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 …
Fall on Tap: Brews and Bites in Annapolis
It’s time to trade orange crushes for pours that taste like autumn in a pint glass. Fall in Annapolis is a craft beer lover’s dream! The air is crisp, the …
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 …
Taco Tastings: Where to Find Your Taco Fix in Annapolis
Tacos are for more than just Tuesdays! They’re the perfect, anytime meal, any day of the week! Known for being incredibly versatile, easy to eat, and packed with flavor, tacos …
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 …