Roadside America: Annapolis

An Annapolis native rolls their eyes when dining out of state and they’re informed that a restaurant has “really good crab cakes.” They can tell the season by the color of a midshipman’s (Naval Academy student) uniform, and inform you that a “Johnny” is not a young boy but a student at the town’s other university, St. John’s.

So who better to tell you about this scenic state capital than a local? We can’t think of anyone either. Here’s the down and dirty on our hometown.

An easy day-trip drive from cities like Washington, D.C., and Baltimore, and an equally simple overnight for those from as far away as Philadelphia and Richmond, the lure of this historic town is simple: water, water everywhere.

Want to visit Annapolis? Here’s what you need to know.

Play Tourist:

Start your trip downtown at the docks. Dubbed “Ego Alley,” the main city dock has dozens of large boats that pull up each day. It’s fun for spectating, and there’s plenty of seating for those who want to enjoy a cold beverage or ice cream cone. You can also catch a $13 waterfront cruise from City Dock, a great way to see the town by water.

Next, walk up Main Street, popping in and out of boutiques as you like – you’ll find a lot of souvenir shops but also some clothing stores, galleries and even national vendors like Sperry and Helly Hansen. When you reach the top of the street, head to the right, around Church Circle, and continue on to State Circle. You can then take a walk down Maryland Avenue, which is heavy on the design boutiques and art galleries. From here, you can reach one of the minor gates of the United States Naval Academy. During daylight hours, you can walk on to the campus by showing your ID. You can stroll the grounds, visit the chapel and stop by the Visitors center, which offers a number of free exhibits. Guided tours are available until 3 p.m. and are $9.50 for adults.
When you stroll out the front gates again, you’ll pretty much be right back where you started – and it’s time for a cocktail!

If you’re visiting during the late spring, summer, or early fall, you absolutely must experience crabs. Make the drive to Cantler’s if you’re in search of the steamed or soft shell variety. If you’d prefer a great crab cake, try O’Learys instead.

If you’re visiting on a day trip and are enjoying just a meal and a snack, we’d prefer to satisfy our cravings while on-the-go with a quick pit stop at Annapolis Ice Cream Company, which churns out the town’s best homemade treats in flavors like Mint Oreo and Apple Pie. If you’d rather sip your calories, the famed Chick & Ruth’s Delly features a 6-pound shake on the menu (yes, you may have seen it during an episode of “Man vs. Food”).

If you’re staying overnight, you’ll find that most bars along Main and West Streets cater to a casual crowd. Feel free to come in fresh from an afternoon on the boat and order a brew at McGarvey’s (where the Navy’s Blue Angels hang out when they’re in town) or the 250-year-old Middleton Tavern (order some oysters with your cocktail). Or, head to West Street and try the local brews at Rams Head Tavern, where you can frequently catch local and national musicians playing for the evening. For a true scenic dining experience, head across the water to the Severn Inn, which offers panoramic views of the bay and downtown.

For brunch, lovers of the casual will find a locals hangout at Boatyard Bar & Grill, just across the bridge in Eastport.

Tips for Day-Trippers:

  • Plan to do some walking. Finding a parking space downtown on weekends can be tough, so you’ll want to leave it in a public garage (there’s one on Main Street) or at your hotel if you can. Downtown is pretty walk-able, but you’ll want flat, comfortable shoes for the brick sidewalks.
  • Preppy chic is the dress code of choice for most Annapolis natives – most restaurants won’t require more than a collared shirt for dinner, although a blazer wouldn’t look out of place either.

[Flickr image via jeffweese]