Annapolis Sailboat Show

October 12th through 15th. Sailors from around the globe gather in beautiful downtown Annapolis every October for the Annapolis Sailboat Show. This annual celebration of sailing features floating docks lined with sailboats from manufacturers around the world. Multihulls, monohulls, cruisers, racers, sailing dinghies and more. Show tents line the shore, stocked with the latest in nautical gear and accessories, electronics, communication equipment, sails, rigging, education, charter companies, clubs and more. Seasoned and novice sailors alike are invited to expand their horizons and connect with fellow sailors during this internationally acclaimed show. Click here for full details.

Annapolis Powerboat Show

October 5th through 8th at Annapolis City Dock. October brings the transformation of Ego Alley and Annapolis Harbor into a boater’s dream, as floating docks create a temporary marina showcasing new and premiering boats and the latest in boating accessories, equipment and apparel during the Annapolis Powerboat Show. Whether you are a boater, angler, or just getting started, you will want to grab your family and head to downtown Annapolis and soak in the boating lifestyle, catch up with old boating friends, and make new ones as you walk the docks. Click here for full details.

Bands in the Sand

Annual fundraising beach concert for Chesapeake Bay Foundation, featuring live music, delicious food and drink, and raffle prizes. Held along the beach of the Philip Merrill Environmental Center in Annapolis. Click here for full details. 

2023 Saltwater Fishing Expo

Presented by the Annapolis Anglers Club. Features dozens of local tackle and fishing vendors, seminars with boat captains and expert anglers, food and beverages (pit beef sandwiches, oysters, etc.), charter captains/guides on site, raffle prizes, and much more.   8 a.m. to 3 p.m. Admission is $5 per person; kids 14 & under are free. Click here for full details.

Walk for the Woods

Walk for the Woods is Scenic Rivers Land Trust's signature community event celebrating the joy of the outdoors and our local, protected woods. This beloved spring event is scheduled for Saturday, April 29, 2023, at Bacon Ridge Natural Area in Crownsville (rain date is April 30). Scenic Rivers will again partner with Anne Arundel County’s Department of Recreation and Parks to offer a wonderful opportunity to hike and explore this beautiful wilderness just minutes from downtown Annapolis. The day features guided hikes, including bird watching, amphibian searches and naturalist hikes, and educational programs. Attendees are also invited to explore the Bacon Ridge Natural Area’s 1000+ acres of woodlands, wetlands, streams, and meadows on their own. It is always a beautiful, relaxing day in our local woods! Click here for full details.

Annapolis Oyster Roast & Sock Burning

Join the Annapolis Maritime Museum for the best Spring party in town! The 11th Annual Annapolis Oyster Roast & Sock Burning has roots that date back the late-1970s, when sailors, shipyard workers, and friends doffed their socks and burned them to celebrate the arrival of Spring! This year's event features live music, plenty of libations, all-you-can-eat oyster, and more fun! Tickets on sale now. Click here for full details and to purchase tickets.

Annapolis Restaurant Week

Seafood lovers rejoice! Annapolis Restaurant Week, presented by the Downtown Annapolis Partnership, will return February 25th to March 5th. This dining event will be hosted at about 40 restaurants in the Annapolis area, including downtown Annapolis, Eastport, Forest Drive, Parole, and surrounding areas. Restaurants are offering special fix price menus during the event featuring  2-course breakfasts, 2-course lunches, and 3-course dinners. A wide variety of cuisines including Italian, Asian, Central American, seafood, steak, and all-American will be offered. Price ranges for breakfast are $9.95 to $15.95, lunch is $12.95 to $19.95,  and dinner is $29.95 to $39.95. Plus, some locations have bonus menu items and specials, which may include 1/2 price bottles of wine, discounted appetizers, or specialty drinks. Participating restaurants, menus, and how to make reservations will be posted at www.annapolisrestaurantweek.com as they are announced by participating restaurants.