9 Quirky Romantic Things to Do in Baltimore For American History Buffs

WHY GO: What are the most romantic things to do in Baltimore for history buffs in love? We’ve got plenty of ideas – weird and not so weird – starting with The Flag.

The Flag. Yes, ours. The one we sing about in the Star Spangled Banner was sewn and originally sent up the pole in Baltimore. So a visit to Baltimore MD, the “Monumental City,” wouldn’t be complete without seeing where Old Glory was stitched and flew proudly.

Chances are you’ve been here already. At least to the more commercialized Baltimore Inner Harbor where the National Aquarium, Maryland Science Center the Baltimore Maritime Museum, and a myriad of shops and restaurants draw year round tourists like ants to a picnic.

But this Getaway takes you to some lesser known attractions and neighborhoods. To a Dentistry Museum that features George Washington’s teeth. To the Birthplace of American Railroading (and its corporate office, now a boutique hotel). And to the Jewish enclave of Lombard Street.

You don’t have to look very hard to find historical and “Offbeat” Baltimore. For a longer stay, combine this Getaway with a Baltimore City Arts and neighborhoods focused visit, where we cover Harbor East, Federal Hill, the world class Baltimore Museum of Art and Walters Art Museum, the Johns Hopkins U. Library (a hidden stunner), and more for an artsy Baltimore Getaway.

Together, these two Baltimore Getaways have made it on our Best Romantic Getaways in Maryland post.  

Romantic Things to Do in Baltimore

VISIT: Star Spangled Banner Flag House

Before you even step foot inside the Star Spangled Banner Flag House consider that the flag built into the front wall of the building is the same size as the one observed by Francis Scott Key on September 14, 1814 as he penned The Star Spangled Banner from a boat just off Fort McHenry.

When war was declared two years earlier, the Army in Baltimore requested an “ensign” large enough to see from afar. But, who would stitch it? Mary Pickersgill’s family had a long history of sewing “colors” and sign flags for merchant ships. (Quite possibly competing for the same jobs as Betsy Ross up in Philadelphia).

For this purpose Pickersgill was asked to craft an American Flag 30 ft. X 42 ft. Each stripe had to be two feet wide, and 15 stars two feet each from tip to tip. She managed to get the job done in six weeks.

A visit to this museum complex, “where inspiration was sewn,” includes a tour of Pickersgill’s original circa 1793 home in its original location, exactly where she spent those 6 weeks sewing the fateful flag.

With floorboards and windows over 200 years old, and samples of Old Glory folded in her workroom, it’s a thrilling look at a perspective of US History we don’t ordinarily consider.

The flag that Mary made still exists. Although you won’t find it here. To see it, you’ll have to head down to Washington, DC and the Smithsonian Museum.  Check website for days open, hours, and fees.

VISIT: Fort McHenry

Baltimore owns a “key” place in our nation’s history. The bombardment of Fort McHenry by the British during the War of 1812 inspired an observer, Francis Scott Key, to write the words that would become our Star Spangled Banner.

One of the most uplifting moments of the tour comes just after watching a short movie in the Visitor’s Center, when you are invited to stand to sing the national anthem as curtains open to reveal an American flag flying right outside. It’s worth visiting Baltimore for that spine-tingling moment alone. Check website for hours and admission fees.

TOUR: Self-Guided Driving Tour

To get the most out of a Historical Baltimore visit, download this turn-by-turn sightseeing guide taking you from the Visitor’s Center at the Inner Harbor and exposes you to other, lesser known Baltimore neighborhoods.

Learn about the USS Constellation, which was the last all-sail ship used as a Naval Academy Training vessel, and the Reginald Lewis Museum of African American History and Culture .

Along the cobblestone streets of Fells Point, discover the mustering site for Massachusetts Civil War recruits, the bar favored by Edgar Allan Poe, and the row of homes that Frederick Douglas purchased after he escaped slavery, disguised as a seaman.

“When I left Maryland, I was property.  When I came back, I bought property,” Douglas was purported to have said.

Mount Vernon – Baltimore Style

You’ll drive through Little Italy, “Cornbeef Row” – the Jewish section and home to the third longest-standing synagogue in the United States, and the monument studded Mount Vernon, arguably the most beautiful area of Baltimore.

The 178-ft. marble column and statue of George Washington completed in 1829, was the first monument in the country to honor a United States President. When outgoing President, John Quincy Adams, came to town and saw the Washington Monument, he declared Baltimore, “The Monumental City.” The name stuck.

