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Arts & Entertainment, Community, Do Not Miss

Do Not Miss List

October 14, 2025 by Piper Langenfeld

Week of 10/16-10/22

Presented by

Thursday, October 16 

Swing Into Action | Renditions Golf Course

Tractor Treat | Homestead Gardens: Davidsonville

Open Mic Night | Rams Head Tavern 

Colonial Cocktails: Spirits with the Spirits | Historic London Town & Gardens

Parenting in the Real World | Betty Center: Virtual

Steve Morse Band | Rams Head On Stage

Watermark’s and Historic Annapolis’ Special Historic Hauntings | 188 Main Street (Oct. 16-18)

Friday, October 17

Women in Business Networking Event | Trendy Tides Boutique 

Fall Into Wellness: A Journey of Resilience and Grace | Betty Center

Social Bridge | Captain Avery Museum 

Giselle | Maryland Hall (Oct. 17-19)

Station 7 Terror Trail | Arundel Volunteer Fire Department (Oct. 17 & 18)

Preschool Career Fair | Discoveries: Library at the Mall

FASO Golf Fundraiser | Severna Park Golf Center

Saturday, October 18

Trash to Treasures Rummage Sale | Pip Moyer Recreation Center

PRO-Vision Memorial Run | Severna Park Community Center

Invasive Plant Removal | Bacon Ridge Natural Area 

Annapolis Pride Parade & Festival | Downtown Annapolis

Plein Air Open House | Historic London Town & Gardens

Defenders of the Chesapeake: Maryland State Marines | Hogshead Trades Museum 

The Wine Festival | Kurtz’s Beach (Oct. 18 & 19)

Oyster Festival | Captain Avery Museum 

Bull & Oyster Roast | The Gunston School

Sunday, October 19 

Admissions Open House | The Gunston School

Mourning and Memory: Spirits of the Paca House | William Paca House & Garden 

In Gratitude: A Tribute to Earth, Wind & Fire and Sly & The Family Stone | Rams Head On Stage

Watermark’s Fall Foliage Bay Lighthouse Cruise | Annapolis City Dock

Monday, October 20 

22nd Annual AACS Golf Classic | Crofton Country Club

Women, Wine & Wisdom: Estate Planning | Federal House

Tuesday, October 21 

Ignite Annapolis | Maryland Hall

Major Developments in American Constitutional History | Historic Annapolis: Virtual 

Wednesday, October 22

Homeschool Day: Colonial Construction | William Paca House & Garden

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

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Sunday mornings done right ☀️🌸🍝

Spent the morning in West Annapolis bouncing between the sweetest local markets and honestly… we didn’t want it to end.

Started at the May Day Market - flowers everywhere, all the spring vibes, and the kids got to make the cutest little May Day baskets 💐✨

Then wandered over to the Annapolis Sons and Daughters of Italy Market and WOW… fresh baked goods, homemade everything, and Italian treats that felt straight out of Nonna’s kitchen 🇮🇹❤️ (yes, we left with cannolis… obviously)

Good food, local finds, and the kind of morning that just feels like spring
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