George Washington, Benjamin Franklin and Thomas Jefferson walk into a bar … No, it’s not the beginning of a joke. These three Founding Fathers actually hung out in Annapolis, Maryland, on occasion. They were known to stop in for a pint at Middleton Tavern by the harbor, where you can still order a mug of suds and slurp some oysters, with rickety floors underfoot.
The capital of Maryland, Annapolis was the first peacetime capital of the United States between 1783 and ’84. Today it’s a city with a culture dominated not just by history, but also by a robust boating scene. A sign on a city road once read, “America’s Sailing Capital.” The sign was eventually moved to a saltier section of town, where it was better appreciated, and sailors and powerboaters alike still flock to Annapolis to experience the scenic waters, eat and drink at the restaurants and bars, and soak in the maritime vibe.
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The approach to Annapolis is friendly and well-marked. Back Creek will come into sight first, to port. Once you’ve rounded the Horn Point shoal marker, Annapolis Harbor and Spa Creek slowly reveal themselves. You’ll find city-maintained moorings in the main harbor and farther up Spa Creek beyond the Eastport Bridge for $35 a night. The harbormaster comes by daily to collect the fee, and a pumpout boat makes daily rounds.
Anchoring is allowed in some open areas, especially farther up the creek near Truxtun Park. Farther from downtown, Back Creek is also peppered with city-run moorings for $35 a night, and it has more space for anchoring.
A water taxi network runs around both creeks to prominent spots ashore. You can hail a ride on VHF channel 68 or by dialing (410) 263-0033. Fares run between $3 and $8, depending on distance.
Virtually every inch of shoreline on both Spa and Back creeks is dedicated to marinas and marine service facilities, so finding a place to tie up is generally easy. However, on weekends, especially holiday weekends, reservations are essential.
If you really want to be part of the action, the city maintains bulkhead and slip spaces on Ego Alley, smack in the middle of downtown. The rectangle-shaped sliver of water is named for the stream of boats that parade up and down as people ashore gawk at the procession of fiberglass and horsepower.
Fuel is available at two fuel docks on Annapolis Harbor proper — Annapolis Yacht Basin and Annapolis City Marina. Back Creek’s Annapolis Landing Marina also serves up gas and diesel.
Annapolis’ waterfront scene can primarily be divided into two areas. Downtown Annapolis is on the north side of Spa Creek and is filled with historic homes, brick-clad streets and sidewalks, and more shops and restaurants than a person can visit in a day. The U.S. Naval Academy is worth a stop; John Paul Jones is interred beneath the Academy Chapel. Leave your bicycles on the boat, and bring a valid photo ID.
The Maryland State House and other historic properties, such as the William Paca House (186 Prince George St.) and Charles Carroll House (107 Duke of Gloucester St.) are also interesting. With lots to see and take in, simply walking around is a pleasure.
When you get hungry, most eateries are within walking distance. Joss Café & Sushi Bar (195 Main St.) has premium sushi. Fox’s Den (179B Main St.) is a newcomer to the scene, serving a gastropub menu with an excellent selection of craft beers. Chick & Ruth’s Delly (165 Main St.) is a beloved institution that has a varied menu, and locals recommend it for breakfast. The Iron Rooster (12 Market Space) also gets rave breakfast and brunch reviews.
Lots of visitors want to sit down and pick steamed blue crabs — a quintessentially Maryland thing to do. If you want the real deal, grab an Uber or Lyft and head to Cantler’s Riverside Inn (458 Forest Beach Road). You might have to wait for a seat, but you’ll be rewarded with lots of fat steamed crabs piled high on craft paper. They’re caught primarily by the owners from local waters.
Eastport is downtown Annapolis’ rebellious neighbor across Spa Creek, populated by salty folks with a love for the water and a penchant for mischievous civil protest. When the drawbridge joining the two communities across Spa Creek closed for repairs in 1998, Eastport residents seceded, forming their own faux government, air force and navy. They even gave Eastport a new name: The Maritime Republic of Eastport. The peninsula the neighborhood lies on is loaded with marinas, boatyards, restaurants and other maritime-oriented businesses.
Hungry or thirsty folks looking to tune in to the local boating scene will want to visit Davis’ Pub (400 Chester Ave.) or Boatyard Bar & Grill (400 Fourth St.). Davis’ is an authentic neighborhood pub with good grub, excellent service and well-poured drinks — a local favorite. Boatyard Bar & Grill is on the north side of the Eastport peninsula and serves all sorts of dishes, including seafood and steaks. You’ll want to take advantage of its raw bar and throw back some local oysters.
Fancier seafood dining is at Chart House (300 Second St.), Carrol’s Creek Café (410 Severn Ave.), and O’Learys Seafood (310 Third St.). Carrol’s Creek Café and Chart House have amazing views of the harbor. On Wednesday evenings, the Annapolis Yacht Club’s weekly summer sailing races finish at the Eastport Bridge, the boats gliding right by your table.
Once you’ve done all the “must do” items on your list, lounge about the boat and enjoy the rhythm of the city. Annapolis is an amazing place that has something for everyone.
This article originally appeared in the June 2017 issue.