A Weekend trip to Annapolis

A Memorable Weekend Escape on Maryland's Chesapeake Bay

by and

Travel Tile Our son who had been a student at Syracuse University, was scheduled to row in Annapolis for the GOES Trophy & the Stagg points trophy against the U.S. Naval Academy and Cornell University rowing teams. This is an annual event that Syracuse University had not won since 2011.

The planning for such a trip was relatively simple - we used to live in the Northern Virginia area (near Washington D.C.) and we had been to Annapolis many times in the past. Good seafood is widely available, and the town is very walkable.

Annapolis City Seal We decided that we would fly into Richmond, VA such that we could visit our cabin in Lake Anna, VA and then drive up to Annapolis on Friday morning. This would allow us to avoid the D.C. "rush hour" and to arrive at our hotel close to check-in time.

Rental car selection was made via Hertz, a hotel selected and with those logistical decisions in place, we were ready to go.

A few interesting facts about Annapolis
  • It was the First Capital of the United States.
  • It is the Sailing Capital of the United States.
  • The City is home to the United State’s Naval Academy.
  • Annapolis is One of least populated State Capitals in the United States.
  • Founded in 1649, Annapolis was originally called "Providence" when settled by the Puritans. It was renamed Annapolis to honor Princess Anne, future queen of England.
  • George Washington officially resigned here as commander in chief of the Continental Army after the Revolutionary War. The Treaty of Paris, which formally ended the Revolutionary War, also was ratified in Annapolis in 1784.
  • If you ever saw the TV series "Roots: The Saga of an American Family" (based upon Alex Haley's book), you may recall that Kunta Kinte was brought to Annapolis and sold as a slave there. Today, a monument to both Haley and his ancestor can be seen on the Annapolis harbor, at the spot where Kunta Kinte first set foot in America.

How we got to Annapolis from Florida   Map

Allegiant Airlines (a very low-cost airline) had recently started flights to Richmond from the Sarasota Airport (SRQ). We have been utilizing Allegiant Airlines for several years now, but in the past we had to drive to the St. Petersburg Airport. Allegiant does not fly this route every day, but often enough for a weekend trip. Their air fares are considerably less expensive than other airlines, so even though they use the least comfortable passenger seats we have ever sat in, the low cost and short flight to Richmond (one hour forty minutes) is too good to pass up!

Where to Stay in Annapolis 

A Memorable Weekend Escape on Maryland's Chesapeake Bay A Memorable Weekend Escape on Maryland's Chesapeake Bay

We had selected the Hilton Garden Inn Downtown Annapolis during our trip planning because of it's good downtown location. As the hotel is located on West Street two blocks from the St. Anne's Parish Church, the City Dock area was only a few blocks away. It also meant that Route 50 was perhaps two miles away, providing us with easy access to either the east or west-bound Interstate.

This was a very comfortable hotel, good sized room with a king bed, large flat panel TV and a large bathroom. Really there was no view, but then we did not require one as our plans called for us to be out & about most of the time.

The hotel provides valet parking only, a wee bit pricey but this meant that the rental car was in a safe location whenever we were not using it.

Hilton Logo

NOTE: Images are the property of Hilton Hotels

As of October 2023, there are over 64 hotels & motels in Annapolis, with a wide range of prices & locations. We wanted to be within walking distance of downtown and the harbor, so selecting the Hilton Garden Inn was simple for us. Your requirements may differ, so click here to view a Google Search Results list for "Accommodations in Annapolis".

St. Anne's Episcopal Church
A Memorable Weekend Escape on Maryland's Chesapeake Bay
A Memorable Weekend Escape on Maryland's Chesapeake Bay
A Memorable Weekend Escape on Maryland's Chesapeake Bay

Our walking route to the harbor area took us past this church, so after we returned to our hotel, we did some research to discover the history of this building.

