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Arts & Entertainment, Community, Do Not Miss

Save The Date List

September 19, 2025 by Piper Langenfeld

Presented by

Wednesday, October 22 

Homeschool Day: Colonial Construction | William Paca House & Garden

Friday, October 24

Social Bridge | Captain Avery Museum

Thomas Dolby: “The Iconic 80s” | Rams Head On Stage

Dracula: A Comedy of Terrors | Colonial Players Theater (Oct. 24-Nov. 15)

Pumpkin Walk | Hammond-Harwood House

Navy Women’s Soccer vs Lafayette Game | Navy-Marine Corps Memorial Stadium

Spooky Crafts and Spirited Cocktails | Chesapeake Arts Center

Movies Under the Stars: Moana 2 | Bay Forest Shopping Center

West Side Story | Children’s Theatre of Annapolis (Oct. 24-Nov. 9)

Bountiful Harvest: Costumes & Cocktails | The Atreeum at Soaring Timbers

Watermark’s Annapolis Harbor & USNA Cruise | Annapolis City Dock (Oct. 24-Nov. 1)

Saturday, October 25

Halloween Outdoor Market | Wildberry Farm 

Mr. Paca’s Garden Storytime: Trick or Treat on Scary Street | William Paca House & Garden

Navy Football vs FAU (Homecoming) | Navy-Marine Corps Memorial Stadium 

Fall Fun Fest | A Little Farm and Nursery (Oct. 25-26)

MD Corn Maze | Gambrills Road (Oct. 25-Nov. 2)

Watermark’s Cruise to OysterFest in St. Michaels | Annapolis City Dock

Corsets and Contraband: African American Women’s Labor in the Fight for Freedom | Hogshead Trades Museum

O’Halloween Party | O’Loughlin’s Restaurant

Sunday, October 26

Anchors & Artisans | Annapolis Town Center

Holiday Craft Fair | Earleigh Heights Fire Department

Messages from Spirit with Two Mediums | 158 W Lake Drive

Monday, October 27 

Women & Investing | CovingtonAlsina: Virtual

Tuesday, October 28

Iam Tongi | Rams Head On Stage

Friday, October 31

Halloween Celebration | Federal House 

Social Bridge | Captain Avery Museum

Friday, October 31 & Sunday, November 2 | Don Giovanni | Maryland Hall

Saturday, November 1

Muay Thai Amateur Athletic Circuit | Chesapeake Christian Fellowship 

Stride for SPAN 13th Annual Turkey Trot 5K/1M | Kinder Farm Park

Past Life Regression with Sound Bowls | 158 W Lake Drive 

U.S. Colored Troops in the Civil War | Hogshead Trades Museum

Brewer Hill Cemetery Tour | Brewer Hill Cemetery

Sunday, November 2 

First Sunday Arts Festival | West Street

Richard Thompson | St. John’s College

Macy Gray: On How Life Is 25th Anniversary Tour | Rams Head On Stage

Don Giovanni | Maryland Hall

Admissions Open House | The Gunston School 

Honoring Maryland’s Emancipation Day | Museum of Historic Annapolis

Monday, November 3

Retirement Homestretch | CovingtonAlsina: Virtual

Tuesday, November 4

Mr. Paca’s Garden Storytime: Federico and the Wolf | William Paca House & Garden Micky Dolenz Of The Monkees: Songs & Stories | Rams Head On Stage

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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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Spring break idea loading… ⚓️🌸

If you’re looking for an easy, fun way to get out of the house with the kids, the @annapolismaritimemuseum & Park is such a great little outing! We visited over the summer, but it’s just as perfect for a quick spring break adventure, especially when you need something to break up the day.

It’s super educational (without feeling like it 🙌) and packed with interactive exhibits that keep little hands and minds busy. Plus, you can explore at your own pace, making it a low-stress win for moms.

✨ Pro tip: Make it extra fun with a stop at @blackmarketbakers for a fresh baked treat before or after because every outing deserves a little something sweet.

Save this for your spring break plans and add it to your list! 💛
What are your plans this spring break with your kiddos?
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We are so excited to

We are so excited to introduce Riptide Remodeling LLC as a new Community Supporter! The owners are so great and believe that you don't have to overpay to get amazing quality work. If you are in need of any remodeling project you need to get a bid from Riptide Remodeling LLC!

"Too often, we see homeowners end up paying twice because a bathroom wasn’t done right the first time by the contractor.

These problems don’t always show up right away, but when they do, repairs can be costly.

That’s exactly why we do things differently.

Our work is built to last, with the right materials, proper preparation, and real warranty support.

We believe a remodel should last - not become the next repair.

Message us for a FREE design consultation to get started."
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