35th Annual - "Johnnies" & "Mids" vie for the coveted Annapolis Cup. Croquet match brings together two institutions for what SI says has "no parallel in intercollegiate sports." Dress "Great Gatsby" style. $15.00 Advance Sale General Admission tickets. (12 and under Free) No tickets will be sold at the gate. Current St. John’s students and [...]
Antique, arts, and craft vendor space is available for this annual event. Maryland Avenue is located in the historic district of downtown Annapolis between the State House/State Circle and the United States Naval Academy. It's a green twist on a local tradition, featuring old-fashioned street festival atmosphere with green exhibitors, merchants and vendors offering art, [...]
The 63rd annual May Day basket competition, sponsored by the Garden Club of Old Annapolis Town, will be held May 1st in celebration of May Day. Residents and merchants in throughout the City will arrange baskets of fresh cut flowers to display outside their homes and businesses throughout the day. Displays will be out by [...]
Free Comic Book Day at Third Eye Comics Annapolis: Join us for our annual free Comic Book Day + 11 years of Third Eye Comics. Choose from more than 30 free comics plus other free swag, creator guests, super sales and more.
Celebrate the Kentucky Derby at Two Great Houses of Colonial Annapolis! Annapolis gained fame in colonial times as the first site of city-organized horse racing. On the fairground north of West Street, George Washington and other leaders came to watch the races Race Week was a social highlight renowned throughout the colonies. Reservations encouraged. $50 per [...]
George Washington came to Annapolis for the horse racing; be like George and come to Derby Fest. Watch the Kentucky Derby, enjoy good food and drink, games, a hat-making table, tours of two colonial homes and more. Cash Bar, 21+ only George Washington came to Annapolis for the horse racing; be like George and come [...]
Enjoy a beautiful walk through Quiet Waters Park with your favorite furry friend. Explore the large outdoor vendor and food festival. It's fun for families of all ages. Pledge to walk and help the animals of the AACSPCA.
Welcome to First Sunday Arts Festivals in Annapolis, Maryland. We invite you to visit the festivals on the first Sunday of each month May through November in downtown Annapolis Maryland from 11am to 5pm to shop over 130 artists. Located at the first block of West and Calvert Streets. Admission is free!
Take a piece of the William Paca Garden home with you! Choose from among more than 300 varieties of perennials, annuals, vegetables, herbs, trees and shrubs – including heirloom and “cutting-edge”, native and exotic – that have been raised by Paca Garden volunteers. Gardeners on hand to answer questions. Information-packed catalog available online or for [...]
Our Mother’s Day Brunch Sail departs Annapolis for a three-hour Brunch cruise at 10:00 am and returns at 1:00 pm. Sailing cruise includes one free Bloody Mary or Mimosa and delicious food $94 per person, $54 per child. Maximum 35 guests.