Experience
Discover Annapolis Waterfront Hotel
Annapolis knows how to mark a season. From late summer to early fall, the city fills its calendar with festivals that feel both local and lasting-anchored in crisp weather, coastal views, and a pace that invites you to stay a while. From cobblestone street fairs to boats lit for the holidays, these are the festivals that give the season its character-all within reach of
Rotary Club of Annapolis Crab Fest
August 1, 2025
Held rain or shine since 1946, the Annual Rotary Crab Feast is one of the longest-running and most popular summertime traditions in Annapolis! Known as “the world's largest crab feast,” the all-you-can-eat (and drink) event invites folks from near and far to get their fill of Maryland's famous blue crabs plus Maryland vegetable crab soup, sweet Maryland corn on the cob, beef barbeque sandwiches, all-American hot dogs, watermelon, draft beer, and assorted sodas and wate
Maryland Renaissance Festival
August 23 - October 19, 2025
Just outside town, a wooded path leads to a different century. The Renaissance Festival is theatrical, sure-but it's also a craft fair, an open-air tavern, and a stage for improvisation. Come for the spectacle, stay for the storytelling, and leave with treasures as memorable as the day itself.
Autumn On The Farms
Late September Through October
Just outside Annapolis, the farmland opens up-and so do the gates. Knightongale Farm and Greenstreet Gardens keep to the fall essentials: corn mazes, hayrides, apple cannons, and rows of pumpkins waiting to be picked. Homestead Gardens brings a different kind of charm, blending nostalgic traditions with thoughtful touches-barnyard animals, community hayrides, and spaces designed for making memories. Each farm offers its own take on the season, but all share the same spirit-a chance to slow down and take the season in, one hay bale at a time.
Fall Crafts Festival at Quiet Waters Park
October 11 - 12
Tucked between trees and water, Quiet Waters Park is aptly named. During the Crafts Festival, its winding paths are lined with artists selling hand-thrown ceramics, ironwork, textiles, and photography. It's a reminder that beauty can be practical-and that taking your time is often the point.
Learn MoreMaryland Avenue Fall Festival
October 19
This neighborhood festival lives in the details: soft jazz from a front porch, antique finds beside handmade leather goods, fresh cider clutched in gloves. It's a small-scale festival with a big sense of place-charming, personal, and unmistakably Annapolis.
Annapolis Boat Shows
October 2 - 12, 2025
For ten days, the city's maritime legacy takes center stage. The Annapolis Powerboat Show and Annapolis Sailboat Show bookend the stretch, as sail and power converge on the harbor and floating docks host boats from all over the world-sleek catamarans, polished teakwood cruisers, and everything in between. It's a show of craftsmanship, culture, and connection-one that draws mariners, dreamers, and curious newcomers alike.