Annapolis Moms Deal Drop | Oct. 1, 2026
It might be the beginning of Spooky Season, but don’t forget that October is also Breast Cancer Awareness Month. Anne Arundel County offers no-cost cancer screenings to those who are …
The Ultimate Guide to Downtown Transit for Annapolis Moms
Our downtown Annapolis ultimate guide series continues. We investigated parking garages and compared meter prices. We braved all the public bathrooms. And now we’ve traversed Annapolis on both road and …
Our Fall Flavor Coffee Tour of Annapolis
Pumpkin Spice and Everything Nice! It’s that time of year—the start of the cozy season. We’re pulling our cardigans from the back of the closet and planning our apple picking …
Eye on Annapolis: Top 5 in the News | Sept. 29, 2026 |
A small group of Eastport residents protested the black-and-gray renovation of Mercedes-Benz of Annapolis, but the larger dispute centers on the City’s approval process. The Eastport Civic Association questions how …
Do Not Miss List
Week of 10/1-5 Thursday, October 1 Hamlet | Classic Theatre of Maryland (Oct. 1-18) Friday, October 2 Annapolis Area Christian School Presents the Annapolis Lower School Parent Preview Day | …
Fall Craft Fairs and Markets Around Annapolis
There’s something about fall and cooler weather that makes us want to shop local. You just can’t beat waking up early on a weekend morning, walking around with a coffee, …
Anne Arundel Jobs: One Local Hiring Event, Five Career Paths
Looking for your next opportunity? Anne Arundel County’s upcoming Fall Hiring Event brings employers from five high-demand industries together in one place, plus career resources to help job seekers take the next step.
Your Ultimate 2026 Fall & Holiday Guide
Fall in Maryland is packed with can’t-miss events festivals, but the fun doesn’t end with October! From parades and pumpkins to holiday markets, light displays and family-friendly traditions, there’s plenty …
Annapolis Pride Parade & Festival Returns With Family-Friendly Fun
Get ready to show your Pride, Annapolis! The Annapolis Pride Parade & Festival returns Oct. 3 with a parade through Annapolis followed by an afternoon of live music, food trucks, …
Save The Date List
Thursday, October 29 Live Arts Maryland Golf Classic | Bay Hills Golf Club Candlelight: A Haunted Evening of Halloween Classics | Maryland Hall A multi-sensory, Halloween-themed music experience. Die Laughing …