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Arts & Entertainment, Community, Do Not Miss

Do Not Miss List

June 16, 2026 by Piper Langenfeld

Week of 6/18-6/24

Presented by

Thursday, June 18

Anne Arundel County Firefighters’ Emerald Society Presents A Night for Brian | Brian Boru Irish Pub & Restaurant

Juneteenth VIP Gala | Fresh Start Life Center

Yappy Hour | Capital SUP Eastport

Friday, June 19

Antique & Classic Boat Festival and Coastal Arts Fair | Chesapeake Bay Maritime Museum (June 19-21)

Annapolis Recreation & Parks Presents the Carr’s Beach Reunion | Annapolis Maritime Museum: Park Campus and Carr’s Beach Park

Saturday, June 20

The Oddities & Curiosities Expo | Baltimore Convention Center (June 20-21)

Stories in the Gallery | Chesapeake Arts Center 

Annapolis Juneteenth Parade | St. John’s College

Annapolis Juneteenth Festival | Bates Athletic Complex

Shane McAnally | Rams Head On Stage

Y.A.R. Presents the DMV R&B Wine Festival | Anne Arundel County Fairgrounds 

Sunday, June 21

Father’s Day Celebration | Rams Head Tavern 

Makers of Maryland Presents the Anchors & Artisans Pop-Up Market | Annapolis Town Center 

Richmond Flying Squirrels vs Chesapeake Baysox | Prince George’s Stadium 

Annapolis Blues vs. Virginia Beach United (W) | Navy-Marine Corps Memorial Stadium

Annapolis Blues vs. Northern Virginia FC (M) | Navy-Marine Corps Memorial Stadium

Timmie Metz Presents Stapleton | Rams Head On Stage

Monday, June 22

Birds on a Wire Art Workshop | Julep Kitchen & Bar

Tuesday, June 23

Historic Annapolis Presents Mr. Paca’s Garden Storytime: Rafa Counts on Papá | William Paca House & Garden 

Annapolis Blues’ International Friendly | Navy-Marine Corps Memorial Stadium 

Wednesday, June 24

Sail250 Maryland & Airshow Baltimore | Various Locations

Annapolis Blues vs. VDA (W) | Navy-Marine Corps Memorial Stadium 

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Related posts:

Eye on Annapolis: Weekly Round-Up Save The Date List The Ultimate Annapolis Guide to Commissioning Week 2026 Eye on Annapolis: Weekly Round-Up
Category: Arts & Entertainment, Community, Do Not MissTag: Activities, Annapolis, Family Friendly See all posts by Piper Langenfeld

About Piper Langenfeld

Previous Post:Annapolis Juneteenth Celebration Returns for Sixth Year
Next Post:Eye on Annapolis: Top 5 in the News | June 17, 2026 |

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Join the Chesapeake Baysox on Sunday, June 21 for our Father's Day BBQ featuring a two-hour all-you-can-eat buffet with flank steak, Old Bay roasted chicken, a sausage bar, mac & cheese, desserts, and more before Baysox baseball at 1:05 PM.

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