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 …
Annapolis Moms Want Brunch for Mother’s Day
We usually write for moms on this website, but today we’re talking to the people who love them: spouses, kids, grandkids, and anyone else who loves a mother figure in …
Celebrating May Day: The Evolution of a Long Annapolis Tradition
For 70 years, on May 1, the streets of Annapolis have burst into color as residents and businesses alike take part in the beloved May Day tradition. What began as …
Easter Brunch in Annapolis
If your Easter plans involve mimosas, something sweet and maybe not cooking for a crowd, you are in luck. Annapolis restaurants are doing what they do best this weekend: serving …