Stunning Then and Now Photos of Staten Island that Show How Times Have Transformed

The essence of a place is not only defined by its current panorama but also by its storied past. As we traverse through decades of images, “Then and Now” photos of Staten Island offer a unique portal through which we can experience the island’s evolution. These paired images, some a century apart, capture the changing face of Staten Island while celebrating the enduring spirit of its community.

Peering into the paired photographs, certain streets, once bustling with vintage vehicles and pedestrians in period attire, are now lined with contemporary cars and city dwellers donning modern fashion. Yet, the foundational architecture, the heart of the street, remains, echoing tales of yesteryears and whispering secrets of today.

The island’s green spaces, some of which have flourished for over a century, have their own stories to tell. In some spots, dense groves from decades ago have made way for urban expansion. In contrast, other areas depict nature’s tenacity, with the same trees standing tall, only now surrounded by newer benches or playground equipment.

Certain landmarks, like bridges, have become symbols of Staten Island’s identity. The paired images reveal their enduring majesty, even as the surroundings have transformed. Similarly, waterfronts, once hubs for trade and transport, now serve as recreational spots, with the essence of water acting as a continual, soothing presence.

Perhaps the most touching pairs are those capturing everyday life. Children playing, vendors selling, and families gathering—some scenes remain touchingly similar despite the decade’s gap. The setting might have changed, but the spirit, the joy, the camaraderie, resonates across time.

#1 Market at Targee and Van Duzer Streets, Stapleton, photographed on January 4, 1949. Second photo is from 2020

#2 Hart Boulevard transformed from wooded land into a developed area; 1900s – 2009

#4 Silver Lake Park in Two Different April Scenes, 1982 and 2019

#5 Soldiers march on Amboy Road near Richmond Road in New Dorp, captured on October 26, 1912. Second photo is from 2019

#6 Hillside Terrace in Great Kills offers a glimpse into its undeclared history.

#7 Buffalo Street, Bay Terrace, looking east, circa 1939 and the street east of the SIR today.

#8 The Boulevard in 1899. Notable for its University Temple, a large auditorium.

#9 Main Street, Tottenville: A view of the street, date unknown.

#10 70 Beach Street in Stapleton was originally the Liberty Theatre in 1918. Now houses various businesses.

#11 This home at 3525 Victory Blvd.

This Home At 3525 Victory Blvd.

It was where Ichabod Crane a career military officer for 48 years and the probable namesake of the protagonist in Washington Irving's "The Legend of Sleepy Hollow" lived. Crane died on Staten Island in 1857. His family lived here from 1854 to the late 1800s in a house located on Richmond Turnpike, now known as Victory Boulevard. The house at 3525 Victory Blvd. was demolished in March 1989 when preservationists were unable to raise the money to move it to the Historic Richmond Town. Commercial buildings now occupy the site

#12 Empire Theater on Richmond Terrace, closed in 1978, now Rescue Ministries.

#13 One of the oldest Staten Island photography studios was Weitzman’s Photo Shop, which opened in 1872 at 61 Canal St., Stapleton.

One Of The Oldest Staten Island Photography Studios Was Weitzman’s Photo Shop, Which Opened In 1872 At 61 Canal St., Stapleton.

Shop is now the Sri Lankan & Cultural Museum of NY

#15 Shops are shown along Port Richmond Avenue in Port Richmond, circa 1940’s. The Avenue today as new stores have taken the place of the 1940s shops.

#16 Skippy’s truck, founded over 50 years ago; Dawn Bellach took over in 1984.

#17 A & E flying service in 1960s and the same place in 2017

#18 Charles R. Wittemann’s airplane plant near Manor Rd., Castleton Corners, opened in 1905 and later moved to New Jersey. Second photo is from 2015

#19 Engine 159 firehouse at 1592 Richmond Rd., Dongan Hills, constructed in 1930.

#20 John and Rose Tinessa’s Store at 522 Port Richmond Ave., Now Part of Denino’s Brick Building, 1930s – 2015

#21 Social Events, Weddings, Political Rallies, and Bowling at The Columbian Lyceum, Then and Now.

#22 The Amber Club was located at 6389 Amboy Rd. it’s now a funeral home.

#24 Corner of Forest and Davis avenues, a popular eatery since 1977.

#25 Marvin Golden’s Deli in New Springville featured a 1930s subway car. Closed in 2012.

