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Calendar of Events in Annapolis

Year Round, there's something going on in Annapolis - Here's a Summary

There is always something going on in Annapolis, and we can always recommend many activities  to do no matter the time of year or day of the week….

So here we go with an annual calendar of events .  Always consult with us for actual dates and we can get you booked in.  This is not an all-inclusive list, we can always advise of additional events plus all ongoing activities that we list on our Things to Do page


Polar Bear Plunge – Thousands of crazy people expose themselves to hypothermia for a great cause, Special Olympics.  20 minutes away at Sandy Point State Park


Annapolis Restaurant Week

St Patrick’s Parade – This is a BIG deal in town, biggest parade of the year,  Held on Sunday before weekend before St Paddy’s day… so early (March 8-ish)

Annapolis Film Festival

Annapolis Oyster Roast & Sock Burning – a great locals event.  Celebrates beginning of spring and sailing season.  Buy tickets in advance ~3rd Saturday in March

Maryland Day – March 26 – Our state’s birthday! There are all sorts of events happening all over the town and the state


Annapolis Book Festival

Spring Sailboat Show – a mini version of the gigantic fall sailboat show, this still attracts a big crowd. Preceded by power boat show on Kent Island previous week

Bay Bridge Boat Show –  the mini version of fall powerboat show

Boat Maryland Week

St John – USNA Croquet Match – another great quirky local Annapolis event.  Don’t bet against St John’s! Buy tickets way in advance


May Day Baskets – May 1 – another local tradition – front doors adorned with lovely fresh flower baskets

Wednesday Night Sailboat Races – Huge tradition, every Wednesday through to late September. Best way to view is to get a ride on the Schooner Woodwind

First Sunday Arts Festival – great show – see our blog

USNA Commissioning Week – THE event of the year (ok Boat show is big big too)  Includes Blue Angels Tu-Wed. Families book way ahead.  We do have 2021 openings though

Dinner Under the Stars – Each and every Wednesday night May thru September.  West St closes down for a nice evening of music, food and drink


Annapolis Arts Week & Paint Annapolis – there are people painting literally anything and everything around town…

Summer Concert Series – Sunday & Tuesday City Dock, Thursday night Maritime Museum, Quiet Waters Park


4th of July Fireworks & Parade

Water Taxi, Schooner Woodwind & Watermark Tours & Cruises – all summer long!


Renn Fest – One of the country’s biggest Renaissance Festivals .. Thru October

World’s Largest Crab Feast

Annapolis 10 Miler – right past our front door!


Navy Football – select weekends  September – November – arrive early for the pre-game pagentry

Maryland Seafood Festival – Sandy Point State Park

Kunta Kinte Heritage Festival – City Dock


US Powerboat & US Sailboat Shows – consecutive weekends on first two weekends of October.  The granddaddies of all US Boat shows for over 50 years

Oyster Festival


Maritime Republic vs. Annapolis Tug of War – another great quirky tradition – great party in Eastport!

Annapolis by Candlelight – tours of Historic Annapolis homes.  Runs through Christmas on weekends

10k across the Bay – Marty did this all 5 years- 22,000 runners and walkers on a unique one way trip across the Bay Bridge


Grand Illumination – Annapolis Tree Lighting – right out of a Hallmark movie

Chocolate Binge Festival – arrive early!

Midnight Madness Holiday Shopping – the first 3 Thursday’s in December – lots of deals and Christmas Spirit

Eastport Yacht Club Boat Parade – all sorts of decorated boats entertain you –

Military Bowl – college bowl game

New Year’s Eve in Annapolis



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