From Turkey Trots to Jingle Bells: Holiday Runs Around Annapolis
Turkey trots are an annual tradition dating back to 1896 in Buffalo, New York, when the local YMCA hosted a footrace with only six participants. Nowadays, these holiday runs have …
Halloween Parties Around Annapolis for Kids and Adults
Costumes? Check. Candy buckets? Check. A calendar full of spooky fun? We’ve got you covered! Halloween is almost here, and Annapolis and the surrounding area are packed with ways to …
No Tricks, All Treats at Annapolis Trunk or Treat Events
Halloween might only be one night a year, but it’s not the only time for your kids to wear costumes and score some candy. There are lots of events happening …
Jumbo Jack-o’-Lanterns: The Great Annapolis Pumpkins
This October, the narrow streets of Annapolis will have some very large guests. The Great Annapolis Pumpkins are half-ton gourds so gargantuan that they’re almost fit for a carriage. And …
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 …
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, …
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 …
The Ultimate Guide to Fourth of July Fun in and Around Annapolis 🎆
Nothing says “freedom” like sweating through a flag tee while chasing your kids down a parade route with a half-melted freeze pop in one hand and a folding chair in …
Annapolis Juneteenth Celebration Returns for Sixth Year
After uncertainty over whether the celebration would happen this year, the Annapolis Juneteenth celebration is moving forward with a message centered on healing, history and community. Now in its sixth …
Annapolis Father’s Day Gift and Experience Guide
Yes, we are Annapolis MOMS, but we still love our dads! With Father’s Day coming up on Sunday, June 21, we know many families are looking for fun and thoughtful …