#26 Great Kills Yacht Club Staten Island. 1900s – 2018

#27 St. James Hotel: Built in 1795 as a private residence, it became a hotel with several name changes. Its most famous guest was Aaron Burr.

#28 St. Mark’s Apartments and Hotel Castleton in St. George. Now the Castleton Park Apartments.

#29 Port Richmond Farmers Market was located at 1851 Richmond Terrace, 1965.

#30 St. Luke’s Church, circa 1930, now operates as Big Nose Kates.

#31 Jewett Avenue Views: Comparison of the street from College Avenue between the late 1800s and today.

#32 Messina’s Market, a long-standing family grocery, moved for the Paramount Theater in 1930.

#33 Horton’s Row on Westervelt Avenue in New Brighton, built around 1880, granted New York City landmark status.

#34 Bowling on the Green: Once located on Mill Road, it was torn down in 2004 to make room for townhouses.

#35 Amboy Road, Annadale, where children are seen playing in a lot between Barclay and Arden Avenues around 1924.

#36 Closing of Tirone’s Shoe Store in 2010 marked an end of an era for 164 Port Richmond Avenue. Second photo is from 2010

#37 The Old Mill Restaurant was a popular venue on Staten Island until a fire in 1957.

#38 Circa 1940s, milk deliveries shift from horse-drawn wagons to trucks at Janssen Dairy on Manor Road near Schmidts Lane. Second photo is from 2014

#39 Johnson Ave. from Craig Ave. in Arthur Kill Rd. offers a historical view.

#40 Intersection of Victory Boulevard and Corson Avenue, captured in 1903.

#41 Tompkinsville Post Office in 1895; uniformed men likely mail carriers. Post Office locations changed over the years.Second photo is from 2011

#43 Plaza Bar and Restaurant: Located at 1177 Castleton Ave, it later became The Plaza Tavern and now hosts Joe Holzka Community Garden.

#44 Streetcars were common in Port Richmond Square in 1920, before cars took over.

#45 Happy Arbor Day! In 1991, a Parks Enforcement police officer patrolled Clove Lakes Park near Royal Oak Road on horseback. Today, in 2022, there are more trees surrounding what looks like the same older tree, which is still standing.

#47 Former mansion on 1600 block of Richmond Avenue, Bulls Head, taken between 1939-1941. A symbol of bygone grandeur.

#48 Hylan Shopping Plaza in 1986; The Boulevard. 2021.

#49 Grasmere traffic sign on Hylan Boulevard just north of Old Town Road in 1937 and bottom is today.

#50 Penneyfeathers was located on New Dorp Lane during the 80s and 90s and later the Paul Mitchell School.

#51 The Ritz Theater in Port Richmond, Once Owned by the Moses Family, Closed in 1968.

#52 Joyce’s Tavern on Richmond Avenue in Eltingville remains a popular spot since 1966.

#53 Rossville Post Office around 1880. Closed in 1919, it was located at 2574 Arthur Kill Road.

#54 Buel Avenue in Dongan Hills, showing a railroad crossing built in the early 1900s.

#55 Fruit and vegetable stand at Forest and Union Avenues, Mariners Harbor, around 1973.

#57 Harbor Lights Bar, Later Became New Life Fellowship Christian Church, 1980s. And 2019

#58 Residential Construction in Oakwood, Yellow Street Signs, 1973.

#59 Workers’ housing on Kreischer Street, Kreischerville, taken on May 3, 1937; name later changed post-WWI.

#60 Tinessa’s Italian-American grocery and meat market in Port Richmond, 1930s-1940s.

#61 Late Borough President Albert V. Maniscalco at the Opening of John Piazza’s Butcher Shop, Piazza’s Market, 1950s

#62 Max Geldner’s New Dorp Hotel was a popular gathering place on Richmond Road.

#63 The Arrochar Inn After a Winter Storm, 1947. And the same place in 2020

#64 National City Bank Building, Still a Bank Today, 1949.

#65 The Staten Island Airport on Richmond Avenue was operational from 1941-1965.

#66 Brighton Heights Reformed Church, St. George, rebuilt after accidental fire destroyed the original building, 1996.

#67 The fruit stand on Forest Avenue and Union Street in Mariners Harbor, 1973 and the same spot in 2019

#68 Comparison of Targee Street and Vanderbilt Avenue in Stapleton from 1937 and 2019.

#70 Sureyya Celiker has shoes in hand as she wades across Victory Boulevard at Bradley Avenue, Castleton Corners, on her way to work. Schaffer’s Tavern is in the background in 1980. Second photo was taken in 2021, Shaffer’s is replaced by Victory Bank

#71 Work on a $4 Million Sewer Project in Dongan Hills, March 1988.