The adjacent gothic spire Methodist Church and a central city garden creates a tableau that appears elegantly European. This area unfortunately gets lost in the whole harbor thing,” says in-the-know locals.

VISIT: Samuel Harris National Museum of Dentistry

There may be other Dentistry Museums (who knew?), but this one, the Dr. Samuel D. Harris National Museum of Dentistry opened in 1996 on the University of Maryland campus, is the largest in the country. That’s probably because the world’s first dental school, The Baltimore College of Dental Surgery, opened here in 1840.

At first, you may think a museum dedicated to a dreaded medical procedure would be blah, boring, or even trigger-stressful. But I ended up staying much longer than the 20 minutes I’d allotted because it is so fascinating.

George Washington’s Dentures

The most prominent – and myth-busting – artifact on exhibit is an actual set of George Washington’s dentures. And they are not made out of wood, as countless teachers have taught us. Composed of sculpted bone and hinged wire, they were so uncomfortable, Washington had to have new sets made often.

The museum lobby features a stained glass window of the “Patron Saint of Tooth Sufferers,” Apollonia, from a church in Wales, next to portraits of same by Andy Warhol.

Visitors are invited to “Share Your Smile” – via digital camera that snaps a photo and then adds it to the roster of rotating toothy faces above.

There’s a “Guess The Smile” interactive that questions your ability to identify a celebrity based just on his or her grinning mouth.

Traveling Dentists

Prior to the mid 1800’s, dentistry was not considered a part of the medical field. Traveling dentists made a living helping tooth pain sufferers in small rural towns. A “well-supplied traveling dentist’s outfit, carried in saddlebags” is on display here.

Learn interesting Victorian-age particulars about dental health – such as the not so surprising fact that the upper class displayed wealth by owning personalized sets of tooth scalers (implements that scrape plaque from teeth). In fact, you can get a close gander at Queen Victoria’s mother-of-pearl-handled set.

Doc Holiday

The museum owns one of the only authenticated photos (if not the only photo), taken in 1875, of Dr. John Henry “Doc” Holliday performing a dental procedure. That well-preserved photograph was discovered while cleaning trash out of a classic car in 1991. Check website for hours and admission fees.

VISIT: Jewish Museum of Maryland

*FYI – The Jewish Museum of MD will be closed for renovations until Summer 2024. Check Website for reopening date.

The Maryland Jewish Historical Society was formed in 1960 to save the Lloyd Street Synagogue. The first synagogue built in Baltimore, in 1845, it housed the Orthodox Baltimore Hebrew Association.

The Lloyd Street shul is now part of the Jewish Museum of Maryland. Stories and “Voices of Lombard St.” are told through poster-sized photographs, text quotes and objects in the museum’s poignant permanent exhibit.

Life on Lombard Street

Though specific to Jewish life in Baltimore, The Voices of Lombard St. speaks to a more universal immigrant experience, when newcomers are totally out of their element and ethnic groups must help each other.

“My grandparents had no life after they got here. They were unfit for American life. And I think this was common among these immigrants. Their purpose was to open up the world to their children.” – Joseph Hirschmann.

“The Haves had to help the Have Not’s. It was a simple matter of justice.”

Anyone – Jewish or not – who grew up in Baltimore’s Jewish neighborhood will experience a strong sense of nostalgia here. “I thought the whole world was Italian and Jewish,” wrote a Lombard St. resident.

Prevailing Customs

Exhibits illustrate the prevailing customs of Baltimore’s Jewish population. There’s a picture of a fish in a bathtub, exemplifying the practice of keeping carp fresh before being ground and cooked as gefilte fish. And a photo montage of markets and butcher shops illustrate crowds of women shopping and preparing for the Jewish Sabbath and holidays.

At some point, Yiddish Theater and deli’s give way to riots and drugs, ultimately forcing Jews to move to safer places. Plan to spend a half hour or more here if you want to read all the signage. Even if you didn’t live here, and have no connections to Baltimore, it’s an emotional look at an immigrant group who made the best of a new country and new world.

VISIT: B&O Railroad Museum

In 1827, Maryland State Legislators granted a charter to build a “road of rails” between Baltimore and the Ohio River. The “railroad” was, at the time, a new technology, conceived to compete with the New York Erie Canal. Maryland’s State government was taking a big chance that obviously paid off.

The 40-acre B&O Railroad Museum tells the story of railroading from the place of its origins.

