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Annapolis Moms Deal Drop | Oct. 22, 2026
This October is flying by, and we’re coming up on Halloween. If you’re looking for costumes (and your nearby stores have …
Dinner’s Covered! Easy Family Takeout Meals in Annapolis
Between school drop-offs, work, errands, and shuttling the kids from one practice to the next, weeknights can get pretty …
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Best Places to Take Fall Family Photos in Annapolis
The temperatures keep bouncing up and down. There’s been a storm or two. But we are well into the fall season. As we …
Secondhand Style: Where to Thrift and Shop Vintage in Annapolis
The resale market for clothes, shoes, and accessories has exploded in recent years. Fast fashion has made some people …
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Do Not Miss List
Week of 10/22-28 Thursday, October 22 Spilling Pictures Presents The Live Spill | 49 West Coffeehouse, Winebar & …
Maryland Women Are Starting More Businesses. What’s Driving the Shift?
Women are responsible for 58% of new Maryland businesses launched since 2019. A new state report explores why more women …
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Eye on Annapolis: Top 5 in the News | Oct. 20, 2026 |
Two data breaches affecting Anne Arundel County have renewed concerns about cybersecurity, the protection of sensitive …
Porchfest Annapolis Returns Oct. 24 With Free Live Music in Murray Hill
Get ready for an afternoon of live music, neighborhood charm, and community fun! Porchfest Annapolis is back for its …
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Fall Theater, Comedy and Live Performances in Annapolis and Beyond
Looking for something different to do this fall? From Broadway musicals and classic plays to stand-up comedy and live …
Annapolis Moms Deal Drop | Oct. 15, 2026
Not only will Annapolis Moms keep sharing the best local deals, but we’ll also always have some exclusive discounts from …
Pumpkin Spice and Everything on Ice: An Annapolis Fall Pub Crawl
It’s time to trade orange crushes for pours that taste like autumn in a pint glass! We’re taking you on a fall-flavored …
Do Not Miss List
Week of 10/15-21 Thursday, October 15 Great Annapolis Pumpkins | Downtown Annapolis (Oct. 15-30) Middle School Visit Day …
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Upcoming Events
Events
List of events in Photo View
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Maryland Corn Maze
September 12 - November 8 -
Great Annapolis Pumpkins
October 5 - October 30 -
Locally Gathered HERE. a pop-up shop
October 16 - November 8
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💙 Community Supporter: A Team Family Law, LLC
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Before making major financial decisions, take a step back and get informed. The right guidance can help you protect your interests and move forward with confidence.
When you’re ready to talk through your unique situation, A Team Family Law, LLC is here to help with real talk and no judgment. 💬
📞 Schedule a consultation and get the guidance you deserve.
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8 WAYS TO SPEND YOUR WEEKEND AROUND ANNAPOLIS 👀
Live music, Halloween events, fall festivals, and a classic spooky tale on stage, there’s plenty happening around Annapolis from October 22–25!
Here’s what’s on the list:
🎶 The Live Spill at 49 West
🎃 KMA Law Office’s Halloween Spooktacular
🍬 Blue Crab Cupcakes’ 5th Annual Trunk or Treat
🎭 The Legend of Sleepy Hollow at The Colonial Players
🌽 Fall Fest at Greenstreet Gardens
🎸 Porchfest around Annapolis
🐾 Trick or Treat Trail at the SPCA
🎻 Naptown Philharmonic Orchestra’s Halloween Spooktacular
Plus, there’s more to explore throughout the weekend!
👉 See the full list here:
annapolismomsmedia.com/do-not-miss-list-oct-22/
#AnnapolisMoms #DoNotMissList #AnnapolisEvents #FallFun #WeekendPlans
Greenstreet Gardens @bluecrabcupcake @aacspca
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