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Arts & Entertainment, Community, Do Not Miss

Do Not Miss List

September 14, 2025 by Piper Langenfeld

Week of 9/18-9/22

Presented by

Thursday, September 18 – Sunday, September 21 | PopUp! Inflatable Art Festival | Pikesville Armory

Thursday, September 18 | National Cheeseburger Day | Federal House

Thursday, September 18 | TNF Bills vs Miami and Live Music from Tim & Katie | O’Loughlin’s Restaurant 

Thursday, September 18 | Colonial Cocktails: Medicinal Mixers | Historic London Town & Gardens

Friday, September 19 | Women in Business Networking Event | Trendy Tides Boutique & Annapolis Crystals

Friday, September 19 | For the Love of the Library | Busch Annapolis Library

Friday, September 19 | Calm for a Cure Launch Party | Pherm Brewing Company 

Friday, September 19 | Baygrass Kickoff Party | Maryland Hall

Friday, September 19 | Watermark’s Annapolis Sunset Cruise with Chris Sacks (Duo) | Annapolis City Dock

Saturday, September 20 & Sunday, September 21 | Gun and Knife Show | Anne Arundel County Fairgrounds 

Saturday, September 20 | Solar Eclipse in Virgo Past Life Regression | 158 West Lake Drive 

Saturday, September 20 | Mr. Paca’s Garden Storytime: Library Girl | William Paca House & Garden

Saturday, September 20 & Sunday, September 21 | Women’s Work Weekend | Historic London Town & Gardens

Saturday, September 20 | March to Revolution | Pinkney Street

Saturday, September 20 & Sunday, September 21 | Annapolis Baygrass Music Festival | Sandy Point State Park 

Saturday, September 20 | Navy Women’s Soccer vs Boston University Game | Navy-Marine Corps Memorial Stadium

Saturday, September 20 | Boatyard Beach Bash | Annapolis Maritime Museum

Saturday, September 20 | Maysa | Rams Head On Stage

Saturday, September 20 | Watermark’s African American Heritage Tour | Market House Park 

Sunday, September 21 | Muaythai Development League | Benfield Sportscenter

Sunday, September 21 | Together in Teal | Annapolis Mall

Sunday, September 21 | Annapolis Italian Fall Festa | Sons and Daughters of Italy

Sunday, September 21 | Inaugural Corn-Hooley & Shamrock Shenanigans | Earleigh Heights Fire Station

Sunday, September 21 | Music of the Americas | Maryland Hall 

Sunday, September 21 | Ballet in the Garden | Hammond-Harwood House 

Sunday, September 21 | Comedian Michael Yo | Rams Head On Stage

Sunday, September 21 | Priddy Music Academy Performance | Market Space at Federal House

Monday, September 22 | Retire on Purpose | CovingtonAlsina: Virtual

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Category: Arts & Entertainment, Community, Do Not MissTag: Activities, Annapolis, Family Friendly See all posts by Piper Langenfeld

About Piper Langenfeld

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Summer can bring a lot of joy- but it can also bring stress, transitions, and unexpected challenges for children, teens, and families.

Our community supporter, The Collective Healing Center, offers counseling and support services designed to help individuals and families navigate life's ups and downs with confidence, resilience, and compassion. Their experienced therapists work with clients of all ages, providing a safe and supportive space for healing, growth, and emotional well-being.

Prioritizing mental health isn't only important during difficult times—it's an essential part of living a healthy, balanced, and connected life.

Learn more about their services and approach:

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The Collective Healing Center | Comprehensive Mental Health Services in Annapolis

www.thecollectivehealingcenter.com

The Collective Healing Center in Annapolis is an evidence-based private practice. Offering trauma-informed therapy for individuals, families, and groups to foster healing and growth.
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