Marylanders urged to check exposure times, monitor symptoms, and make sure vaccinations are up to date
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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.
The Metro Board of Directors is seeking applicants to serve on its Riders’ Advisory Council (RAC) to provide input on service, policies and other initiatives that assists Metro’s Board of Directors in its decision-making.
A vehicle fire that occurred after a collision has stopped traffic on southbound I-270 near exit 6 on Saturday night.
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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BETHESDA, YOUR SATURDAY MORNING PLANS JUST GOT MORE CREATIVE.
Join Craft Cart at Coffee Republic on Saturday, September 26, from 11:00 AM–1:00 PM for a beginner-friendly faux stained glass experience filled with creativity, coffee and connection.
The Montgomery County Council will review state and local legislation, economic development indicators, and capital projects during upcoming meetings. Committees will discuss budget updates, public safety appropriations, the Bethesda Downtown Plan Minor Master Plan Amendment, and proposed changes to animal control laws. Full agenda below courtesy Montgomery County government:
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We have recently received inquiries about the canceled appearance by Henry Winkler at Montgomery College’s Robert E. Parilla Performing Arts Center, located at 51 Mannakee St., Rockville. We would like to remind everyone that this event was canceled last month. Originally scheduled for October 29, 2024, the event was later rescheduled to March 11, 2025, before being canceled indefinitely.
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The Montgomery County Police Department (MCPD) is investigating a homicide in the 2700 block of Fairdale Terrace in Silver Spring. (more…)
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Last week, we reported that the National Park Service (NPS) has predicted peak bloom for the DC area Cherry Blossoms to fall this year (2025) between March 28-31. If you’re […]
Benjamin Banneker Middle School in Burtonsville is buzzing with accomplishments and exciting programs, showcasing the school’s commitment to excellence in both academics and extracurricular activities. The PTSA shared the following news with us:
Montgomery County received positive ratings in the 2024 National Community Survey, with 84 percent of respondents describing it as an excellent or good place to live.