Annapolis knows how to mark a season. From late September to early December, 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 Annapolis Waterfront Hotel.

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.

Art @ the Park

October 11–12, 2025

Tucked between trees and water, Quiet Waters Park is aptly named. During Art @ the Park, 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.

Maryland Avenue Fall Festival

October 19, 2025 

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 2–5 & 9-12, 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.

Bay Bridge Run 

November 9, 2025 

Once a year, the Chesapeake Bay Bridge opens to foot traffic. Some jog, others walk. Either way, it’s a rare and exhilarating chance to cross one of Maryland’s most iconic spans without a single engine in earshot. The views? Expansive. The mood? Light. A perfect way to see the Bay in motion.

Chocolate Binge Festival

December 7, 2025 

Few festivals name themselves so honestly. This downtown event is equal parts indulgent and whimsical: local chocolate vendors, fire pits, and live music tucked between twinkling lights and holiday cheer. There’s a sense of familiarity here, even for first-timers. It’s less about the sugar (though there’s no shortage of that), more about the spirit.

Midnight Madness 

December 4, 11, & 18, 2025

Each Thursday in December, the shops of Main Street and Maryland Avenue keep their lights on late. There’s music, mulled drinks, and a gentle buzz in the air. Despite the name, it’s not chaotic, it’s convivial. Friends run into neighbors, visitors are welcomed like regulars, and for a few hours, the streets feel lit from more than just the overhead lights.

Eastport Yacht Club Lights Parade 

December 13, 2025

Sailboats wrapped in lights drift across the harbor. It’s as simple and magical as that. Some go big with themes and music, others keep it classic. From the dock or your harbor-facing room, it’s Annapolis at its most quietly dazzling. 

Before You Head Out

Fall in Annapolis comes with a few quiet truths: the air cools faster by the water, the brick and cobblestone streets tell the stories, and some of the best moments aren’t on any itinerary. Bring layers, wear shoes you trust, and leave space in your plans for the unplanned—a second cider, a detour through Eastport, a boat parade that holds your gaze longer than expected. 

And when the night winds down, the harbor’s still waiting. From your room at Annapolis Waterfront Hotel, you’re never far from a good meal or a well-poured drink. Plush bedding, MALIN+GOETZ amenities, and a view that doesn’t ask for anything, just time to take it in.

A Season Well-Spent

Autumn and early winter suit Annapolis: brisk, blue-skied, and quietly magnetic. Whether it’s light-strung sailboats or a well-thrown pottery mug, the city’s charm is in the details. The festivals aren’t filler, they’re expressions. And each one is a reason to stay a little longer, breathe a little deeper, and take something meaningful with you when you leave.