Baltimore Insider

Baltimore's love landmarks: Spots with a history of romance -- and heartbreak

Ashley Ryan and Paul Hutson at the Four Seasons Hotel, a popular spot for proposals and weddings in Baltimore.

A special table in Little Italy that has been the spot for more than 400 proposals in the past 15 years. A thriving corridor that was once the scene of countless dates and special occasions for the city's African-American community. And a rooftop terrace fit for a Ravens star to pop the big question.

It turns out, the Baltimore region is actually pretty romantic, according to local experts and historians. Throughout the years, the area has been home to a number of memorable love stories (and the occasional not-so-blissful breakup). In fact, at least two events this weekend will be dedicated to exploring the city's romantic past — the Haunted Hearts Pub Tour in Fells Point and Baltimore Heritage's Mount Vernon Love Stories tour.


In honor of Valentine's Day, here are some of the region's love landmarks, and the stories of romance — or heartbreak — behind them.

Will Smith and Jada Pinkett at their 1997 wedding at the Cloisters.

The Cloisters


10440 Falls Road, Lutherville-Timonium

Close to 20 years later, and the wedding of Will Smith and Baltimore native Jada Pinkett still has potential clients inquiring about renting out the castle just north of Baltimore.

"They are probably the highest profile couple we've had," said Annie Applegarth, director of facility operations of the Baltimore Office of Promotion & the Arts, which runs the property.

Pinkett and Smith married at the Cloisters on New Year's Eve 1997. She wore a champagne-colored Badgley Mischka wedding dress; he wore a matching champagne colored suit.

Decades before the Pinkett-Smiths, the Cloisters was a landmark for another prominent Baltimore couple. Sumner and Dudrea Parker, who met as students as Johns Hopkins University, built the castle as their summer home in the 1930s. Sumner Parker was president of a steel company and did ironwork on buildings throughout the area — including the Cloisters.

Gramercy Mansion

1400 Greenspring Valley Road, Stevenson

The mansion, which is located in a forest atop a hill in Stevenson, owes its existence to a marriage. Alexander J. Cassatt, president of the Pennsylvania Railroad, started construction of the property in 1902 as a wedding gift for his daughter Eliza. The 25-room mansion with servant quarters and an 18-horse carriage house was completed in 1906 — after Cassatt's death — and sold in 1907.


Now the bed-and-breakfast is the site for a number of romantic occasions, according to Shannon Rice, assistant manager and on-site wedding officiant for the property. Rice touted the Tudor architecture, authentic period furniture, perfectly manicured lawns and enchanted gardens as reasons why the property bursts with romance. Need more? Chef's Expressions is catering a special five-course Valentine's Day dinner at Gramercy with wine pairings for $99.95 per person (find more info at

The Four Seasons

200 International Drive, Harbor East

Four Seasons Hotel Baltimore has been the site of a number of upscale weddings and proposals since it opened in 2011 — none more memorable than when Ravens kicker Justin Tucker popped the question to his then-girlfriend (now-wife), Amanda Bass, in 2013.

The evening started off at the hotel's restaurant Wit & Wisdom. Then Tucker excused himself from the table and went to the rooftop terrace, which had been transformed into a sea of votive candles. When Bass arrived, members of the band All Time Low played "Marry Me" by Train.

"It was gorgeous," recalled Marama Nengel, the hotel's concierge supervisor. "It's the most breath-taking view of the Inner Harbor. It's magical with the skyline in back of you."


Pennsylvania Avenue

Pennsylvania Avenue was the epicenter for black culture and entertainment in Baltimore around the mid-20th century, so it's no surprise that the area was also a popular date site for couples, according to Wanda Q. Draper, executive director for the Reginald F. Lewis Museum of Maryland African American History and Culture.

"It was undoubtedly the site of many first dates due to the fact that it was the cultural heart and entertainment capital for African-Americans living in Baltimore," she said. "You had the Royal Theatre, and all of the popular bars and restaurants. Most of the entertainment that came to Baltimore performed along Pennsylvania Avenue."

Draper highlighted the Sphinx Club as another major hot spot. (Both the Sphinx and the Royal Theatre are now closed.)

"My parents went there," she said. "It was the ultimate and the hot date and party spot for couples. It was a special occasion, and they dressed to the nines."

Baltimore Coliseum


2201 N. Monroe St., Baltimore

The Center For Urban Families doesn't necessarily shout romance. But back in 1930s through early 1960s, when the site housed the Baltimore Coliseum, it was considered a ideal first date location — particularly for young African-Americans, according to Draper.