St. Anne's Episcopal Church is an historic Episcopal church located in Church Circle, Annapolis. It was the first church in Annapolis, founded in 1692 to serve as the parish church for the newly created Middle Neck Parish, one of the original 30 Anglican parishes in the Province of Maryland.

St. Anne's was founded after the passing of the Establishment Act. The Act allowed for the construction of the State House, King William's School, and St. Anne's, though due to the limited work force and insufficient funds, all of the projects were finished much later than expected.

Work on St. Anne's started out slowly. In 1699 the General Assembly specified that the dimensions of the church were to be 65 ft wide (20 m) and 30 ft long (9.1 m) with a porch and a tower that would hang a bell. But due to the insufficient funds, no progress was made until 1700, when the government invested enough money to begin construction.

By 1704, the church was finished, though some changes were made in the structure. It served Chapel River until 1715, when the Province of Maryland was returned to Lord Baltimore. A bell, which would call parishioners to services until it was destroyed by fire in 1858, was donated to St. Anne's by Queen Anne.

Since St. Anne's was often referred to by writers of the time as a "barn" rather than a "proper place of worship", many locals asked the government for a new church in 1775. Their wish was granted, and in late 1775, the church was razed.

NOTE: All Images are the property of Just Traveling Thru, LLC

 More Info for St. Anne's Episcopal Church 
  • St. Anne's Episcopal Church Wikipedia Article:
  • St. Anne's Episcopal Church Website:
  • St. Anne's Episcopal Church Google Images Set:
Maryland State House       Map
Section Banner Image

The Maryland State House is the oldest functioning state capitol building in the United States. This architectural wonder, dating back to 1772, has witnessed pivotal moments in American history, from the ratification of the Bill of Rights to the resignation of President Richard Nixon. Take a guided tour to delve into the building's fascinating past and admire the opulent Senate Chamber and House of Delegates.

In 1783 and 1784 it served as the capitol building of the United States Congress of the Confederation, and it is where Ratification Day, the formal end of the American Revolutionary War, took place.

NOTE: This image is the property of Martin Falbisoner via Wikimedia Commons using the Creative Commons CC BY-SA 3.0 License.

 More Info for the Maryland State House 
  • Maryland State House Wikipedia Article:
  • Maryland State House Google Images Set:
Exploring Annapolis
A Memorable Weekend Escape on Maryland's Chesapeake Bay
A Memorable Weekend Escape on Maryland's Chesapeake Bay
A Memorable Weekend Escape on Maryland's Chesapeake Bay
A Memorable Weekend Escape on Maryland's Chesapeake Bay

All images are the property of Just Traveling Thru, LLC

The heart of Annapolis is dominated by its historic district, where cobblestone streets wind their way past 18th-century homes, leading to the Maryland State House, the oldest state capitol still in continuous legislative use. Nearby, the United States Naval Academy's sprawling campus adds a distinctive military presence to the city.

Annapolis is a very walkable city, and as our hotel was only a half mile from the City Dock area and to get there, all we had to do was to walk east along West Street.

In the fourth image, you can see the City Dock area in the center background, perhaps a 1/4 mile from St. Anne's Parish Church.

A Memorable Weekend Escape on Maryland's Chesapeake Bay
A Memorable Weekend Escape on Maryland's Chesapeake Bay
A Memorable Weekend Escape on Maryland's Chesapeake Bay

All images are the property of Just Traveling Thru, LLC

There are a number of interesting shops on West Street as you walk down the hill to the City Dock area, as well as a number of restaurants. Our goal was to walk to the large number of seafood restaurants gathered around the City Dock inlet. On previous trips to Annapolis, we had good luck with several seafood restaurants, and we were sure that we would find one of them still in business!

