Annapolis: A day trip

Here on the East Coast, the weather has warmed, reached scorching, and cooled again. The nights are long, the fireflies abundant, and the waterfront beckons. And it’s this same time of year that this Annapolis native (or Annapolitan, as we are often called) is besieged with e-mail and phone messages asking about what one should do in our beloved hometown on a weekend trip.

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:


If you’ll want to spend the majority of your time near the water or within walking distance to most of your activities, you’ll need to reserve a hotel or inn downtown. Consider the Annapolis Marriott for the best water views. The hotel restaurant, Pussers, is also a popular evening spot – order the signature Painkiller cocktail, a deadly yet delicious blend of juices and rum.

On West Street, the new-ish Westin hotel is slightly less expensive and features spacious rooms and a complimentary shuttle to Main Street. It’s about a 15-minute walk downtown, and you’ll pass numerous restaurants, bars and shops along the way.

Should you care for something a bit more boutique, try the Historic Inns of Annapolis collection – three hotels (The Maryland Inn, Governor Calvert House, Robert Johnson House) that feature a more bed and breakfast-style approach and, in some cases, a history that dates back to the 1700s.


No trip to this seafood-laden city is complete without a crab picking. Make the drive to Cantler’s if you’re in search of the steamed or soft shell variety. If you’d prefer a great crabcake, try O’Learys instead.

While you’re strolling the boutiques of Main Street, don’t miss a stop at Annapolis Ice Cream company. Their homemade ice cream comes in flavors like Mint Oreo and Apple Pie. Are milkshakes more your speed? The famed Chick & Ruth’s Delly features a six-pound shake on the menu (yes, you may have seen it during an episode of Man vs. Food).

Want a trendy night out spot? Sample the small plates, many featuring locally-sourced ingredients, at Level, or the upscale Italian at Osteria 177.

When it comes time to hit the town, 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), the 250 year old The Middleton Tavern (order some oysters with your cocktail) or Sly Fox Pub at Reynold’s Tavern at the top of the circle. Or, head to West Street and try the local brews at Rams Head Tavern.

For brunch, lovers of the casual will find a locals hangout at Boatyard Bar & Grill, just across the bridge in Eastport. For a more upscale experience, opt for Carroll’s Creek.


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 – Diva and Horse are our two favorite picks for designer clothing. When you reach the top of the street, head to the right, around Church Circle, and continue on to State Circle. You can then stroll down Maryland Avenue, which has numerous 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 PM 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!


  • 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 via Jeffweese]