With so many sailors in America’s Sailing Capital at Sailboat Show time, here is an updated 2025 refresher course on all things Annapolis, with locals’ tips on things to do and where to go, places to learn about Annapolis' unique history, and some historical tidbits about Maryland’s capital that may surprise you.
Five things local sailors know about Annapolis:
To get you into the locals’ frame of mind, here are five things Annapolis sailors know:
- Where to find a great crabcake. First stop, the Boatyard Bar & Grill in Eastport, where the crabcakes win awards and are so popular, they send them all over the country. If you’re in the mood for an adventure (but you’ll need to drive), go to Jimmy Cantler’s Riverside Inn, but go early, as there could be a line.
- Where to see the best sunset. Sailors see the best sunsets from the water sailing toward Annapolis. If you’re in town for the Sailboat Show and don’t have boat access, we recommend the Schooner Woodwind for a two-hour sunset sail—or an hour-and-a-half-long one departing from the show (see schoonerwoodwind.com or find the crew on Dock F2 inside the show). The next best place to see the Annapolis sunset is from the Eastport Bridge at 6:33 p.m. The other place depends upon your luck in snagging a spot on the Main-Street-facing upper deck of the Choptank Restaurant. Good luck!
- Where to relax. Besides restaurants, bars, and coffee shops, where do you go outside the boat show gates to take in the scenery? On almost every street end in the Eastport section of Annapolis, you will find a pocket park with a bench and a view. If you enter the Naval Academy, you may find benches along the seawall and in several pretty spots on campus (bring your REAL ID; you must pass through a metal detector). If you’d like to take a stroll in the woods, there’s a wonderful, four-mile paved trail at Quiet Waters Park and a gazebo overlooking the South River (3.4 miles from the show).
- Where to find a table. It’s boat show time, which means packed restaurants on City Dock and Main Street—and you’re getting hungry, aren’t you? You don’t have to walk far to find something, just far enough away from the show hub. We locals like Galway Bay Irish Pub on Maryland Avenue. Another idea would be to walk up West Street and try Reynold’s Tavern, Ram’s Head Tavern, Tsunami (for sushi), or Picante (for Mexican); walk just a bit farther and you will find Sailor’s Oyster Bar, Metropolitan Kitchen, and Lemongrass (Thai). Your other option would be to continue reading this article until you see the title “Fourth Street Shuffle.”
- Where to find the best events. If you’re in town for the Annapolis Sailboat Show, you’ve already found our best event, but wait, there are more! Annapolis specializes in quirky events, so come back for the Tug o’ War (aka the Slaughter Across the Water), where teams from Eastport and Annapolis battle with the longest tug-of-war rope in the world across the Annapolis Harbor for bragging rights. It’s a party not to be missed (November 8 at the crack o’ noon) and raises funds for local charities. Other SpinSheet favorites include the Annapolis Maritime Museum Oyster Roast and Sock Burning (in March), Bands in the Sand (in June), and the Boatyard Beach Bash (in September). We print as many fun events as we can fit in the SpinSheet Calendar.
Two new restaurants on the scene
At long last, the Rumhouse, a Caribbean restaurant on Sixth Street, is open (go straight across the Eastport Bridge and walk two and a half blocks). Our publisher gives it her seal of approval for interesting cocktails, great food, and a tip-included bill (no stress!). Find the menu and make a reservation at rumhouseannapolis.com.
It may seem far away after a long boat show day, but it’s only a one-mile walk (or short shuttle ride) to SeaSalt Annapolis next to the Westin on West Street. SeaSalt sources fresh, seasonal, and sustainable fish, shellfish, meats, and produces craft cocktails. They offer an “Anchovy Hour” Monday through Friday from 3:30-6 p.m.
Guided or self-led history tours
The first thing you should know about visiting the US Naval Academy (USNA) or the Maryland State House is that they’re both open to the public, yet you will need to present a photo ID and pass through a metal detector to enter. If that’s okay, read on!
To see the USNA campus or “the Yard,” enter the Armel-Leftwich Visitor Center to watch the 13-minute film, “The Call to Serve,” which repeats every 15 minutes. The exhibit area is a mini-museum with several interactive screens, including maps and guidance to help you orient yourself on the Yard. There are several kiosks with interactive videos featuring midshipmen and recent graduates who discuss admissions, academics, student life, and career options. Be sure to check out the USNA gift shop and the museum.
If you would like to take an historical tour, USNA provides a number of guided tour options. When you’re exploring the Yard, you give back in a meaningful way, since 100 percent of the profits from tours, merchandise, and meals purchased go to support the Brigade of Midshipmen. The Visitor Center is open daily from 9 a.m. to 5 p.m. as is the USNA Gift Shop. Learn more and buy tickets at navalacademytourism.com/visitor-center.
