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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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📸 Annapolis has no shortage of picture-perfect spots ✨

From charming downtown streets and waterfront views to beautiful gardens and scenic parks, we rounded up some of the best places around Annapolis for family photos, senior portraits, milestone moments, and capturing memories with the people you love 💛

If you’ve been planning updated photos or looking for a gorgeous local backdrop, this is one to save. What are some of your favorite photo spots? Comment below.

🔗 Full roundup is linked in our bio + below!
annapolismomsmedia.com/the-perfect-places-to-pose-the-best-spots-for-photos-in-annapolis/

#AnnapolisMoms #AnnapolisMD #VisitAnnapolis #FamilyPhotos #AnnapolisPhotographer
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