1. Walk west on Montague from Court St. and Cadmen Plaza. Lining the plaza are the New York Supreme Court Building, the Victorian Romanesque General Post Office (and a statue of Henry Ward Beecher), and Borough Hall, which was Brooklyn’s City Hall until the borough was consolidated into New York City in 1898.
2. At the corner of Clinton St. and Montague you’ll find the 1847 Gothic Revival St. Ann and the Holy Trinity Church. It has a stunning interior of intricate sculpture and stained glass windows by William Jay Bolton (making it the first major installation in America). In addition to worship services, St. Ann’s also has concerts and performances. Turn right and go up to Pierrepont.
3. At the corner of Clinton Street is the Brooklyn Historical Society, home to permanent and changing exhibits and an extensive library focused on Brooklyn and New York. The 1880 building has impressive interiors, and its façade includes terra cotta sculptures of a Viking and Native American over the entrance, as well as busts of Columbus and Ben Franklin higher up.
4. Walk four blocks west, past beautiful 19th-century homes in a variety of styles. At the intersection with Monroe Place, you’ll find the imposing New York State Supreme Court, Appellate Division (seemingly out of place in this residential neighborhood!) and the 1844 Gothic Revival First Unitarian Church. The Brooklyn Chamber Music Society performs here (an excellent way to see the church’s Tiffany stained glass windows!). Number 106 has a unique Art Nouveau style, with stained glass over its bay windows and front door. Notable is the 1890 Herman Behr House (at the corner of Henry St.), with its bays, turrets, and terra cotta sculptures. It later became a hotel, apartment house, and even a brothel run by Xavier Hollander (also known as the “Happy Hooker”!).
5. Head to the Brooklyn Promenade (or Esplanade) for fantastic views of the Manhattan skyline and the Brooklyn Bridge. The sound of traffic can be heard from the Brooklyn-Queens Expressway, which runs beneath the Promenade.
6. Backtrack a block and turn left/north on Willow street. The long block of Willow between Clark and Pierrepont Streets also features several notable homes. Look for the skylight in the pavement before #157, which once lit a tunnel leading from #159 to a stable. #151, a former carriage house converted into a luxury home; and the Federal-style row houses at #155-159; #108-112, ornate Queen Anne buildings with flamboyant terra cotta decoration; #102, the Danish Seaman’s Church (a remnant of the area’s busy waterfront. 70 Willow St., meanwhile, was once Truman Capote’s home; it’s here that the author wrote Breakfast at Tiffany’s and In Cold Blood. In fact, the neighborhood has been home to many great writers, including Arthur Miller, W. H. Auden, Thomas Wolf, Carson McCullers, and Norman Mailer. This house recently sold for a record $12 million (a bargain considering the original asking price: $18 million!). The “modern” building on the southwest corner is a Kingdom Hall of the Jehovah’s Witnesses, one of 30 buildings the group owns in Brooklyn Heights.
7. Turn right on Orange Street and walk a block and a half east to #57, Plymouth Church(1849). This historic church was known as the “Grand Central Depot of the Underground Railroad” for the many escaped slaves it sheltered—but it was made famous by its dramatic abolitionist preacher, Henry Ward Beecher. Among those who came to hear Beecher were Mark Twain, Booker T. Washington, and Abraham Lincoln. In fact, so many flocked to hear his sermons that special “Beecher boats” were needed to ferry the throngs from Manhattan!In contrast to the church’s simple, barn-like exterior, its interior is laid out in a theater style (designed by Beecher himself) and features remarkable stained-glass windows (some by Tiffany) and a piece of Plymouth Rock. In the adjoining garden, you can see a statue of Beecher and a relief of Lincoln.
8. Return to Willow and continue North. As you continue down Willow, note the plaques on #45 (dated to 1820) and #57 (1825). At the northeast corner of Cranberry and Willow is 19 Cranberry St, home of the Castorini family in the 1987 film Moonstruck. Many of the film’s exterior shots were filmed here, including Cher’s wistful stroll down this block kicking a can. Continue north on Willow Street (the street numbers will increase) and notice #37, one of the nation’s first apartment buildings.
9. Turn right onto Middagh Street. This block of Middagh Street between Willow and Hicks holds some of the oldest homes in the city, dating back to the founding of Brooklyn Heights. Numbers 31-33 were built in 1820 and served as a “men’s hairdressing parlor” and paint store, while the clapboard house at #30 dates to 1824. Built in 1820, the Federal-style house at #24 is believed to be the oldest house in the neighborhood.
10. Track back to Columbia Heights/Everit. Turn right and walk down the hill and under the bridge connecting two large yellow buildings. At the top of this former factory, you’ll see the words, “Watchtower,” indicating it is the Jehovah’s Witnesses’ headquarters.
11. Turn left on Fulton Street. The redbrick fortress before you is the Eagle Warehouse and Storage, once the site of The Brooklyn Eagle, the newspaper edited by Walt Whitman from 1846-1848. Whitman lived nearby, and his Leaves of Grass was first printed a few blocks from here.
Under the bridge is the famed River Cafe. Continuing north is more waterfront park, plus the trendy neighborhood of DUMBO, where old warehouses and factories have been converted into art galleries, performance spaces, apartments, shops, and restaurants. Wander down Front Street to Manhattan Bridge and back.
Fulton Ferry Landing. Ferries to Manhattan have operated here since 1642, and this is where Robert Fulton’s steam ferry began connections in 1814, leading to the growth of Brooklyn Heights as a residential enclave. It was also here, in 1776, that George Washington smuggled his defeated troops across the river under cover of night and fog… saving them, and the nation, from conquest by the British Army.