Most of the train cars are arrayed within Baldwin’s Roundhouse, the largest circular industrial building in the world at the time of its construction in 1884. The roundhouse’s 245 feet interior diameter was designed to accommodate the largest passenger cars of the day.

Now, enormous train cars radiate like spokes from a wheel inside this colossal building. You can jump aboard each one, and then avail yourself of various tours through the day.

“The War Came By Train” exhibit illuminates the way this new technology influenced the outcome of the Civil War. Outside, walk through retired train cars – some set up with model-train dioramas, others available to ride. Check website for dates and times open, and for admission fees.

DO: Take The Baltimore Water Taxi 

The Baltimore Water Taxi ferries beau coups visitors to 17 harbor access points, for just $12 per day.  On an ideal afternoon, it’s the best place to chill out on the water. Even if you have no desire to get off.

DO: Catch A Game at Oriole Park at Camden Yards

Are you an Oriole’s Fan – or is your team playing them during your visit? Rooting for your guys at Oriel Park at Camden Yards is a perfectly romantic thing to do in Baltimore if you’re both into the baseball summer night scene.

Old School Restaurants in Baltimore MD

EAT: Sabatino’s, Little Italy

In all the hoopla about the hottest new restaurants, sometimes its nice to shine light on those that have stood the test of time. Sabatino’s – opened in 1955 and still a Little Italy landmark – is one such “old school” institution. It’s got friendly service, traditional “red sauce” Italian cuisine, and white linen table-set dining rooms.

Known for its homemade salad dressing on the signature Bookmaker Salad, Sabatino’s also serves up full and half-orders of Lasagna, Penne Vodka, Baked Ziti, and Eggplant Parm ($15-$19) like Mama used to make. All are hearty, fresh and delicious.

EAT/BREAKFAST: Miss Shirley’s

Many Baltimore natives will send you to Miss Shirley’s for your morning meal: providing you have enough room in your stomach for some serious eats. With portions designed to share, the savories win out. Battle Of the Brunches bestowed best dish on Crab Cake and Fred Green Tomatoes, though Shirley’s Affair with Oscar – Beef Fillet with Crab has won numerous awards.

EAT: Woodberry Kitchen

A perennial hotspot in the gentrifying outskirts of town, Woodberry Kitchen is tucked into the repurposed Clipper Mill complex. With an outdoor patio strung with lights, flickering votives,  wood beam interior a hermit’s cabin gone wild, Woodberry has the atmosphere and quality of locavore food that keeps the reservation phones a-ringing.

EAT/DRINK: Pick a place in Fells Point

The oldest section of Baltimore charms you with brick sidewalks and cobblestone streets. Fells Point has been Baltimore’s go-to neighborhood for food and drink –  and carousing – since 1763. A party every night. With bars named The Cat’s Eye Pub, Ale Mary and One Eyed Mikes, and Bad Decisions, you can’t go wrong stumbling in to any and all.

Historic Stays in Baltimore MD

STAY: Baltimore Hotel Monaco

Initially the B&O Corporate Headquarters, the 1906 Beaux Arts Hotel Monaco is just three blocks from the Inner Harbor.  A bit more sedate than the typical crazy-cat Kimpton Hotel décor, the multi-nook lobby is a quiet-riot of maroons, dollar-bill greens, and ecru, punched up by flashes of chartreuse. Here, every evening, guests join a convivial complementary Wine Hour.

High ceiling guest rooms are perfect lairs for CEO’s and those who like to travel like them. Rich blue leather headboards on Frette linen enrobed beds, red lacquer desks, Poupon-yellow leather walls in dark marble baths, the Monaco caters to lovers of the colorful.

STAY: Lord Baltimore Hotel

Another historic hotel three blocks from the inner harbor, the Lord Baltimore was the centerpiece of upscale Baltimore hospitality when it opened in the late 1920’s. Rubell Hotels purchased the property in 2013 after it faded and fell out of favor. The common areas and most of the guest rooms were redesigned. Rooms are handsomely masculine and cool. And at this point, reasonably priced for the area.

More Weekend Getaways Near Washington DC

• Annapolis MD: Midshipmen, Ahoy!
• Montgomery County MD: Urbane Just Outside Washington DC
• Fairfax County VA: George Washington’s Home Is Just The Start
• Loudoun County VA: Washington DC’s Rich Wine Region
• National Harbor MD: Fun DC Area Town Established 2008
• Frederick MD: A Mini-Philly With a Charm All Its Own
• Baltimore MD: The Arts and Neighborhoods In Charm City

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