The Montgomery County Business Center, in partnership with M&T Bank, is launching its second free Spanish-language Business Accelerator Program on August 4, offering up to 30 eligible County-based entrepreneurs seven weeks of training in key business development areas, including marketing, finance, and AI tools.
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.
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Actor Jessie T. Usher, widely recognized for his captivating performances as Reggie Franklin/A-Train in Amazon Prime Video’s hit series “The Boys” and as Cam Calloway in Starz’s “Survivor’s Remorse,” is a Montgomery County native.
Earlier this month we let you know that EYA, a Bethesda-based real estate development firm, has closed on the former Rockshire Village Center site in Rockville, marking a key step in its plan to redevelop the long-vacant 7.3-acre property into a mixed-use neighborhood featuring 60 homes, 5,200 square feet of retail space, and community-focused amenities. Now we know that Dunkin’ will be a part of the redevelopment.
Go to New Dunkin’ Will Be Part of Rockshire Village Redevelopment Near Wootton High School
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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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October 10 & 11, 2026
The MoCo Epic is a festival celebrating mountain biking, natural surface trails, and the community that makes this region a great place to ride! 2026 marks the 16th anniversary of the MoCo Epic.
The Montgomery County Police Department (MCPD) responded to a reported stabbing incident in the 19000 block of Germantown Road at 10:21pm Thursday night.
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The Montgomery County Council’s Education and Culture Committee will meet on July 25 to review Montgomery County Public Schools’ Strategic Technology Plan and discuss the implementation of a revised cellphone policy limiting student use of personal devices during the school day. (more…)
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Update: All lanes of US-29 (Colesville Rd) between Fenton St and Spring St have reopened. Expect residual delays.
The Montgomery County Police Department (MCPD) issued a traffic advisory at 7:08 p.m. following an incident involving a pedestrian at the intersection of Spring Street and Colesville Road. The pedestrian, an adult male, was struck and sustained serious injuries. The initial call reporting the incident was received at 6:44 p.m. (more…)
Every September, the charming town of Poolesville bursts into life with the vibrant festivities of Poolesville Day. Scheduled for 10am-4pm on Saturday, September 20, 2025, this event has been a cornerstone of community celebration for more than 25 years. Held at Whalen Commons, Poolesville Day is a free, one-day extravaganza that attracts over 12,000 visitors eager to soak up the spirit of Poolesville.
We tried the legendary $140 cheesesteak at Barclay Prime in Philadelphia and we’ll tell you all about it as we answer the question everyone asks… “was it worth it?” (video below).
Detectives from the Montgomery County Department of Police – Special Victims Investigations Division are continuing to search for Nehemie Price, a missing 14-year-old, and are asking for the public’s assistance in locating her. (more…)