The Gothic Revival Main Entrance Arch and clocktower were designed by the firm of ecclesiastical architect Richard Upjohn and son Richard M. Upjohn—both Brooklyn residents, later interred at Green-Wood—and completed in 1865. As described the Landmarks Preservation Commission's 1966 Designation Report, the Upjohn-designed entrance "represents an ingenious linking together and piling up of architectural elements to create an impressive main gateway to the cemetery." Green-Wood's gates are also home to an unexpected population of cemetery guests: a colony of monk parakeets, allegedly escapees from an illicit shipment to Idlewild Airport (JFK).

DeWitt Clinton, a United States Senator, governor, and mayor, and the visionary behind the Erie Canal, was at one time the most revered New Yorker. Having died in 1828, Clinton was originally interred in Little Albany Cemetery. Green-Wood, however, in an attempt to attract publicity to the newly-established cemetery, made arrangements to have Clinton reinterred, with a heroic bronze monument marking his grave. The statue of Clinton is by sculptor Henry Kirke Brown, and the bas reliefs that adorn the monument base were designed by Richard Upjohn. It was unveiled, with much fanfare, in 1853.

Receiving tombs were a staple in nineteenth-century cemeteries, serving as a holding space for caskets until they were ready for interment. They were especially important during the cold winter months when the frozen ground made digging impossible. This Receiving Tomb designed by Richard Upjohn was the temporary resting place of many of Green-Wood's residents.

The chapel was constructed in 1911 after designs by Warren and Wetmore, architects of Grand Central Terminal, and is a reduced replica of Christopher Wren’s Thomas Tower at Christ Church College in Oxford, England.

Arbor water was one of several glacial ponds on the land that would become Green-Wood. It was filled in 1911 to make space for Green-Wood's Historic Chapel, designed by architects Warren & Wetmore and completed in 1912. As seen in this photo, rowboats were once available for cemetery visitors to take out on the water.

Dating to the early 1870's, the Matthews monument was created by prolific sculptor Karl Muller. Executed in terra-cotta and marble for the great sum of $30,000, it was named the "Mortuary Monument of the Year" when it was unveiled. The Mathews monument is adorned with the likenesses of members of the Matthews family, including John Matthews laying atop a sarcophagus at the center, and the faces of his daughters atop the four columns. The statue seated at the second level, which has greatly deteriorated over the years, typifies grief. Various flora and fauna can be found throughout the monument, as well as four gargoyles on the corners which spit water when it rains. The spectacular monument was once even more elaborate, featuring a central spire that loosened and has since been removed.

The Arctic Monument, standing at the center of the Brown family lot, was commissioned by James Brown (1791-1877), head of the powerful Brown Brothers banking firm, to honor those lost in the sinking of the steamship Arctic. When the Arctic went down in 1854, James Brown lost a number of family members: his son William Benedict Brown, William’s wife Clara Moulton Brown, their infant daughter Grace, his daughter Maria, his daughter Grace, and her son Herbert. Their names are carved into the front of the monument. Sculpted by artist John Moffitt, the marble monument features at its center a likeness of the sinking Arctic. Though the ship’s mast and sails have been lost over time, the monument’s stone canopy has protected much of the ship’s detailing from the elements. Look up above the ship at the detailed carving by Moffitt.

Greeley's monument was erected by America's printers. Topped with a bronze bust of him by Charles Calverley, the pedestal has a bronze bas-relief on one side which shows Greeley as a youth, with composing stick in hand, standing over his type case. Another panel depicts a plow, an apparent allusion to Greeley's famous recommendation to the unemployed during the panic of 1837, "Go West, young man, and grow with the country." Greeley wrote his own epitaph, "Fame is a vapor; popularity an accident; riches take wings; the only earthly certainty is oblivion; no man can foresee what a day will bring forth; while those who cheer today will often curse tomorrow; and yet I cherish the hope that the journal I projected and established will live and flourish long after I have mouldered into forgotten dust.. and that the stone which covers my ashes may bear to future eyes the still intelligible inscription, Founder of The New York Tribune."

The son of Theodore Ledyard Cuyler and Annie E. Cuyler, George Sidney Cuyler died at the age of four from scarlet fever, leaving behind a twin brother, Theodore, and two heartbroken parents. Theodore Ledyard Cuyler (1822-1909) was the longtime pastor of Brooklyn's Lafayette Avenue Presbyterian Church and nationally known for his work in both the temperance and abolitionist movements. Cuyler employed noted sculptor Charles Calverley to create a likeness of young Georgie to adorn his monument. The marble relief cameo, protected from the elements behind glass, remains in fine condition.

Erected by a committee for the volunteer firemen of New York City, the Firemen's Monument memorializes two firemen, Engineer George Kerr (1816-1848) and Assistant Foremen Henry Fargis (-1848), who died fighting a fire on April 2, 1848. The monument, rich in fire-related symbolism, was sculpted by Robert E. Launitz. Standing almost 24 feet high, the monument is topped with a statue of a fireman, wearing a hero’s laurel wreath, saving a child. It is adorned with the coat of arms of New York City, hydrants, hoses, speaking trumpets, hats, down-turned firemen's parade torches, hooks, and ladders.

Samuel F. B. Morse, perhaps best known for the invention of the telegraph and development of Morse Code, was also a leading painter, serving as the first president of the National Academy of Design. After Morse's wife fell ill and died before he could reach her, Morse turned his attention to developing a faster means of communication - what would become the electromagnetic telegraph—the first practical system for communicating faster than a person could carry a note. Morse's monument at Green-Wood stands prominently atop a hill overlooking Crescent Water.

Piano maker Henry Engelhard Steinway (1797-1871) migrated to New York City from Germany in 1851. By 1860, his company, Steinway & Sons, had already become the leading piano manufacturer in the country. The business stayed in the family for many years and continued to find great success. The Steinway Mausoleum at Green-Wood, built in the 1870s at a cost of $80,000 (equivalent to over $1.5 million today) is the cemetery's largest, with room for between 150 and 200 interments. It was designed by sculptor and funerary architect John Moffitt.

Once the finest monument in Green-Wood, the monument to Charlotte Canda (1828-1845) memorializes a young girl who died a tragic death in a carriage accident on the night of her seventeenth birthday. The basic design of Charlotte’s monument was sketched by her as a memorial to her recently deceased aunt. After Charlotte’s death, her father adapted to sketch to memorialize his daughter, including elements such as the books, musical and drawing instruments that she was so fond of, and the parrots that were her constant companions. Charlotte’s effigy appears in the niche, with a star above it, symbolizing immortal life. A butterfly with wings extended is emblematic of her liberated spirit. To commemorate Charlotte’s age at death, 17 rose buds, symbolic of a female life cut short, make up the wreath around her head; the monument is 17 feet high and 17 feet deep. Long lost from exposure to the elements, Canda’s epitaph once read: “So sinks from sight Eve’s golden star / Lost in the watery depths afar/ Yet still does the fair planet burn / Not hopeless is our Charlotte’s urn / In God’s own morn her orb will rise / Once more – a star of Paradise.”

Green-Wood's Civil War Soldiers' Monument honors the 148,000 New York men who fought "in aid of the war for the preservation of the Union and the Constitution." Construction of the monument began just four years after the end of the Civil War and it was dedicated in 1876. The monument features four life-sized statues of soldiers, representing the four branches of the Army: engineers, infantry, artillery, and cavalry. Originally cast in zinc, the sculptures had deteriorated badly over the years and were replaced in 2002 with reproduction bronzes.