Pumpkin Spice and Everything on Ice: An Annapolis Fall Pub Crawl
It’s time to trade orange crushes for pours that taste like autumn in a pint glass! We’re taking you on a fall-flavored pub crawl through the streets of Annapolis, where …
10 Free Things to Do in Annapolis This Fall
You might have already spent some money on Halloween costumes, autumn décor, and lots of pumpkin-flavored treats. But you don’t have to spend a fortune to celebrate everything that the …
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 Harvest Festival
You won’t want to miss the Annapolis Recreation & Parks Fall Harvest Festival! Sing along with Princesses Elsa, Mirabel, and Tiana, experience the Superhero Training Camp with Batman, Black Panther, …
Family Fall Festival
Join Waugh Chapel Towne Centre on South Main Chapel Way for our annual Family Fall Festival on Saturday, October 24, 2026 from 12:00 pm-2:00 pm! Visit for balloon art, live …
Paws and Pumpkins Fall Fest
Join us for a fun-filled day at the AmericanK9 Dog Ranch in Davidsonville as we celebrate the beauty of fall with our furry friends! The Paws and Pumpkins Fall Fest …
5th Annual Riviera Beach Fall Fest
Get ready for one of Riviera Beach’s favorite community traditions! Join us for an afternoon filled with fall fun, food, live music, games, local vendors, activities for the kids, 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 …
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 …