By Bob Tagert

…sort of. This month’s Road Trip started out as a day trip but by the time we reached Annapolis, we decided to stay the night. It was a good decision all the way around. Having more time in Annapolis is always a bonus.

About forty years ago, when I still had a motorcycle, I would take day trips to the waterfront towns in Maryland. One of my favorite stops was the Swamp Circle Saloon. A bawdy kind of place and very inexpensive. It is no longer there, but we decided to take the drive to see who remained.

Our first stop took us to Deale, Maryland on Tracy’s Creek and Happy Harbor Restaurant. Happy Harbor has been there alongside the creek as long as I can remember. As one comment read, “Great local place that is no frills, but good food with realistic pricing. If you’re looking for a local place to enjoy some live music without breaking the bank, get happy and happy harbor. Try the crushes, there’s enough variety to keep you coming back for a while!” This truly is a view into the life of folks in Deale. Hard working, fun loving people that know what it is all about. Happy Harbor has their own charter fishing operation and story has it the captain always finds the fish. On our day there, the place was standing room only but we found two seats at the far end of the bar. Our bartender was Peggy who is fantastic. Clearly she is part of the fabric which is Happy Harbor. The earlier quote was accurate. The price of the drinks alone encourage you to stay. Once you settle in, it is hard to leave…but we did.

Our next stop was Skippers Pier – across and a short piece down the other side of the creek. When I first went to Skippers Pier it was owned and operated by Captain John B and his wife Sherry. Back then the main building was smaller and they had a small electric train that ran from the kitchen, through the wall tunnel and into the bar delivering an ordered sandwich on a flat car. Today the train is displayed behind the bar and the tracks are gone. The entire operation is much larger now. There is a year round Tiki Bar on the outside dock on the water that is enclosed with large garage doors in the cooler months. Said doors open easily onto the water when the days are warmer. The food is great, the people are fun and the prices slightly higher. I ordered a shrimp basket and Lani had wings. Both were very satisfying. For future reference, I have seen some of the largest Blue Crabs ever served at these tables. This place is very popular especially on nice weekends. If the parking lot is full you can park at the marina lot next door. We were getting more citified as we continued on our adventure.

Our final stop before Annapolis was Pirates Cove in Galesville on the West River. Pirates Cove is a classic waterside restaurant. The outdoor deck is the dock that juts out into the West River and has beautiful boats to occupy the view. When I first discovered Pirates Cove, Joe Williams was the bartender. A magnificent gentleman of some 50-60 years old had been working there since he was a kid. Joe passed away awhile back and is missed. Looking back on it now, these three restaurants seem like a progression. Starting with a laid back, local crowd, moving to the same folks but more new people and finally to the uptown type of place. Same great folks, doing what they like. Moving from the watermen style to the recreational boater.

On to Annapolis! We had secured a reservation at the Calvert House – one of the trio of the Historic Inns of Annapolis – earlier in the day so we headed there first. After some confusion on the check-in process, we settled into our beautiful room (only $118 per night) and charted our course to a couple of our favorite places in this city.

Our next stop was Dick Franyo’s Boatyard Bar and Grill. Back in the day, Patton’s Pub occupied this spot. Technically we are in Eastport, across the Spa Creek Bridge from Annapolis, but still a part of the whole. Today Eastport is referred to as the Maritime Republic of Eastport…and that is a story for another time. Boatyard Bar and Grill is a staple in the sailing heritage of Annapolis…racing that is. The saying goes, Annapolis is a drinking town with a sailing problem! Today the Boatyard Bar and Grill is the hangout for the local racing sailors. These are fair weather sailors as well as frostbite sailors and likely they are the same. When we arrived we took two seats at the bar while another couple slid into the two seats next to us. We talked to them and found out they were there on their boat but lived in Old Town Alexandria. I went out in the alcove where we drop off the Old Town Crier and brought one back for our new friends. I was delighted when they told me that they read us all the time. The food at Boatyard is great – we shared the seafood boil on this trek – and certainly the folks you meet are worth getting to know. This put us in a mood to walk to Davis Pub up the street a couple of blocks.

We ended our trek with a “night cap” at Davis. Visiting this Pub was like starting this trip all over…real locals and a mix of recreational boater and watermen. This is truly a local pub. Small, crowded and noisy. It was a perfect ending to a perfect day.

We couldn’t leave Naptown the next day without a cruise around City Dock and breakfast at Chick & Ruth’s Delly on Main Street. You haven’t lived if you haven’t experienced this joint. It is an icon for sure! The lesson here is…if you plan to follow our footsteps, make the room reservation early and count on it being an overnighter!