Picture of a pagoda in Baltimore

Climb to the top of the pagoda-style observatory at Patterson Park for views of downtown Baltimore.

Photograph by Terry & Belinda Kilby

By Katie Knorovsky

A Civil War-era cannon points its barrel at the Baltimore Harbor from Federal Hill Park, above a sentinel of waterfront luxury condos. Yet the real eye-catcher stands between—a three-story kaleidoscope of glass shards spackled onto the American Visionary Art Museum, an exuberant haven for self-taught artists. Such microcosms play out all around this Maryland port, where centuries of history loom large and a newly buoyant tax base adds gloss, while a mosaic of colorful neighborhoods, vibrant art and music scenes, and a deep-rooted sports culture still shines through. “Baltimore tends to be an informal town that can make fun of itself,” says local arts advocate Megan Hamilton. “There’s an authenticity here that people appreciate.”

Day One

Morning: Step into the Gilded Age

Before Old Bay Seasoning and Michael Phelps’s Olympic records, another Baltimore contribution changed America: the steam-powered locomotive. To glimpse how the rail rush shaped the city—and filled the coffers of the elite—head to Mount Vernon, populated with the grand town houses of Gilded Age industrialists and the free institutions they gave the city, such as the palazzo-style Walters Art Museum, with a 17th-century cabinet of curiosities, and the Peabody Library, with tiered ironwork and preserved tomes under a latticed skylight. Farther north, tree-lined Charles Village leads to the Evergreen House, the “country” estate of the Garrett family railroad dynasty. A guided tour of the pale yellow mansion reveals rare Tiffany lamps, a Leon Bakst-designed theater with Russian folk stencils, and telling relics such as an opulent opium bed. The Edgar Degas and Diego Rivera paintings in the home serve as appetizers for the free Baltimore Museum of Art, with the modern-art anthology of Claribel and Etta Cone (500 Matisses, 114 Picassos, and thousands of others) that hung in the sisters’ Baltimore apartments in the early 20th century. Andy Warhol’s monumental “Last Supper” print holds the spotlight in the new $24.5 million Contemporary Wing.

Afternoon: Meet the Hons

Baltimore thrives on the tightrope walk between highbrow and lowbrow, so balance your cultured morning with the kitsch klatch of Hampden, where the beehive hairdos of brassy 1960s diner waitresses—aka “hons”—endure thanks to native filmmaker John Waters (Hairspray, Pink Flamingos). These days businesswoman Denise Whiting has taken up the charge at her retro Café Hon—going so far as to trademark “hon,” only to give the term back after months of hate mail. For an over-the-top lunch without the controversy, Golden West Café serves Elvis Pancakes any hour, piled with bananas and stuffed with bacon. Tucked among vintage and antiques emporiums along “the Avenue” (actually 36th Street), Sixteen Tons sells sea-mineral aftershave and men’s selvaged denim inside a 19th-century bank building, and Atomic Books stocks graphic zines and Iggy Pop bobbleheads. A world apart, the rehabbed Clipper Mill and Union Mill are worth detouring down the hill for Japanese cold-brewed iced coffee at Artifact and blown glass from a Dale Chihuly protégé at Corradetti studio and gallery.

Evening: Creative Commons

If Mount Vernon says 19th century and Hampden smacks of the 1960s, the story of today’s Baltimore unfolds in Highlandtown, an immigrant neighborhood of Formstone row houses huddled east of Patterson Parks restored 1890 pagoda (its spiraling staircase open to climb Sunday afternoons through October). “Highlandtown is classic Baltimore—white marble stoops and painted window screens [a local folk-art tradition], great ethnic restaurants, and an old-fashioned shopping stretch,” says Megan Hamilton, co-founder of the Creative Alliance, operating out of the neon-marqueed Patterson Theater, built in 1910, which stages everything from burlesque to serious jazz. No matter the billing, expect a convivial crowd lingering in the glow of the mural—a swirl of orange and red—at the on-site Marquee Lounge for its bistro menu (wasabi edamame, beer-braised pork belly).

Day Two

Morning: The Feminine Mystique

Oprah got her break as a Baltimore news anchor in the 1970s—merely one in a line of powerful women to use the city as a launchpad. A quiet edge of Little Italy, east of the Inner Harbor, testifies to three other history makers. Down the block from an alfresco bocce court and hydrants striped red, white, and green is a sign for “Via Nancy D’Alesandro Pelosi.” The speaker of the House grew up on Albemarle Street as the mayor’s daughter and surely developed her famed sweet tooth at old-world bakeries such as Vaccaro’s, where you can zip up your day with espresso and cannoli. Nearby stands the modest brick colonial where Mary Pickersgill stitched the 15-star flag that, after flying over Baltimore’s Fort McHenry in 1814, inspired Francis Scott Key to compose his ode to the “star-spangled banner.” The original flag is preserved at the Smithsonian in Washington, D.C., but here a glass remix sparkles in the sun, fronting the interpretive Star-Spangled Banner Flag House. Next door, the Reginald F. Lewis Museum honors Maryland native Harriet Tubman’s legacy (and the 100th anniversary of her death) with contemporary photos and art by Underground Railroad descendants (through June 23).

Afternoon: Water World

Once second to Ellis Island in port arrivals, Baltimore’s harbor front has anchored the city since the 1700s, bringing in a heady blend—bawdy sailors and prostitutes, Frederick Douglass and Edgar Allan Poe, and, now, rowdy pubgoers and joggers on the seven-mile Harbor Promenade. The harbor offers endless places to lunch on the Maryland blue crab, with Duda’s Tavern in Fells Point serving one of the best crab cakes (no filler). A cheap pint of National Bohemian (“Natty Boh”) is the classic pairing, but unlike the winking Mr. Boh, Resurrection ale and Heavy Seas Loose Cannon are actually brewed nearby. Walk off lunch along shop-lined Thames and Broadway and on to Harbor East, an upscale retail enclave radiating around a gold-flamed memorial to Polish victims of World War II. Chain stores and a Four Seasons have recently moved in, but local standbys include jewel-box Amaryllis and wine boutique Bin 604. Follow the Harbor Promenade west toward the Inner Harbor, a riot of attractions ranging from dragon-shaped rental paddleboats and an armada of tall ships—including the 1854 U.S.S. Constellation—to the shark-finned National Aquarium and Harborplace, a complex of shopping and dining pavilions. Cool off by the “dancing” water fountain on the harbor’s west side, not far from the Orioles’ retro ballpark that spawned a generation of imitations, Camden Yards, or join commuters aboard a blue-and-white water taxi.

Evening: Local Sparklers

Before the sun begins to set, vie for a spot on the terrace of Waterfront Kitchen, a relative newcomer on the tip of Thames Street, jutting into the harbor. Its upmarket “seed to plate” menu highlights Maryland watercress and Chesapeake Bay rockfish, but the view of the red-neon Domino Sugars sign is the true toast of the house. Or water-taxi across the harbor to the Rusty Scupper stop near the glittering American Visionary Art Museum for its top-floor restaurant, Mr. Rain’s Fun House. From there, continue your culture quest for some drama downtown at Center Stage—now celebrating 50 years—to the city’s latest designated arts district, Westside, with the new Everyman Theatre in the shadow of the century-old, crenellated Bromo Seltzer clock tower.

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