Carroll Gardens Branch, May 16, 1923. Originally called the Carroll Park Branch (it was renamed in 1973), the Carroll Gardens Library was completed in March of 1905. Deigned by William Tubby, a well-known Brooklyn architect better known for his Romanesque and Dutch Revival-style private residences, the library structure is a more modest Classical Revival building. The facility served the considerable Italian-American community of the neighborhood, providing lectures in Italian on Sunday in the decade after it opened. In the 1930s the library offered citizenship classes and worked with National League of American Citizenship assisting more than 10,000 people in the naturalization process.

Sacred Hearts of Jesus and Mary and St. Stephen Roman Catholic Church, 1951. According to the history of the church, "At 3:00 p.m. on the crisp Wednesday afternoon of January 10, 1951, the clock in the tower of what was now known as Sacred Hearts & St. Stephen’s Church rang only twice instead of the usual three times." A five-alarm fire, which started in the choir loft, burned through the church, collapsing the roof and destabilizing the tall steeple. The fire destroyed many of the stained glass windows, the new $20,000 organ, and all of the vestments. Thankfully no one was killed, but the damage was estimated at $2 million. The church rebuilt with donations from parishioners and the generosity of local Jewish and Protestant congregations. St. Stephen's was founded in 1866 in a former Episcopal Church at Carroll and Hicks Streets. The church building seen here was erected in 1875 and designed by famed Catholic church architect Patrick Keeley. Its high steeple cross, illuminated at night, served as a beacon for sailors entering New York Harbor. The Sacred Hearts of Jesus and Mary was established in 1882, the first Italian parish on Long Island. It first used space in a church at Warren and Hicks Streets. The parishes merged in 1941 when Robert Moses' BQE plans forced the razing of the Sacred Heart Church (as well as two other early Italian parishes nearby). The combined parish remains a vibrant part of the Carroll Gardens community. Its annual Good Friday procession is one of the oldest and most well known in the diocese.

Defonte’s Sandwich Shop, 1939. Founded in 1922 by Nick Defonte, the sandwich shop claims to be the oldest eatery in Red Hook.

Construction was begun on the Brooklyn-Battery Tunnel in 1940. Initially, Robert Moses had pushed for a bridge in the same place, but those plans were scrapped by the Dept. of War citing both security concerns (the bridge would be close to Brooklyn's Navy Yard) and citizen's outcry to preserve the Battery, which was largely undeveloped at the time (an unstated reason was Moses' feud with President Roosevelt.) Instead of a bridge, a tunnel was built to connect the two boroughs. Four towers ventilate the two-mile-long strip of underground highway, refreshing air every 90-seconds.

South Congregational Church, 1922. The South Congregational Church complex at Court and President Streets includes a chapel (1851), the main church (1857), the ladies parlor (1889), and the rectory (1893). According to its 1982 Landmarks Preservation Commission report, the church “fits into a general pattern of towered Early Romanesque Revival style churches, but is unusual for the extraordinary manner in which the brick is modeled on the facade.” The church steeple, pictured here in 1922, was a perennial concern. A 1879 Brooklyn Daily Eagle report observed that “the steeple has always been more or less regarded as insecure” after January winds made “the entire tower rock from side to side.” In 1902, the Buildings Department declared the spire “unsafe” and mandated repairs. The steeple survived until at least 1936, when the Eagle reported that the church had decided to keep the “source of pride and worry.” However, it was dismantled prior to the church’s 1982 Landmark designation and its subsequent conversion into residential apartments.

The name Cobble Hill came into use in the 1950s, likely an update from the name "Cobles Hill" which can be found on a 1766 map. Organized community groups fought against large housing projects, and advocated to make the area an historic district.

The Seamen’s Goodwill Mission of the Brooklyn Church and Mission Federation, 1937. Blocks away from the wharves of the Atlantic Basin, neighborhood institutions suited the working class waterfront community. It was described in list of Brooklyn charitable organizations as, "a comfortable building houses hundreds of homeless and friendless seamen every year and furnishes food and shelter to many thousands of men who would seek friendships in the speakeasies of that section. It has been a life-saving station for tens of thousands of men during the years of the past."

Brooklyn approach to the Brooklyn-Battery Tunnel, 1950. Conceived in the late 1930s by city officials, this project was one that master planner Robert Moses was actually not a proponent (and complained about the resulting tunnel for decades). Moses wanted to construct a bridge between lower Manhattan and Brooklyn but city officials, including Mayor LaGuardia, and President Roosevelt advocated for the tunnel (with FDR citing issues of national security in the construction of a bridge as well as his dislike for Moses). Construction on the tunnel began in 1940, with FDR attending the groundbreaking ceremony, but was waylaid by World War II. Completed and opened to traffic in 1950 it is the longest continuous underwater road in North America. In 2010 it was renamed (officially, though not colloquially) the Hugh L. Carey Tunnel, for the former New York State Governor.

