Baltimore dates to 1729, but the city—the country’s second-best for minority-owned businesses, according to Forbes—is a long way from feeling old and stuffy. Evidence of the past is everywhere—such as Edgar Allan Poe’s grave site downtown—and pop history offers additional fodder for fun. On Dallas Street, I used to stop in at the world’s coolest Airbnb, featuring a chandelier used in John Waters’ Polyester. The “Palace on Dallas” is now gone, but Baltimore is still a long embrace of pleasure and possibility.
The Ivy Hotel
A Relais & Châteaux property, The Ivy is a 17-room affair set in a former 1889 mansion built by banker John Gilman and designed by Charles Carson. The Ivy is a profoundly elegant hotel, with—of course—garlands of ivy, 23 fireplaces, and acres of green marble and carved wainscoting. The experience is akin to stepping into the 19th century.
American Visionary Art Museum
AVAM is both an internationally recognized outsider-art museum and a beloved generator of joy, known for its annual Kinetic Sculpture Race with fantastic human-powered art creations. AVAM’s exhibitions knock visitors over with whimsy and intelligence, and the collection includes wonders such as Vollis Simpson’s 55-foot-tall Whirligig.
George Peabody Library
In 1857, George Peabody founded the Peabody Institute as a gift to repay the citizens of Baltimore for their hospitality. The George Peabody Library, opened in 1878 and designed by local architect Edmund G. Lind, incorporates 300,000 volumes and five open tiers of ornate cast-iron balconies. This remains one of the most beautiful library spaces in the world.
The Walters Art Museum
Established in 1934 with the bounty of philanthropist Henry Walters, the institution features 36,000 objects spanning seven millennia, including Ethiopian icons and Roman sarcophagi. The exhibition “Selections From the 19th-Century European and North American Collection” includes such gems as Child With Strawberries by Black American artist Joshua Johnson.
Gertrude’s Chesapeake Kitchen
Set within the Baltimore Museum of Art, Gertrude’s is known for a high-Baltimore menu with everything from Chincoteague single-fry oysters to crab cakes. The restaurant overlooks an idyllic sculpture garden featuring pieces by Alexander Calder and Auguste Rodin. During the museum’s summer jazz series, Gertrude’s offers a Jazz + Dinner experience.