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Arts & Entertainment, Community, Do Not Miss

Do Not Miss List

August 31, 2025 by Piper Langenfeld

Week of 9/4-9/10

Presented by

Healthcare in Retirement

Thursday, September 4 | Oktoberfest Beer Release | Rams Head Tavern

Thursday, September 4 | Hot Sips & Divorce Tips | Betty Center 

Friday, September 5 | Summer Concert Series with 24 Karat & Laura Brino | Goshen Farm

Friday, September 5 | Watermark’s Naptown Brass Band Cruise | Annapolis City Dock

Friday, September 5 – Sunday, September 7 | An Ideal Husband | Colonial Players Theater

Friday, September 5 | Navy Football Block Party | Downtown Annapolis 

Saturday, September 6 & Sunday, September 7 | Kent Island Classic Pickleball Tournament | Mowbray Park 

Saturday, September 6 | Learning the Ropes | Hogshead Trades Museum

Saturday, September 6 | Car, Truck & Bike Show | Annapolis Moose Lodge #296

Saturday, September 6 | Warriors in the Park | Severna Park Taphouse

Saturday, September 6 | Navy Football vs UAB | Navy-Marine Corps Memorial Stadium 

Saturday, September 6 | Live Music from SRB Duo | O’Loughlin’s Restaurant 

Saturday, September 6 | Watermark’s Scandalous Annapolis Walking Tour | Market House Park

Sunday, September 7 | First Sunday Arts Festival | West Street

Sunday, September 7 | Libbey’s Crab Feast | Libbey’s Coastal Kitchen

Sunday, September 7 & Monday, September 8 | Open Auditions for A Christmas Carol | The Colonial Players Annex 

Sunday, September 7 | Beyond the Ropes | Kogen Dojo Annapolis

Sunday, September 7 | Upcycling: Make Your Own Paper | Historic London Town & Gardens

Monday, September 8 | Homeschool Hangout: Back to School! | Discoveries: Library at the Mall

Monday, September 8 | Generational Wealth Transfer | CovingtonAlsina: Virtual

Monday, September 8 | Skerryvore | Rams Head On Stage 

Tuesday, September 9 | Mr. Paca’s Garden Storytime: How to Read to a Grandma or Grandpa | William Paca House & Garden

Tuesday, September 9 | Homeschool Program: Colonial Espionage | Historic London Town & Gardens

Tuesday, September 9 | Sheena Easton | Rams Head On Stage


Wednesday, September 10 – Sunday, September 14 | Anne Arundel County Fair | Anne Arundel County Fairgrounds

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Related posts:

Save The Date List Eye on Annapolis: Top 5 in the News | August 25, 2025 | Meats on a grillMeat Me in Anne Arundel: Local BBQ You’ll Love The Blue AngelsThe Ultimate Annapolis Guide to Commissioning Week 2025
Category: Arts & Entertainment, Community, Do Not MissTag: Activities, Annapolis, Family Friendly See all posts by Piper Langenfeld

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BarterSaves is a proud community supporter of Annapolis Moms.
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