“Hamilton Avenue north from Summit Street. Many of the buildings on the east side (right) of the avenue were later razed to make way for the construction of Gowanus Parkway. October 21, 1939.” Construction on the Gowanus Parkway (later the Gowanus Expressway) began in 1939, but it was the construction of the Brooklyn-Battery Tunnel entrance via Hamilton Avenue that saw the demolition of much of this neighborhood; every building pictured was torn down. At right is the intersection of Carroll and Van Brunt Streets. The triangular building at left is no. 100. In the background at left is the India Wharf Warehouse, at Conover Street. The block-long building sat between Hamilton Avenue and the India Wharf frontage of the Atlantic Basin. It was formerly home to the India Wharf Brewery.

St. Paul’s Protestant Episcopal Church, 1922. The High Victorian Gothic church was designed by architect Richard Upjohn, who lived just a few blocks north at the corner of Clinton and Baltic Streets. The church was completed in 1884, 17 years after construction commenced.

St. Paul’s Episcopal Church and Female Orphan Asylum. July 4, 1930. Note the American flag hanging from the rectory window, to the left of the church building.

In 1878, the cornerstone was laid for the Pilgrim Chapel on the corner of Henry and Degraw Streets. The architect, J. Cleveland Cady, designed an Italianate-style building with a tall tower that had an exterior of Philadelphia pressed brick trimmed with Belleville stone and terra cotta. The auditorium had a high ceiling with open timbers, and was lighted by a continuous clear-story in which were windows filled with rolled cathedral glass of beautiful designs. There were 15 rooms grouped around the auditorium, all having direct light, ventilation and heat. When the Sunday-school rooms were opened into the auditorium, there was a capacity of 1,200 people.

Bakery at the corner of Henry and President Streets, June 26, 1961. This late 19th century corner building draws architectural elements from the Romanesque Revival (rough-hewn stone, round-arched upper windows) and Queen Anne (asymmetry, tiled roof) styles. The corner tower and pressed metal cornice along the entire roofline include intricate detail.

The completion of the Brooklyn-Battery Tunnel in May, 1950 marked the end of 10 years of planning and engineering, overcoming back-breaking labor, war, and financial difficulty that stood in its way. At the time the nation’s longest most modern underwater vehicular tunnel, the Brooklyn-Battery tunnel had about as turbulent a history as any of New York’s infrastructure. It was the most expensive two-mile bit of highway ever built at the time - costing more than $40,000,000 a mile. A connection between Brooklyn and Manhattan was first conceived of in 1929. Initially, a graceful, double-unit suspension bridge was to connect the boroughs, featuring a ramp leading down to Governor's Island at the apex. Unfortunately, various groups objected against its potential to disfigure the Battery Park Landscape, and President FDR cited security concerns. In the end, the War Department barred the construction of the bridge in 1939. Funding dwindled on the endeavor to drill a two-mile tunnel between Battery Park and Brooklyn until the Reconstruction Finance Corporation offered $57,000,000 in loans towards its construction. Ground broke on October 28th, 1490, with President Franklin D. Roosevelt on hand for the momentous occasion. Major construction work began in 1941 and for nearly two years, it slowly marched forward. On the Manhattan end, a hole 24-feet in diameter was carved through solid rock which began 2,800 feet under the surface of the river. The Brooklyn side was challenged with softer rock to drill through at about 1,000 feet from the entrance at Hamilton Avenue and Van Brunt Street. The United States entry into World War II put an end to construction on the tunnel, leaving both materials and manpower becoming scarcer every day. In fact, progress on the tunnel came to a standstill towards the end of 1942. For three years the whole project lay idle, only the throne of pumps on the Brooklyn side signifying that the tunnel job was not forgotten. Things began humming again at the end of the war in 1945. Water was pumped out, concrete shields were removed, and men came back to work. It took another five years for the tunnel to be completed and acclaimed as a modern marvel. Fully illuminated, with fresh air exchanged every 90 seconds, the tunnel was opened with great fanfare.

By 1916, the Pilgrim Chapel had been decommissioned and was known as the Oriole Theater. Today's it's a MET supermarket.

36 Strong Place, 1958. In 1834, Cobble Hill's current street grid was laid out between Atlantic Avenue and Butler Street (later Harrison Street, now Kane Street). Strong Place was the first new street paved below that boundary, in 1856. Sitting at the back of its lot, no. 36 was likely a stable belonging to the broker Charles Kelsey, who owned several lots on or near Strong Place and developed properties in the surrounding area.

J.H.S. 142, Stranahan Junior High School, June 26, 1961. J.H.S. 142, the junior high school attached to P.S. 142, occupied a mid-century addition at the corner of Henry and Coles Streets (note the 1959 cornerstone). The school closed in 2006.