2026 Experiences
Discover Annapolis Waterfront Hotel
Spring 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.
More to Explore This Spring
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.