Governor Wes Moore issued the following statement on Saturday, June 14: (more…)
The sailing lifestyle starts with a single moment. A breeze filling the sails. A quiet morning on the Bay. A weekend exploring new places with nothing but the horizon ahead.
For generations, the Chesapeake Bay has inspired sailors with its protected waters, charming waterfront towns, and endless opportunities to explore. It’s a place where a short afternoon sail can become a lifelong passion, and where every trip on the water offers a new adventure.
Every fall, the Annapolis Sailboat Show brings that lifestyle within reach.
From October 15–18, downtown Annapolis transforms into a celebration of sailing, bringing together beautiful sailboats, passionate sailors, industry experts, and waterfront experiences in America’s sailing capital.
Walk the docks, step aboard sailboats from around the world, discover new designs, connect with the sailing community, and imagine where the wind could take you next. You don’t have to be an experienced sailor to enjoy the show. You just have to be curious.
Discover Your Place Under Sail
The Annapolis Sailboat Show offers a rare opportunity to experience the sailing world all in one place. Explore sleek performance sailboats built for adventure. Step aboard comfortable cruising yachts designed for weekend escapes. Discover spacious catamarans that offer a new way to experience life on the water.
Every boat represents a different possibility.
Maybe it’s learning to sail for the first time. Maybe it’s planning weekend adventures on the Chesapeake. Maybe it’s simply discovering a new passion you never knew you had. Walk the docks, talk with sailing experts, and explore the boats, brands, and resources that can help make sailing part of your story.
More Than a Sailboat Show
The Annapolis Sailboat Show is more than an event. It’s a celebration of the people, places, and experiences that make sailing special.
Beyond the docks, visitors can experience the best of fall in Annapolis. Stroll historic brick-lined streets, enjoy waterfront dining, browse local shops, and take in views of sailboats moving through the harbor.
Throughout the show grounds, connect with sailing organizations, charter companies, outfitters, and marine experts who help make the sailing lifestyle more accessible. It’s a weekend filled with discovery, community, and the unmistakable energy of a city built around the water.
Learn. Build Confidence. Go Farther.
For many people, sailing is a dream they’ve always wanted to explore but didn’t know where to begin. The Annapolis Sailboat Show helps turn curiosity into confidence.
Take part in educational opportunities designed for every level of experience, including the First Sail Workshop for beginners, Cruisers University for in-depth sailing education, and free daily seminars led by experienced sailors and industry experts.
Whether you’re stepping aboard for the first time or building the skills to go farther, these programs provide the knowledge and confidence to enjoy more time on the water.
Find Your Next Adventure
Sailing is about more than the boat.
It’s the quiet morning sail. The sunset over the harbor. The weekend escape with friends. The feeling of discovering somewhere new. The Annapolis Sailboat Show brings together the boats, people, and possibilities that make the sailing lifestyle so rewarding.
Come step aboard, meet the sailing community, and discover where your next adventure begins.
MCPS has announced that Douglas Rivera is this year’s High School Counselor of the Year. According to MCPS, Rivera is entering his 10th year as a school counselor at MCPS, where he continually exemplifies commitment and passion for student success.
On Friday, Governor Wes Moore released the following statement ahead of planned protests across the State of Maryland: (more…)
We’ve Got the Ticket to Every Sunday Showdown! 🏈🔥
Catch every live out-of-market Sunday game with NFL Sunday Ticket this football season at Lucky Strike Rockville!
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Come enjoy the day at our annual Washington Grove Arts and Craft Festival in a beautiful outdoor setting. This festival highlights local artisans including wood creations, pottery, visual art, household products and so much more. We also have food trucks from El Parente Tacos, El Jeffe Wood-fired pizzas, Bruster’s Ice Cream and beverages from Saints Row Brewery. Bring the whole family because we have a kids activity area too. Pets on a leash are welcome too!
On Saturday, June 14, 2025, Montgomery County Executive and County Council released a statement condemning the politically motivated shootings in Minnesota, expressing solidarity with the victims and calling for the rejection of political violence.
Maryland Attorney General Anthony G. Brown joined a bipartisan coalition of 51 attorneys general in supporting a veteran’s legal challenge to ensure full G.I. Bill education benefits and the ability to transfer them to family members, in line with a recent U.S. Supreme Court ruling.
The 26th annual Heritage Days festival will take place June 28–29 from noon to 4 p.m., offering free access to historic and cultural sites across Montgomery County with exhibits, tours, live music, and family activities.
On Friday, Maryland officials and stakeholders convened for a roundtable to address the potential impacts of over $1 trillion in proposed federal budget cuts, which could significantly reduce Medicaid, health insurance, and SNAP benefits for hundreds of thousands of Marylanders.
Silver Diner has just opened its new 1,581 square-foot pergola for outdoor dining at Silver Diner RIO (9811 Washingtonian Blvd in Gaithersburg). The structure now features a louvered roof and walls equipped with a retracting window and roof system.
Pura Vida Miami, which has emerged as a prominent wellness-driven café chain, is planning to open its first Maryland location. According to The Burn, Pura Vida will be opening its first DC-area location in Fairfax, VA, with its first Maryland location coning to Potomac’s Cabin John Village shopping center.
Lindzy Davis has been named the MCPS Elementary School Counselor of the Year. According to MCPS, Davis began her career in Baltimore City, where she discovered a passion for building relationships with students and removing obstacles to their success. After joining MCPS in 2018 at Earle B. Wood Middle School as a long-term substitute, she secured a permanent role at Georgian Forest Elementary School before arriving at Flower Hill in 2022.