A Memorable Weekend Escape on Maryland's Chesapeake Bay
A Memorable Weekend Escape on Maryland's Chesapeake Bay
A Memorable Weekend Escape on Maryland's Chesapeake Bay

All images are the property of Just Traveling Thru, LLC

We looked at posted menus for several restaurants before arriving at the Middleton Tavern, and we decided that this was where we wanted to go because the great smells coming out of the kitchen, coupled with the really good menus and prices, made the decision easy for us!

A Memorable Weekend Escape on Maryland's Chesapeake Bay
A Memorable Weekend Escape on Maryland's Chesapeake Bay
A Memorable Weekend Escape on Maryland's Chesapeake Bay

All images are the property of Just Traveling Thru, LLC

After lunch, we decided to walk off those calories by strolling over to the Naval Academy which was only one block away from the Middleton Tavern. We entered the grounds through the John Barry gate.

Note: Entrance to the Naval Academy requires a photo ID, and as I had left my wallet back at the hotel, we could not enter the Academy. Talk about disappointed, but the hotel was a mile away and we decided that we would forego the Academy tour until another day.

 Admiral John Barry Quick History 

John Barry (March 25, 1745 – September 13, 1803) was an officer in the Continental Navy during the American Revolutionary War and later in the United States Navy. He came to be widely credited as "The Father of the American Navy" (and shares that moniker with John Paul Jones and John Adams) and was appointed a captain in the Continental Navy on December 7, 1775. He was the first captain placed in command of a U.S. warship commissioned for service under the Continental flag.

After the war, he became the first commissioned U.S. naval officer, at the rank of commodore, receiving his commission from President George Washington in 1797.

Click here to read the full history of Admiral Barry.
 More Info for the Naval Academy 
  • Naval Academy Wikipedia Article:
  • Naval Academy Google Images Set:
Annapolis City Dock Area

All the above images are the property of Just Traveling Thru, LLC

As you can see in these images, the Naval Academy is immediately adjacent to the City Dock area, which is always an entertaining place to walk about. Turns out the Annapolis Boat show was scheduled to take place on Sunday, but we did not have the time available to attend.

 Annapolis City Dock List of Amenities 
  • 260’ Reservation Bulkhead (Boats up to 125 Ft)
  • 320’ Bulkhead - First-Come-First-Served (Boats up to 125 Ft)
  • 17 Slips - First-Come-First-Served (Boats up to 60 Ft)
  • 56 moorings for boats up to 55'
  • 20 moorings for boats up to 35'
  • Boater’s Showers with Laundry
  • Harbor Tours and Water Taxi Landing
  • Visitor’s Information Center
  • Annapolis Website for more info
Annapolis Chicken Statues
A Memorable Weekend Escape on Maryland's Chesapeake Bay
A Memorable Weekend Escape on Maryland's Chesapeake Bay
A Memorable Weekend Escape on Maryland's Chesapeake Bay
A Memorable Weekend Escape on Maryland's Chesapeake Bay
A Memorable Weekend Escape on Maryland's Chesapeake Bay
A Memorable Weekend Escape on Maryland's Chesapeake Bay

All images are the property of Just Traveling Thru, LLC

As you can see in these images, the walk back to the hotel from the harbor area was not only pretty but we also ran across some interesting chicken statues.

The Annapolis Chicken Statues are a quirky and beloved feature of downtown Annapolis, Maryland. These whimsical statues, depicting chickens in various poses and styles, are scattered throughout the city's streets, parks, and storefronts. Originally part of a public art project in 2013, the statues have since become iconic symbols of Annapolis's charm and character. Each chicken statue is uniquely designed by local artists, reflecting the vibrant culture and heritage of the city. Visitors can enjoy a self-guided walking tour to discover these charming sculptures while exploring the historic streets and waterfront of Annapolis.

