural performances, a Modelo beer gardens, face painting, sugar skull decorating, a community lantern procession, and more.

December 6: Holiday Boat Parade & Party at The Wharf DC. Event ends in fireworks! Celebrate the holidays with this iconic DC event that features over sixty beautifully decorated boats parading along the Washington Channel.

June 14-16: Clipper Round the World Yacht Race Clipper 2025-26 Race Stopover at The Wharf DC which will once again be a host port.