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Arts & Entertainment, Community, Do Not Miss

Do Not Miss List

August 19, 2025 by Piper Langenfeld

Week of 8/21 – 8/27

Presented by

Thursday, August 21 – Sunday, August 31 | Midnight Joe Look-Alike Contest | BD Provisions

Thursday, August 21 & Friday, August 22 | Cram the Cruiser School Supply Drive | Annapolis Mall 

Thursday, August 21 – Wednesday, August 27 | Watermark’s Annapolis Harbor & USNA Cruise | Annapolis City Dock

Thursday, August 21 | Open Mic Night | Rams Head Tavern

Thursday, August 21 | Hot Sips & Divorce Tips | Betty Center

Thursday, August 21 | Colonial Cocktails: Convict Cocktails | Historic London Town & Gardens

Thursday, August 21 | Live Music from Tim and Katie | O’Loughlin’s Restaurant

Friday, August 22 | Movies Under the Stars: In the Heart of the Sea | Bay Ridge Shopping Center 

Friday, August 22 | Summer Concert Series: 21012 Band & The Biondis | Goshen Farm 

Friday, August 22 | Timmie Metz Band & Tambo | Rams Head On Stage

Saturday, August 23 | Mr. Paca’s Garden Storytime: Plants Feed Me | William Paca House & Garden

Saturday, August 23 & Sunday, August 24 | Maryland Renaissance Festival | Crownsville Road

Saturday, August 23 | Watermark’s Annapolis Sunset Cruise with Live Music Featuring Steven Dunn | Annapolis City Dock

Saturday, August 23 | Morning Message with Spirit | Annapolis Crystals

Saturday, August 23 | The Washington Roast | Rams Head On Stage

Sunday, August 24 | Anchors & Artisans | Annapolis Town Center 

Sunday, August 24 | Puppy Plunge | Camp Letts

Sunday, August 24 | Nature Walk + Mindful Make | Yoga Barn

Monday, August 25 | School Skills for Preschoolers | Eastport-Annapolis Neck Library

Monday, August 25 | Savvy Women | CovingtonAlsina: Virtual

Monday, August 25 | Navy vs William & Mary Soccer Game | Glenn Warner Soccer Facility

Tuesday, August 26 | Southern Slavery in Colonial America | Historic Annapolis: Virtual 

Tuesday, August 26 | The Imaginary Invalid | Reynolds Tavern

Wednesday, August 27 | Annapolis Candidates Preservation Forum | William Paca House & Garden 

Wednesday, August 27 | Author Event: Madeline Martin | Park Books: Community Space

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Related posts:

Eye on Annapolis: Top 5 in the News | August 4 2025 | Summer Weekday Fun: A Budget-Friendly Itinerary for Kids Anne Arundel County Easter Events Guide 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:Navy Athletics Fall Preview: The Perfect Family Outing
Next Post:Eye on Annapolis: Top 5 in the News | August 18, 2025 |

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