2026 Experiences
Discover Annapolis Waterfront Hotel
Winter in Annapolis is anything but still. Between full tables, full sails, and a full lineup, you’ll find a city that doesn’t hibernate, but layers up and leans in. Here’s what’s stirring in and around the harbor.
Frostbite Series at Annapolis Yacht Club
Sundays, February 3–March 17
Even in winter, the waters of Spa Creek stay restless. Each Sunday, the Frostbite Series launches a fleet of sailboats into brisk wind and open sky. Hosted by the Annapolis Yacht Club, this long-standing tradition draws seasoned sailors and curious onlookers alike. Watch from the docks, your balcony, or the edge of a harborside stroll. It’s an only-in-Annapolis winter scene, sails and all.
Valentine’s Weekend in Annapolis
February 14–15
Love takes many forms in Annapolis, and this Valentine’s weekend, it’s everywhere. Hear 17th-century poetry and song at Hammond-Harwood House, or settle in for a romantic Candlelight string concert at Maryland Hall. Jazz-pop artist Emmaline brings her celebrated Be My Valentine tour to Rams Head, while the hotel’s Love on the Harbor package offers sparkling wine, breakfast for two, and a room in the heart of it all.
Annapolis Restaurant Week
February 21–March 1
Annapolis plates its best this week, as more than 30 restaurants offer multi-course meals at fixed prices. Historic dining rooms hum with conversation, new kitchens open their doors, and takeout bags carry the same care as a table for two. It’s a week to eat slowly, try boldly, and taste the city one dish at a time.
St. Patrick’s Day Celebrations
March 7–8
Green scarves whip in the wind, drumlines echo down brick roads, and pint glasses clink from street to street. The festivities begin Saturday with the Hooley, a lively kickoff gathering of Irish fare, open-bar toasts, and traditional music at the Naval Academy Alumni Center. By Sunday, the city turns out for the St. Patrick’s Parade. Pipes echo through historic streets, flags ripple over the crowd, and storefronts spill out with revelers. In a town lauded for its traditions, this one knows how to make some noise.
Maryland Day Celebrations
March 19–25
Annapolis and the surrounding Chesapeake Crossroads region mark Maryland’s founding with a week of open doors and open archives. Tour colonial schoolhouses and centuries-old streets, trace foodways at the Chesapeake Children’s Museum, or follow murals that tell stories in color. With more than 50 sites across Anne Arundel County, the celebration blends past and present into something tactile, layered, and uniquely local.
Annapolis Film Festival
March 26–29
For four days in March, downtown theaters, galleries, and tucked-away venues screen more than 70 international features, debuts, and local documentaries. Theaters glow into the night; post-screening conversations spill into cafés; filmmakers gather for panels; and off-script encounters turn cinephiles into fast friends. Walkable, watchable, and alive with dialogue, the festival fills Annapolis full of stories that echo long after the screens go dark.
More to Explore This Winter
Temperatures may drop, but Annapolis’s calendar stays full. At Honey’s Harvest Farm, the First Sunday Farmers Market gathers bakers, brewers, and artisans under the beams of a heated barn, music drifting through the cold. Inside Maryland Hall, the Naptown Flea Vintage & Vinyl Market offers retro finds and local DJ sets that pulse with nostalgia. And on select Thursday evenings, Dodon Vineyards hosts Yoga in the Vineyard, a slow-flow class followed by wine and candlelit conversation. It’s the kind of winter you only find here, in beautiful Annapolis, Maryland.
Annapolis Spring Sailboat Show
April 24-26
Since 1970, the Annapolis Boat Shows have drawn sailors from around the world to the Chesapeake Bay. Each spring, the Annapolis City Dock hosts three lively days of in-water discovery, where catamarans, monohulls, racing boats, and inflatables fill the harbor. With more than 100 new and brokerage yachts on display, plus the latest gear, electronics, and apparel, the Spring Sailboat Show offers an easy, immersive way to explore what’s new in sailing.
Let's Go! Music Festival
June 5-6
The Let’s Go! Music Festival is the ultimate summer kickoff, a two-day celebration of live music, local flavors, and good vibes in Crownsville, Maryland. Held at the Anne Arundel County Fairgrounds, this fan-driven festival brings together an exciting mix of top artists, emerging bands, and regional talent. Pair that with fantastic food, refreshing drinks, and an unbeatable festival atmosphere, and you’ve got the perfect way to start your summer.
Annapolis 250
July 4
This July 4th, the United States will celebrate its 250th anniversary. Celebrate this historic milestone with a wide array of events honoring our nation’s diversity, strength, and the key role of Annapolis and Anne Arundel County in its founding.