Annapolis Sailor Oyster Bar
A Memorable Weekend Escape on Maryland's Chesapeake Bay
A Memorable Weekend Escape on Maryland's Chesapeake Bay
A Memorable Weekend Escape on Maryland's Chesapeake Bay
A Memorable Weekend Escape on Maryland's Chesapeake Bay
A Memorable Weekend Escape on Maryland's Chesapeake Bay

Image is the property of Sailor Oyster Bar

A Memorable Weekend Escape on Maryland's Chesapeake Bay

Image is the property of Sailor Oyster Bar

As the Sailor Oyster Bar was next door to our hotel, and not only does it get good reviews, but the kitchen smells were amazing, we decided to give it a try.

As you can see in these pictures, this is not a large restaurant! The menu is very good, but may not be for every taste. The trout fish dip (image #3) was excellent !

Celeste had the fish chowder (image #2) and we both agreed that it was excellent. I had the mussels and they were a nice size and came in a broth that was perfect. We both had a white wine, and the dinners were served soon after we had made a dent in the trout fish dip.

We had the chocolate peanut butter truffles for dessert, and they were delicious!

Mike's Restaurant      Map

On a subsequent trip to Annapolis (in July 2022), we discovered Mike's Restaurant and we had a very enjoyable lunch! This place was so good, that it is the type where you say to yourself "this one is a gotta visit again & again!" They are located on the South River waterfront, they have dockage and they have inside and outside seating. They have a really good menu, click here to see what they offer.

The restaurant's nautical-themed decor adds to its charm, creating a cozy ambiance that complements the waterfront setting. Whether you're a local resident or a visitor exploring the historic streets of Annapolis, Mike's is a must-visit destination for those seeking an authentic taste of Chesapeake Bay flavors. With its commitment to quality and a menu that evolves with the seasons, Mike's Restaurant stands as a culinary beacon in the heart of Maryland's capital city, inviting patrons to savor the best of the Chesapeake region's culinary delights.

A Memorable Weekend Escape on Maryland's Chesapeake Bay
A Memorable Weekend Escape on Maryland's Chesapeake Bay
A Memorable Weekend Escape on Maryland's Chesapeake Bay
A Memorable Weekend Escape on Maryland's Chesapeake Bay
A Memorable Weekend Escape on Maryland's Chesapeake Bay
A Memorable Weekend Escape on Maryland's Chesapeake Bay
A Memorable Weekend Escape on Maryland's Chesapeake Bay
A Memorable Weekend Escape on Maryland's Chesapeake Bay
A Memorable Weekend Escape on Maryland's Chesapeake Bay

IMAGE CREDIT: All images are the property of Just Traveling Thru, LLC

 Annapolis 
  • Annapolis Article on the Wikipedia Site
  • Annapolis History Site
  • Google Search Results List of things to do & see in Annapolis
  • Google Search Results List of Annapolis Restaurants
  • Google Search Results List of Accommodations in Annapolis
  • Google Images set for Annapolis
  • Youtube Search Results List for Annapolis, MD
  • Amazon Search Results List for Annapolis, MD
  • Phantoms of Annapolis Ghost Walking Tour from "Get Your Guide"
  • Visit our Youtube Channel
  • Our Image Gallery for Annapolis
  • Wikipedia Article for Annapolis
 Naval Academy 
  • Naval Academy Website
  • Naval Academy Wikipedia Article
  • Visit Annapolis Academy Page
  • Naval Academy Visitor Center Page
  • Naval Academy History Page
  • Naval Academy Search Results List for Youtube

 

Expedia Advertisement
 

Disclosure: Some of the links on this page are Affiliate Links, meaning, at no additional cost to you, that we will earn a commission if you click through and make a purchase. So we would appreciate any click throughs, if you are inclined.

Note: All images on this page are the property of Just Traveling Thru, LLC unless otherwise noted.

Note: If you are interested, click here to view our European Travel Tips & Warnings. Or to take a look at our methods for planning, click here to view our Trip Planning Page..

 
 

To review any of our content, make suggestions and/or comments, please click the "Info" menu button at the top of this page. You will find our "Contact Us" link on that drop-down menu.

 
Matomo Link