It’s 4 pm. You’ve climbed in and out of more cockpits than you can count, your feet hurt, and you’ve got a tote bag full of brochures. Then you walk out the gate, and Ego Alley is right there, full of dinghies and late-afternoon light, with Main Street climbing uphill behind it.
That’s the thing about the Annapolis Boat Shows. The show sits in the middle of one of the best walking towns on the Chesapeake. City Dock is outside the gate, the historic district is a few blocks up the hill, and Eastport is just across Spa Creek.
So you don’t need a separate sightseeing day. An hour before the gates open, dinner afterward, or one free afternoon is plenty. Here’s how our team would spend it.
2026 show dates: Powerboat Show, October 8-11. Sailboat Show, October 15-18. Hours are 10 am to 6:30 pm Thursday through Saturday and 10 am to 5 pm on Sunday.
Before the Show
The gates open at 10. That gives you a couple of hours to see downtown before your day turns into boats, docks, and exhibitor tents.
Getting There
Don’t try to park near City Dock. Park at Navy-Marine Corps Memorial Stadium ($23 prepaid, $30 day of) and take the free shuttle. Or use one of the downtown garages (Park Place, Knighton, Gotts, or Hillman), which connect to the free Magenta Shuttle. One catch: on Saturday, October 10, stadium parking moves to 2644 Riva Road because of a Navy home game.
Grab Coffee
Bitty & Beau’s Coffee is on Dock Street, about as close to the show as coffee gets. It’s staffed by people with intellectual and developmental disabilities, and it’s a genuinely happy place to start the morning.
Rise Up Coffee has a spot right at City Dock if you want a cup to carry along the waterfront. Our marketing team’s order: vanilla cold brew with a splash of cream.
Brown Mustache Coffee is a little farther from the show crowds. Pick it if you’d rather wander downtown for a while before heading in.
Or Sit Down for Breakfast
Chick & Ruth’s Delly on Main Street has been an Annapolis institution for decades. Get there by 8:30 on a weekday (9:30 on weekends), and the whole restaurant stands for the Pledge of Allegiance, a daily tradition.
Iron Rooster is closer to the water and makes its own pop-tarts. We order them every time.
Take the Long Way In
If you have 20 or 30 minutes, skip the direct route to the gate. Walk along Ego Alley, head up Main Street to Church Circle, cut over to State Circle and the Maryland State House, then loop back down to the water.
In half an hour, you go from working harbor to brick streets and 18th-century buildings. Most boat shows don’t come with a view like that on the way in.
Lunch Without Losing Half the Day
After a few hours on the docks, you don’t want a sit-down lunch. You want something good in your hand so you can get back to the boats.
The Big Cheese and Sammy’s Deli on Randall Street is about a three-minute walk from the show. It’s our go-to for grab-and-go sandwiches during show week.
Sofi’s Crepes on Craig Street is steps from the gate and does savory crepes as well as sweet ones. We haven’t tried it ourselves yet, but there’s always a line, and that tells you something during show week.
Show weekends pack a lot of people into a small downtown, and everyone gets hungry at the same time. Grab lunch at 11:30 or after 1:30, and you’ll skip the worst of it.
After the Show: Head to Eastport
When the show closes, cross the Spa Creek Bridge on foot or take the water taxi to Eastport.
It’s five minutes from City Dock, but it feels like leaving the show behind. Downtown has storefronts and show foot traffic. Eastport has marinas, boatyards, and people who actually work on the water.
Dinner spots fill up fast on show weekends. If there’s somewhere you really want to go, reserve it now.
Casual Dinner
Boatyard Bar & Grill is where the boating crowd ends up. The walls are covered in sailing photos of local mariners, and racing footage plays over the bar. Our team loved the Eastport Steamer Sampler.
Davis’ Pub is the neighborhood bar, dark wood and local memorabilia, open since 1986 in what used to be an Eastport general store. Get the crab pretzel.
A Nicer Night Out
Chart House Prime sits right on Spa Creek, looking back across the water at downtown. Book a table for sunset.
Lewnes’ Steakhouse is a classic Eastport steakhouse, the right call if show weekend is doubling as a getaway.
Preserve is the pick if you’d rather stay downtown. It’s on Main Street, and it’s where you go for food you’ll actually remember. We loved the rockfish and the pickled green tomato salad.
End the Night at City Dock
After dinner, walk back across the bridge. The show crowds are gone, Ego Alley is quiet, and Main Street still has enough going on for dessert, a nightcap, or one last lap along the water.
Coming by Boat?
Plenty of show-goers skip the parking question and come by water. If that’s you, the hard part isn’t the show. It’s finding a slip or a spot to anchor on one of the busiest weekends of the year in Annapolis.
That’s where Argo helps. Search for marinas, anchorages, fuel docks, and restaurants near the show, and read reviews from boaters who’ve actually tied up there. Save the ones you like and share them with the rest of your crew, so everyone is working from the same plan.
With Argo Premium, you can build a route to Annapolis around your boat’s draft and height, check the 7-day forecast for wind and waves before you commit to the run, and download charts for offline use in case your signal drops on the Bay.
If You Have a Free Day
Arriving a day early, staying late, or just need a break from the docks? You can see a lot of Annapolis without getting back in the car.
Tour the U.S. Naval Academy
The Academy sits right next to downtown, so it’s the easiest big sight to add to a show trip. Park downtown and walk in through Gate 1. Everyone 18 and over needs a REAL ID-compliant license (look for the star), a U.S. passport, or an enhanced driver’s license. Visitors who aren’t U.S. citizens can only enter with a DoD-credentialed escort. Guided tours leave from the Armel-Leftwich Visitor Center. Rules have changed a few times recently, so check usna.edu before you go.
Take the Historic District Slowly
Start with the same loop from the morning walk, but this time keep going. From State Circle, head down Maryland Avenue and the side streets around it instead of going straight back to the harbor. If you want to make an afternoon of it, the William Paca House and Garden is a couple of blocks away.
See Eastport by Daylight
Eastport is worth more than a dinner stop. Walk past the marinas and boatyards and stop in at the Annapolis Maritime Museum. It’s the best place in town to understand why Annapolis turned out the way it did.
Get Some Space at Quiet Waters Park
After a couple of days of docks and crowds, Quiet Waters Park is a reset: wooded trails and waterfront views, and nobody trying to sell you a boat. It’s a short drive from downtown.
If You Only Have One Afternoon
Have lunch downtown. Walk from City Dock up through the historic district and around the State House. Then cross Spa Creek to Eastport for a walk along the water and dinner.
That’s the harbor, the historic center, and the maritime neighborhood across the creek, all on foot and all in one afternoon. The boats may be why you came to Annapolis. The town around them is why you’ll want to come back.