"That was the place to go for roller skating or concerts. The big thing to do for dates was to go to the Coliseum. People got engaged there. People met there, fell in love there," she said. "There were a lot of rules and regulations about dating in the black community. Movie theaters were dark. The Coliseum had bright lights and music. Families considered that a safe place to go."

Bromo Seltzer Arts Tower

21 S. Eutaw St., downtown

The Emerson Bromo-Seltzer Tower, the soaring clock tower near Camden Yards, has recently become "quite a hotbed" for proposals, Applegarth said. But most people don't know that the man behind the property, Captain Isaac Emerson, had a somewhat rocky romantic past.


Emerson, the inventor of the headache remedy Bromo Seltzer, had a mansion built for his family at 2500 Eutaw Place in 1895. But when he and his wife divorced, things turned spiteful. As the legend goes, Emerson had a gargantuan building constructed to block the mansion's — and his ex-wife's — view of Druid Lake.

"He deeply loved the women he loved. But when he was done, he was done," Applegarth said.

The Peabody Library

17 E. Mount Vernon Place, Mount Vernon

Although philanthropist George Peabody was twice unlucky with love — two of his engagements were broken off — his affection for Baltimore resulted in the creation of one of the city's most popular wedding venues: The George Peabody Library.

When Peabody's brief engagement to Rhode Island socialite Esther Hoppin ended in 1837 — his second failed attempt at marriage — he turned his attention to philanthropy, according to historian Jamie Hunt, who will lead participants to the Peabody Library and other spots during the Mount Vernon Love Stories tour.


"He intended it as a gesture and recognition for a city that was deeply divided because of the [coming] Civil War," Hunt explained.

Peabody opened The Peabody Institute, and went on to donate millions of dollars for development projects through the course of his life.

"His failure at marriage was a great benefit to Baltimore and other cities throughout the country," Hunt said.

The Belvedere

1 E. Chase St., Mount Vernon

The Belvedere was at the center of Baltimore's social scene in the early 1900s — and has ties to some of Baltimore's most well-known romances.


The famed Wallis Warfield Simpson, the Baltimore socialite whom King Edward VIII abdicated his throne to marry, frequented the location throughout most of her adult life. Her first wedding, to pilot and naval officer Earl Winfield Spencer Jr., took place blocks away at Christ Episcopal Church in 1916, according to Hunt.

The Belvedere also became the scene of many raucous nights for author F. Scott Fitzgerald, who came to Baltimore with his wife, Zelda in the 1930s when she was treated for mental illness at Johns Hopkins Hospital's Henry Phipps Psychiatric Clinic. He wound up leaving Baltimore in 1936 after throwing a debut for his daughter, Scottie, at the Belvedere Hotel, Hunt said.

The Horse You Came in On

1626 Thames St., Fells Point

The popular Fells Point watering hole was a favorite of the late writer Edgar Allan Poe, according to historian Cliff Long, who leads Baltimore Ghost Tours' Haunted Hearts Pub Tour. During a stop at The Horse You Came in On, which Poe lived about five blocks away from, Long tells tourgoers the story of Poe's six-week romance with next-door neighbor Mary Devereaux.

"He was a rather jealous suitor," Long said before going into a story about Poe "flying into a rage" when the woman said "hello" to a friend of her brother.


After weeks of ignoring Poe, the woman's uncle opened one of his insult-riddled letters, which led the uncle to order Poe to stay away from her, Long said. Shortly thereafter, Poe came to the uncle's work and "beat him senseless," thus cementing the end of the relationship, according to Long.

"It was like one of his stories," Long said. "It starts with all this hope and happiness and then goes down in flames."

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306 S. High St., Little Italy

Since expanding its Little Italy restaurant 15 years ago, Aldo's has seen more than 400 proposals at its special Romeo and Juliet table. The rectangular cloth table for two, perched on a balcony, was named by owner Aldo Vitale after a suitor walked down to the atrium, got down on one knee and proposed while his girlfriend was still sitting at the table above, according to Margaret Occhiogrosso-Miller, the restaurant's private dinning and event manager.

After that first proposal, word of the table spread. (There's no extra fee for the Romeo and Juliet table; it's available on a first-come, first-served basis.)


The couple sitting at the table is out of view from guests on the first floor while still being able to overlook the entire restaurant, according to Occhiogrosso-Miller. That secluded feeling has been helpful for ensuring that the moment is private, which can be good in the cases of an occasional rejection.

"In that case, that celebratory glass of champagne can easily turn into a shot or glass of scotch at the bar," she said.