By Bob Tagert

Over the years we have made many trips to Annapolis…by automobile and by boat. The sail into Annapolis is beautiful. Coming up the Chesapeake Bay, you make a port run into Spa Creek. On the starboard side is the capitol of Maryland, Annapolis. On the port side will be the town of Eastport and the Spa Creek Bridge connecting the two vibrant towns, and fittingly, the name of the street is Compromise Street. A bit farther “inland” and not in view from the water is West Street – a lessor visitor-frequented side of the town even though that is where the Visitors Center is located.

East Side…

The town of Eastport was established in 1868 and annexed into the town of Annapolis in 1951. Eastport continued to wallow under the shadow of Annapolis proper until the uprising on Independence Day, Sunday, January 25, 1998.

Like any great movement, the concept for the Maritime Republic of Eastport began in a local pub over a couple mugs of beer. The prime mission was to find a creative way to promote and encourage the patronage of Eastport businesses that were destined to be hurt by a three-week closing of the Spa Creek drawbridge that connects the two towns while much needed maintenance took place.

What started as a stunt to draw attention to the town of Eastport, became a labor of love as the community rallied around the town and fundraisers were started to benefit the residents. Today that spirit is still celebrated with the annual Tug of War across Spa Creek between Annapolis folks and the Eastportaricans. They even have their own flag emblazoned with a coat of arms flanked with “rampant retrievers” and the motto, “We Like It this Way!”

Once in Eastport, Severn Avenue is one of the main drags and leads to some of the best restaurants in Eastport. While three of the areas popular chain restaurants – Blackwall Hitch, Charthouse and Ruth’s Chris – are located on the Eastport side of the creek, we prefer to frequent the locally owned eateries. The iconic Davis Pub on Chester Avenue and the Boatyard Bar & Grill – the local sailors gathering spot remain our favorites. Other popular locally owned places the likes of Lewnes’ Steak House, O’Learys Seafood Restaurant and Carrol’s Creek Café welcome locals and tourists alike with prime steaks and seafood and lots of atmosphere. On this trip we noticed “new to us” Adam’s on Fourth (opened in 2023) and Forward Brewing (opened in 2020). How in the world they just got our eye on this trip is amazing since we’ve driven by them more than a few times these last 6 years. Maybe because the day we were there was a beautiful Saturday afternoon and the whole town was abuzz. In any case, we are going to check them out on our next trek.

In addition to great places to eat and drink, there are also some very cute shops and on the other side of Eastport on Back Creek, you can entertain yourself at the Annapolis Maritime Museum – very well worth the stop! The streets in Eastport are pretty narrow so bring the compact car if you have one or be prepared to pull your sideview mirrors in on occasion.

Everywhere you look there is water from the creeks or the Chesapeake Bay itself. It is beautiful and very, very dog friendly.

West Side…

The main purpose of this Road Trip was to see the Eastport Oyster Boys perform their musical magic at the beautiful Maryland Hall off of West Street in Annapolis. The EOB’s are a very popular Annapolis/Eastport-based band known for their “modern maritime music” celebrating Chesapeake Bay life, history, and culture with folk, Celtic, and rock influences. Officially appointed as Musical Goodwill Ambassadors for Annapolis and the Maritime Republic of Eastport, they entertain with witty songs and stories, promoting a philosophy of ” a good hat, a good dog, and a good boat”. The event we attended was the band celebrating its 30th anniversary with a “Shuck it Tour” and benefits for local musicians.

Like many of you, we haven’t spent a lot of time on the West Side over these last 38 years so our first-hand knowledge of the many eateries and shops in this part of Annapolis is very limited. Basically, Ram’s Head Tavern and Stage – for food and to watch a show – and the Visitors Center were the only two destinations we seeked out. This time, however, we spent the night at The Westin Annapolis at 100 Westgate Circle (we usually stay at the B&B above Chick & Ruth’s on Main Street near City Dock) located quite aways up West Street but near Maryland Hall. It is much the same as any luxury hotel and a nice place for an elegant, quiet stay – not usually our M.O. when we are in town – and we enjoyed every bit of our evening there and treated ourselves to breakfast at Miss Shirley’s Café just around the corner from the hotel. More on it in the “Dining Out” section of this publication.

While I’m not sure how I feel about AI generated info, I believe what I found to be good information. Not being familiar with any of the following, I find it quite interesting and it gives me a different perspective on the importance of this street.

Historically, West Street was the only land-based entrance into the “city of sails” for travelers arriving by horse or carriage from Baltimore, Philadelphia, or Washington, D.C.

Even though we have been in the Visitors Center several times, I guess I didn’t pay any attention to its story. The Claude House, located at 26 West Street, is the circa 1767 building that serves as the Annapolis Visitors Center. It was originally owned by Dennis Claude and is a key marker of the street’s colonial industry and commerce. Lots of other historic buildings in this area as well.

By the late 1800s, the street housed a rail depot for the B&O Railroad’s Bay Ridge branch, which ran through what is now Amos Garrett Boulevard.

In the segregated 1950s, the first block of West Street became a unique cultural intersection. It functioned as a commercial sanctuary where African American residents could shop at Jewish-owned stores during an era when many other merchants refused them service.

The surrounding area, originally farmland, was incorporated as the town of West Annapolis in 1890 before being annexed into the city in 1951. This annexation led to several street name changes to avoid duplication (e.g., Severn Avenue became Melvin Avenue).

Like many downtown areas, West Street’s commerce suffered following World War II due to the rise of suburban shopping malls. It began a significant recovery during the 1990s boom. Today, the first few blocks are known for a vibrant mix of art galleries, restaurants, and entertainment venues, maintaining their historical brick-covered aesthetic while serving as a center for local nightlife and tourism.

We encourage you to take the time to check out what the West Side offers the next time you are in Naptown!

All Around Town

When planning this trip, our concentration was on Eastport and West Street since they are “around” Annapolis. Much like Alexandria, Eastport compares to Del Ray and The West End compares to West Street with Old Town in the middle. However, there’s no way we could avoid heading down to City Dock and hitting up a couple of our favorites before we left.

On par for a nice weather day, the waterfront was bustling. With construction going on in the major parking lot, we were unsure we would be sticking around but lady luck was with us and we found a spot in the heart of lower Main Street. We didn’t have a lot of time but split what we had between two long time favorites – Middleton Tavern and O’Brien’s Oyster Bar & Seafood Tavern. We have a lot of history with both places and there is still always a friendly face when we show up. Had to have a Natty Bo oyster shooter at Middleton and some crab dip and a couple of sailor drinks at OB’s. We were pleasantly surprised to find out that one of our former Bond 45 servers – Sierra – is now working here! Another good reason to go back!

City Dock, Eastport and West Street are all doable in a long day trip but I encourage you to spend a night if you can. Lots of great places and varying $$$ to pick from. As the weather grows nicer, go in the middle of the week to avoid the crowds!