Our Guide to Memorial Day in Annapolis


Often determined to be the official jumping off point of summer, Memorial Day is the one time of year we all feel like kids again. The taste of popsicles and hot dogs, the smell of sunscreen and coconut-scented tanning oils, and the sights and sounds of parades, fireworks, and happy kids laughing out loud bring us back to our youth. These are just a few of the reasons we love this holiday as much as we do, and if you’re planning an Annapolis Memorial Day, following this guide to Memorial Day in Annapolis will amp up the wonderful to the highest level!

Unpacking, Exploring, and the Taste of Crab Cakes at Sunset

The three-day weekend starts out slowly with an exploration of your At Home Annapolis holiday escape; unpack your suitcases, bounce on the beds, and check out the views from ALL the windows in the house! Your long weekend has a lot of excitement in store for you, so for your first night in town we suggest a crab cake dinner at Acme Bar & Grill, located at 163 Main Street. Annapolis Memorial Day has never tasted this great!

Saturday Adventures on the Seas

Over the Annapolis Memorial Day Weekend, Pirate Adventures on the Chesapeake offers a military discount of 20% off; all you need to do is show your Military ID and let the seas be your mistress for the day! Offering face painting, canon fights, and of course, a real pirates’ treasure, this child’s adventure will be just as fun for the adults who are chaperoning. We promise they won’t make you walk the plank! This deal lasts all weekend, so if you have other things in mind for Saturday, you won’t have to miss out; you can just go on Sunday or Monday instead!

Sunday Fun Day

Geek Pride Day also happens to fall on Memorial Day Weekend in 2019 (May 25th in honor of the premiere of the first Star Wars), and their online 5K and 10K events can be completed this weekend as well without fighting the crowds. Sign up for $20 (proceeds go to Pencils of Promise Charity) and walk, run, or jog your way to a medal engraved with a special Sheldon Cooper quote—all you have to do is report your finishing time to the king geeks!

The Reason for the Annapolis Memorial Day Weekend

Memorial Day isn’t just the starting pistol for summer; it’s the day we honor those heroes who have sacrificed everything in the fight to keep our country free, and our Annapolis Memorial Day Parade is our way of showing we will never forget. Starting at 10 AM and taking place downtown, this convoy of floats, vehicles, marching bands, and so much more lets our American pride shine strong with this salute to our American heroes.

Comfortable, Stylish, and All-American

Your Annapolis getaway will shine even brighter when you choose to stay in one of our classic All-American cottages and homes. Reserve yours today! If you’re visiting Annapolis during Commissioning Week, view our best Commissioning Week weekly rentals, condos, or lodging rentals!

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