Bay Bridge Boat Show
The local Annapolis boat show calendar sets sail for the first event of the year, the Bay Bridge Boat Show, on April 11-13, 2025. Held on Kent Island – less than a 20-mile drive from downtown Annapolis and reachable by a scenic crossing of the Chesapeake on the 4-mile-long Bay Bridge to Safe Harbor Narrows Point – you’ll find a modern marina and panoramic waterfront views making for a beautiful show location.
The Bay Bridge show focuses on powerboats, with dozens of boatmakers showing off their fleets – ranging from 30-60-foot trawlers, which are versatile and equally suitable for towing nets, liveaboard trips, and long-distance cruising to more fishing-centric and casual boats. Look for legendary trawler brands like Beneteau – celebrating its 140th year in business in 2024 – to smaller upstarts revolutionizing boat design. Pontoons are also hugely popular, as their large decks, flat bottoms, comfortable seating, and easy handling make them ideal for families and social boating, represented at the show by well-known companies like Harris and Bennington.
Every day at Bay Bridge, there are free seminars where you can brush up on your boating knowledge and learn tips from the experts at Boat US, whose apt motto is “Better boating starts here.” Anglers will love the class on light tackle jigging, the best way to catch striped bass in the Chesapeake Bay, and other seminar topics include 10 Skills for Safe Family Boating and Tips for Buying a Used Powerboat – including researching a boat’s history and negotiating with boat brokers.
After a day at the marina, head just a few miles over on Kent Island to Cult Classic Brewing, a favorite of the multiple breweries in Annapolis. Grab a patio table under the springtime sun and enjoy one of their eight specialty pizzas while sipping from 16 award-winning beers on tap, with a brew to suit every palate, from Irish red and amber lager to oatmeal stout and New England IPA.
Annapolis Spring Sailboat Show
Two weeks later, from April 25-27, 2025, the Annapolis Spring Sailboat Show rolls into the center of Annapolis, trading out the motorboats of the Bay Bridge show to celebrate all things sailing. Annapolis holds the unique distinction of hosting the first-ever “in-water” boat show in 1970, a tradition that continues over five decades later and a rare opportunity to step aboard countless sailboats throughout the show weekend. For eight hours on all three show days, hop from boat to boat along the storied slips of Ego Alley – the seagoing thoroughfare of Annapolis City Dock for centuries – while getting a firsthand feel for each sailboat’s idiosyncratic charms and craftsmanship. Insider tip: wear boat shoes, as you’ll have to take off your shoes every time you step on board for a tour.
Among the marina hubbub, you’ll find options for every level of sailboat enthusiast. Beginners can check out entry-level sloops like the Sunfish and Laser, whose simple design, flat hull, and lateen sails are excellent for learning the ins and outs. Larger boats include monohulls, with variations like a center or rear cockpit layout, and more sizable catamarans that provide smooth-cruising stability. And even if you’re not in the market to purchase a high-end boat, take the time to check out one of the top-of-the-line yachts from Tartan or Outbound, whose hand-laid fiberglass hulls, below-board master staterooms, master woodworking, and elegant furnishings will make your jaw drop.
Although the boats are undoubtedly the stars of the show festivities, plan a few hours to stroll through the vendor tents, where companies showcase everything from anchors and modern boat navigation technology to apparel and boat shoes. Chat with reps from smaller boutique brands alongside industry heavyweights like West Marine, who can answer all your niche inquiries about winches, motors, fishing gear, and line rigging.
Tips for an Ideal Annapolis Boat Show Weekend
While you’re in town for the boat shows, take advantage of the opportunity to experience what Annapolis culture and sports offer, filling in your weekend with other fun outings. The sailboat show’s 2025 timing on the last weekend of April coincides with the Ballet Theatre of Maryland’s performance of Swan Lake on 4/25-26. Enjoy this classic of the ballet repertoire in the hallowed confines of Maryland Hall, one of the touchstones of the Annapolis arts scene and also home to the city’s symphony and opera.
For a sportier excursion, attend one of the US Naval Academy home lacrosse games just a mile down the street from us at the Navy-Marine Corps Memorial Stadium. The men’s lacrosse season runs from February through late April, usually with 2 to 3 home games on the schedule throughout April, possibly aligning with one of the boat show weekends (check the USNA sports website for the announcement of the 2025 home schedule).
Between boat show tours at City Dock, visit the moving and educational Kunta Kinte-Alex Haley Memorial, which pays homage to Annapolis’s centuries-old African-American history and heritage. For a quick bite between festivities, grab a sweet or savory treat to-go at Sofi’s Crepes, an Annapolis fave for over two decades, or enjoy a meal overlooking the marina at ChopTank, where the menu includes seafood specialties like Maryland crab dip, Chesapeake rockfish, and decadent lobster rolls. Pussers Caribbean Grille (voted Best City Dock Bar/Restaurant in 2024), also located right on Ego Alley, hosts buzzy boat show happy hours, live music, local DJs, and drink deals (try the “Painkiller” for a tropical cocktail that’ll transport you straight to the islands), a lively atmosphere throughout the weekend.
Stay in luxury and comfort during the spring – when the weather is perfect and the harbor comes alive with Annapolis boat show festivities!