Downtown Annapolis Maryland loves Festivals and Events. This is a great town to visit and stay entertained with history, arts, sailing, sports and fun festivals. There is always something to do in Annapolis Maryland.

Downtown Annapolis Maryland Festivals

First Sunday Arts festivals are held on the first Sunday of every month (May to October) from noon to 5pm on Calvert and West Streets. The streets and parks in this area are filled with over 100 artists and crafters, live music, dance, street performers, and international outdoor cafes. This is your chance to buy unique and original local made in the area arts and crafts. Admission is always free and plenty of free parking is available  at the State Parking Garage on the corner of Calvert and Bladen streets. Friendly pets are welcome so bring all your friends and family to this fun filled monthly street festival. Arrive early and enjoy Sunday Brunch in one of the many restaurants on West Street and stay after the festival and take in a show at Rams Head On Stage or 49 West coffeehouse and Gallery. Details for each months events are at

Spring and Fall Festivals on Maryland Avenue are a long time Annapolis tradition. The stores spill out on to the streets plus add entertainment and it becomes a great place to hang out and shop at the streets many boutiques. Start at the Statehouse and work your way down Maryland Ave. Free Admission

Eastport a Rockin  If you love local musicians this is the  place for you. Just across Spa Creek in Eastport you will be entertained every June while supporting local musicians. See website for ticket sales.

Summer at City Dock will keep you entertained every Sunday afternoon in summer as you overlook Spa Creek. Keep up to date of the many family friendly events at Arrive early to the City Dock on Sundays for the farmers market for local farm fresh food. Both events are free admission.

Oktoberfest in the Village of West Annapolis is the first Sunday in October from 10am to 5pm. Lots of vendors, beer and food plus a stage of traditional german music. Free admission.

There is always something going on in Annapolis Maryland with more festivals and fairs just outside of downtown Annapolis plus a list of events to huge to post on any message board.

The best local Annapolis calender of events are: visitors center , Bay Weekly , Capital Newspaper , What's Up Annapolis.