It’s the Great Pumpkins, Annapolis
Annapolis is fall-ing for pumpkins all over again! The Great Annapolis Pumpkins have returned this October, turning downtown into a festive, photo-worthy pumpkin patch filled with giant gourds that would …
Annapolis Pride Parade Is Back and Ready to Slay
Annapolis, get ready to strut your stuff! The Annapolis Pride Parade & Festival is back for its fifth year, set for October 18, 2025. Each year, families, friends, and allies …
Eye on Annapolis: Top 5 in the News | October 6th, 2025 |
Annapolis Police are investigating a fatal scooter crash on West Street near Brewer Avenue after 27-year-old Samuel Sheeder of Annapolis struck a curb on September 28, 2025; he was transported …
Do Not Miss List
Week of 10/9-10/14 Presented by Thursday, October 9 Bring a Friend Week with Chesapeake Youth Symphony Orchestra | Maryland Hall Annapolis Sailboat Show | Annapolis City Dock (Oct. 9-12) Watermark’s …
Haunted Happenings in Annapolis
Annapolis is full of charm year-round, but come October, our historic streets take on a delightfully eerie twist. Cobblestone alleys, flickering lanterns, and centuries-old buildings set the stage for a …
Get Lost in Maryland Corn Mazes
Fall in Maryland is a-MAZE-ing! It’s prime time for one of the season’s most beloved traditions: corn mazes! These giant puzzles formed in fields of towering stalks turn ordinary farms …
Save The Date List
Presented by Wednesday, November 5 Full Moon Tour | Hammond-Harwood House Watermark’s Annapolis Harbor & USNA Cruise | Annapolis City Dock (Nov. 5-9) Thursday, November 6 Philadelphia’s Fairmount Park Historic …
Trunk or Treats Around Annapolis
Halloween is better when the candy comes to you! These community events let kids show off their costumes, collect candy, and enjoy festive fun all in one safe spot. From …
Picking the Perfect Pumpkin Patch
While Starbucks has had their Pumpkin Spice Latte out for more than a month, we’re in full pumpkin mode now. Sure, Trader Joe’s has conveniently displayed awesome (and unique) pumpkins …
Eye on Annapolis: Top 5 in the News | September 29th, 2025 |
Anne Arundel County Public Schools placed most Annapolis cluster schools into “secure status” after police activity near Tyler Heights Elementary, emphasizing there was no school threat and students and staff …