The Annapolis Cup Croque Match is a community-wide event that takes place each spring between St. John's College and the U.S. Naval Academy. The two schools attract thousands of people on the front lawn of St. John's for a festive lawn party complete with costumes, picnics, swing dancing, and a croquet competition.

Shed yourself of winter and celebrate spring at the annual Annapolis Oyster Roast & Sock Burning. At the beginning of boating season each March, Annapolitans gather to burn their winter socks, shuck oysters, and enjoy live music. Fun activities are offered at the festival, including electric boat tours of Back Creek.

The Annapolis Film Festival was established in 2013 as a place for filmmakers to showcase different global perspectives and independent thought to a wide audience. The festival showcases more than 70 films annually.

The annual Maryland Avenue Earth Day Festival features antiques, arts, and crafts. The event is held in the historic district of downtown Annapolis between the State House/State Circle and the United States Naval Academy.

Honor the legacy of Rev. Dr. Martin Luther King, Jr. at the 6th Annual City of Annapolis Rev. Dr. Martin Luther King Parade. Businesses from all over Maryland will converge in Downtown Annapolis and parade from Amos Garrett's Blvd down West St then Main St to City Dock.

On May 1, the doors of homes and businesses are adorned with baskets full of fresh-cut flowers and colorful ribbons to compete for winning ribbons and an invitation to the Garden Club's Annual Tea.

Shop with over 130 artists on the first Sunday of each month May through November in downtown Annapolis Maryland from 11am to 5pm except November which is 11am to 4pm.