Pets, Places, & Things, Road Trip

Annapolis, Maryland

By Bob Tagert

Annapolis Maryland


         I have sailed in and out of Annapolis many times over the past 25 years. Maryland’s capital sits alongside the Chesapeake Bay, the largest estuary in the United States, spanning 64,000 square miles and six states and offering sailors everything from quiet retreats in calm inlets to national and international sailing regattas in open water. Even though the last part of February is arguably sailing weather with balmy temperatures and plenty of wind, we still opted to drive to this maritime town for our monthly road trip.

Like Alexandria, Annapolis is a seaport town, and like Alexandria there are many great shops, museums and restaurants. We timed our trip to Annapolis so that we would be there when Kevin Brooks, a close friend, was playing music at Castlebay, a traditional Irish Pub. With March being the month of the Irish (and my birthday), we thought this is a good month to write about our neighbor and the Irish.

Getting to Annapolis is very easy although traffic can sometimes be a problem. Just get on the beltway to Route 50 and head east. In less than an hour you will hit the turn off for “Naptown”, a favorite moniker used by the locals. Like Old Town Alexandria, the main street in Annapolis runs perpendicular to the water. The main street is one way so all traffic begins around Ego Alley, the canal that runs from Spa Creek into the city. Here is where you will find all of the sailboats and powerboats that were first come first served at City Dock. Others will be tied to mooring balls or anchored in the harbor.

Metered parking is also available around the city dock and this is where the shops and restaurants begin. Bars and restaurants are plentiful and are usually very busy, especially on warm spring days. Mussels and little neck clams are always a favorite at McGarvey’s Saloon and Oyster Bar. Established in 1975, McGarvey’s was recently purchased by three midshipmen. This is quite a coincidence, since three Lt. JG’s originally started the Chart House Restaurant group when they bought their first restaurant in Aspen, CO. One of the most beautiful Chart House Restaurants sits across Spa Creek from Ego Alley. This is the first Chart House I ever experienced and is still my favorite.

Across from McGarvey’s is Middleton Tavern, which has always been a popular destination. This tavern is one of the oldest continuously operating taverns in America and was originally established in 1750. The history is amazing and worth looking up. As it is with a lot of places in Annapolis, there is usually live entertainment to be found. Other restaurants along Ego Alley include the new Mission BBQ, Dock Street Bar & Grill and Pusser’s Caribbean Grille on the other side of Ego Alley…a great place to people and boat watch and home to the famous Soggy Dollar Pain Killer!

      At the end of Ego Alley is the Annapolis Market House, a food court of sorts with open vendors. Opened in the 1780’s the old Market House was destroyed by Hurricane Isabel in 2003. It took 10 years to reopen and is thriving today. Outside of the market is a brightly colored upright piano that anyone passing by can play. It was enlightening to hear some of the music floating through the air.

Walking one block up Main Street and passing many other restaurants and shops you will come to O’Briens Oyster Bar & Restaurant. In the 70’s Fran O’Brien, a popular defensive lineman for the Washington Redskins back in their glory years, purchased the restaurant. The steak and seafood menu became a favorite amongst the legislators, businessmen and politicians, a distinction it still enjoys today.

In 1993, Jerry Hardesty, the owner of Middleton Tavern took over ownership and operations, changed the name to O’Brien’s and brought back the emphasis on Chesapeake Cuisine. For a time we distributed the Old Town Crier to Annapolis (which we will start again) and O’Brien’s was one of our favorite places so we had to visit this trip. What a surprise, one of our favorite bartenders was still working there from the early 90’s…Gordon McKenney (see how those Irish names keep popping up). It was great catching up. These are the experiences that make it all worthwhile!

   Continuing on up Main Street you will pass Hillman Parking Garage off to the left as well as a number of shops. In the next block you will find Chick & Ruth’s Deli, one of the most popular places to eat in Annapolis. They have everything from a classic breakfast to an incredible crab cake. They also have the Colossal Sandwich Challenges. On our visit we sat next to a nice couple (Harry Blair from Woodbridge, VA and Nakia Craig from Waldorf, MD). Harry was participating in one of said challenges – eating a 3-pound, 3-patty cheeseburger in an hour. We left before he was done but understand that he did not finish in the allotted hour and later lost his lunch. Gotta give him an E for Effort!

Continuing up Main Street toward Church Circle, you will again encounter many fine shops and restaurants. We stopped in to Castlebay Irish Pub, which is also the subject of our dining out this month. This is a great place to grab a pint and listen to some fabulous music. As I mentioned earlier, there are a number of music venues in Annapolis but more importantly, the musicians are very talented across the board.

Besides strolling around town and taking in the sights like the Kunta Kinte-Alex Haley Memorial at the foot of Main Street, Annapolis also offer bay tours, boat rentals or you can always get away by taking a sail on the 74-foot wooden Schooner Woodwind. The Woodwind offers two-hour sailing cruises as well as Sunset Sails. If you are lucky, you might encounter our personality profile, Kevin Brooks, entertaining throughout the sail.

This is just a small sample of what awaits you in Annapolis. It is truly one of the best destinations in our region for simply getting away from the city in under an hour if the traffic Gods are with you.

March is shaping up to be a great month to get out and enjoy an early spring. Take road trip!

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