Annapolis Events 2021

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Annapolis, Maryland, nestled alongside the beautiful and bountiful Chesapeake Bay, offers a delightful array of things to see and do. You can shop until your heart’s content, dine in one of many deliciously tasteful seaside restaurant venues or enjoy its engaging events offered all year long. Hopefully, in 2021, we will once again be able to take part in all of the annual Annapolis events we anxiously anticipate, including…

The New Year’s Day Resolution Run; and we know we will be able to take part in the February 26th Virtual Annapolis by Candlelight Tour! The latter is a “crisp autumn day walk” through historic Annapolis, on which visitors can revel in the cultural heritage and historic preservation of Maryland’s state capital. Historic buildings in all their glorious grandeur and some of the most beautiful homes in Annapolis will open their doors and invite participants “inside”.

Did you know that on St. Patrick’s Day, every bar in Annapolis is Irish? We wish you the luck of the Irish so that you will get to visit then!

Later, in May, the Wednesday Night Sailboat Races begin. June is time for our merry Irish Festival. Then, in July, enjoy fireworks on the fourth and the third Sunday Music Festival.

August is the month we all like to enjoy our Annual Annapolis Art Walk and the Annapolis Crab Feast. The Annual Labor Day Parade and Annapolis Fall Festival are held in September; and in October, we look forward to the Annapolis Parade of Boats, Oktober Fest in Annapolis and the Annapolis Halloween Festival.

Celebrate the local Annapolis art scene at the Arts between the Creeks event in November and then on to our Annapolis Holiday Tree Lighting Ceremony in December and a spectacular fireworks display on New Year’s Eve.

To be safe, just check with event organizers before you head out to be sure that COVID hasn’t put a kibosh on things!


Gary Wells

Owner of Window Expressions, Annapolis' premier custom window treatment specialist. With years of of experience in the industry, Gary takes pride in his keen eye for design and his ability to transform clients' visions into reality. He finds joy in leading a local, family-owned business committed to putting the "custom" in customer service.

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