Labor Day Events

Annapolis & Baltimore

Hello Watermark® Community! If you are searching for things to do this upcoming holiday weekend, look no further! We have a variety of Labor Day events to choose from in both Annapolis and Baltimore, ranging from a scandalous tour to live music cruises to a full-day excursion to St. Michaels.

Annapolis

Sip a delicious beverage and soak in the views.

What better way to unwind than on the water? Our 40-minute Annapolis Harbor & USNA Cruise features a narration of the city’s history, beautiful scenery, and a full bar* on board. This cruise is a local favorite and fun for the whole family.

If you are searching for a longer activity, we have 90-minute cruises that take you up the Severn River, under the Chesapeake Bay Bridge, and out to the Thomas Point Lighthouse. This is a great way to see the Chesapeake’s landmarks from a whole new perspective. Make sure to have your camera ready!

Our full-day excursion to St. Michaels is a wonderful day trip. Sip a mimosa, bloody Mary, or your favorite morning cocktail* as you cruise to this quaint town. During your approximate 3 hours ashore, visit the Chesapeake Bay Maritime Museum (admission included with ticket), try the local seafood, and peruse the boutique shops. Then, enjoy a nice cruise back to Annapolis.

Photo by AD Photography.

Dance the night away on a live music cruise.

On both September 4th and September 5th, climb aboard for our Annapolis Sunset Cruise with Live Music. This 90-minute cruise is such a fun time! Dance with your friends, relax with a cool drink* from our River Run Bar, and enjoy the spectacular view.

September 4 – Top Dead Center

September 5 – Sharon & the Edge

Walk the historic streets of Downtown Annapolis.

Our period-attired guides will share the city’s rich history on our Colonial Annapolis & USNA Walking Tour. You will hear stories of Colonial life, Maryland’s signers of the Declaration of Independence, and more as you visit significant locations such as the Maryland State House and the U.S. Naval Academy.

On September 5th, join Scandalous Annapolis. This adults-only, lighthearted, tongue-in-cheek, walking tour is presented by a guide in the character of a colonial indentured servant who works odd jobs day and night to make ends meet – colonial style. Hear scandalous anecdotes and jaw-dropping tales about what went on inside Annapolis’ famed homes and taverns.

Baltimore

Discover Baltimore’s Inner Harbor.

Available Thursday-Monday, our narrated  Baltimore Harbor Cruise is a fantastic way to explore the Inner Harbor. In 45 minutes, you will hear the city’s history as you cruise by famous landmarks including Fort McHenry, the Key Bridge, the Domino Sugar Sign, and more.

For a fun night out on the town, join our City Lights Cruise on September 4th and 5th. During this 90-minute cruise, you will see the lights of the city reflected on the water to the tune of a fun music playlist.

Explore Frederick Douglass’ early life in Baltimore.

On September 4th, embark on the journey of the young enslaved Freddy Bailey on our Becoming Frederick Douglass walking tour in Baltimore. During his time here, he was influenced and inspired to ultimately spread the word of the evils of slavery as the most famous abolitionist orator. Walk the streets with our period-attired guide as you step back into the early 1800s and learn about the first book he purchased, the streets he lived on, the shipyards he worked for, and the houses he later purchased as a free man. This tour is offered in partnership with the Kunta Kinte-Alex Haley Foundation, which receives 20% of the proceeds.

*Alcoholic and non-alcoholic beverages and snacks available for purchase.