The Maryland State House, the oldest state capitol (1779) still in legislative use, is open to the public every day from 8:30 a.m. to 5 p.m., except Christmas and New Years Day. To help make your visit more enjoyable and to provide you with an understanding of its rich and historic past, self-guided tour information is available on the first floor. You may also download a free visitor’s guide at msa.maryland.gov/msa/mdstatehouse/html/visitor.html.
The Fourth Street shuffle
As locals, SpinSheet staffers frequent several restaurants and watering holes, almost all of them in Eastport! It’s not unusual to find one or more of our staff along Fourth Street at lunchtime, happy hour, or dinnertime any night of the week. First stop: the Boatyard Bar and Grill. With an extensive menu, daily specials, a raw bar, consistently good food, award-winning crabcakes, pint-sized drinks, and coloring for kids, this restaurant is a must for any Annapolis visitor, especially one who loves sailing and fishing and will appreciate the Key West attitude and memorabilia on the walls.
Down Fourth Street a few doors, you will find Forward Brewing. Family-friendly, dog-friendly, and owned by local sailors, Forward brews craft beers and offers a creative, delicious menu. One door down, you’ll find Adam’s on Fourth, a new take on the more traditional Adam’s Ribs’ fare, offering craft beer and cocktails and good food.
Once you’re on Fourth Street, you might as well keep going to the “most local of local sailor’s bars” in town: Davis’ Pub, which faces Back Creek; the picnic tables outside are the best. You may tell yourself you don’t need the crab pretzel and all that cheese, but we beg to differ. Always get the crab pretzel.
SpinSheet staffers have three other favorite lunch spots: Bread and Butter Kitchen (on Second Street facing Annapolis) for the BBK breakfast sandwich, the Leeward Market (Second Street, on your way to AMM) for pizza and sandwiches, and the Eastport Kitchen for everything on the menu. This last one is at the Eastport Shopping Center (a long walk), but if you’re traveling out of town by car or bike, it’s worth your while. Not only are the owners sailors, but the food is also delicious, the service is exceptional, and they open for dinner Thursday through Saturday.
Don't get lost at sea! (See some art for free!)
If you’d like to see some interesting art, visit the Mitchell Gallery on the St. John’s College Campus, which is only a 10-minute walk from the boat show gates. The exhibit, “Lost at Sea (Ulysses),” is a story of adventure, courage, tragedy, and unspeakable loss. It is a grappling for direction and meaning, a yearning for communication and connection, amidst the erosion of both language and logic. But most of all, it is the story of humans face to face with the great unknown. The free exhibit features sculpture, painting, and prints by nine artists from North America and Europe and is open Thursdays, Saturdays, and Sundays 10 a.m.–6 p.m. and Fridays from 2–7:30 p.m. Learn more at sjc.edu/mitchell.
A Little Bit of History: When Annapolis Wasn't So Cool, Calm, and Conservative
We celebrate Annapolis today as a sailing Mecca, a genteel tourist town welcoming tourists and sailors and cruisers from around the world. But in August 1765, Annapolis exploded when a mob of 300 angry protesters, led by Samuel Chase (future signer of the “Declaration of Independence”), marched to City Dock where Zachariah Hood’s ship had just arrived. While on business in London, Hood had accepted a royal Stamp Act commission, thinking it was a good idea to collect taxes from family, friends, and neighbors. Oops.
In one version of events, the mob dragged a wagon with gallows and effigy to the dock, set it afire, and let it fall into a crude coffin to welcome Hood home.
In other reports, the mob paraded through the city with the wagon/effigy ahead of Hood’s arrival. A few days later, the mob re-assembled at the harbor where a scuffle broke out when Hood disembarked.
In either case, Hood was chased out of town, never allowed to return, and the mob later ransacked his business office. He escaped to New York, only to be hounded again by the Sons of Liberty, who forced Hood to resign his commission. Things never worked out well for Hood after this crisis.
The cause of all this unrest: the colonists insisted they had the legal right to be represented in tax decisions. Colonials had offered to raise their own revenues to pay off the huge cost of the French and Indian War. However, King George III and Parliament made it clear they were not going to share power and give colonists a say in lawmaking. Members of Parliament believed that only they were “born to rule.” American colonists were second-class subjects, “born to-be-ruled,” and should obey like dutiful children. Result: Unrest, protests, war, and England losing her 13 colonies.
Note: The Stamp Act provides the backdrop for Thomas Guay’s historical novel, “Chesapeake Bound,” published this year by McBooks Press. Learn more at thomasguay.com.