#72 Masonic Temples across Staten Island – The buildings that housed the Masons on Staten Island were often multi-purposed or re-purposed

#73 Midway Diner located at 803 Forest Avenue. It is now McDonalds

#74 33 Victory Blvd., then called Richmond Ave., 1940.

#75 Forest view on Bement Avenue in Historic Richmond Town. 1940s – 2009

#76 Rosebank Storage Warehouse, 139 Bay Street, 1940 and 2013

#77 The Victory Diner’s rise and fall, from Castleton Corners to its sad end in Hurricane Sandy.

#78 John and Rose Tinessa’s Store, Port Richmond Ave., Circa 1940s

#79 Staten Island Expressway Construction, Circa 1962, and the Expressway Today

#80 Staff of Leonhard Weinmann’s Bakery, 388 Van Duzer Street, 1918.

#82 The Liberty Theatre, Staten Island’s Most Modern Theater When It Opened, 1918.

#83 Azzara Funeral Home, Sand Lane, South Beach, founded in 1896, one of Staten Island’s oldest funeral homes, 1919.

#84 Fox Hills Golf Club, Turned into Park Hill Apartments; Once Military Housing and Middle-Class Community, Developed in 1965.

#85 Conca D’Oro in Mariners Harbor, Motel with Olympic-Size Pool, Restaurant, Later Homeless Shelter, Closed in Early 1990s

#86 Al Deppe’s Restaurant was a popular eatery at Richmond Avenue and Arthur Kill Road.

#87 The intersection of Richmond Hill Road and Richmond Avenue; the arrow points to a sharp curve at the bottom of the hill at the intersection, 1938.

#88 In May of 1964, the push was on to complete both the bridge and the Staten Island Expressway by the scheduled November 21 dedication; Grymes Hill is on the left

#89 Hylan Blvd looking north from Guyon Ave., circa 1935, and now.

#90 Water Street, Stapleton, with trolley tracks and Washington Park across the street.

#91 Arthur Kill Road near Winant Avenue in Rossville, 1930.

#92 The building that formerly housed the 167-year-old St. Simon’s Episcopal Church in Concord has been demolished by a developer planning to build 19 single-family homes on the site, according to city records.

#93 Located in Pleasant Plains Camp St. Edwards provided summer getaways for thousands of youth; currently, the property is filled with homes, 1948.

#94 The Silver Fox and Angelo’s Pizza Later Play Sports Bar (closed permanently May 2020) and The Pizza Parlor (open for business)

#95 Central Avenue in St. George has gone through many changes over the years, including horse-drawn carriages being replaced by a parking lot, 1916.

#96 Guyon Avenue, Looking South from R. R. Station, Oakwood Heights

#97 Forest Avenue Featuring A&P Grocery Store, DeJong’s Bakery, and Joe Geist’s Liquors, Circa 1940.

#99 Log Cabin Inn on Forest Avenue was famous for its nightly entertainment.

#100 Staten Island University Hospital/ Northwell Health, south campus.Then and Now

#101 Northfield Hotel at Ferry Street and Richmond Terrace, Port Richmond Square.

#102 Main police station at 19 Beach Street, Stapleton, established in 1875; now Eden II.

#103 The Midway Diner located at 803 Forest Avenues at Broadway in West Brighton was one of the last diners to close in the 80s and be replaced by a fast food chain.

#104 Grant City Building: Initially the Atlantic Inn Restaurant, it later became a funeral home and is now a doctor’s office.

#105 Richmond Terrace between York Avenue and Jersey Street

#106 Oakwood Shopping Center Stores, Amboy Road and Clarke Avenue, Staten Island, 1960s.

#107 View of Clove Lake Stables in West Brighton, Sold to a Developer, 1985.

#108 Hunter’s Tavern, 1297 Huguenot Avenue, Huguenot Park, Staten Island, N.Y. [dining area with hearth and dance floor], now is a residential home.

#109 Houghwout’s Store on Richmond Terrace was a staple in 1898.

#110 Dilly Dally Club, Now Kettle Black, Staten Island, Circa 1950s

#111 Shopping on Staten Island before the Mall, before the bridge, meant places like Port Richmond Avenue.

#112 Steel frame of the Staten Island Mall, as seen from Richmond Avenue, August 1972.

#113 Woodrow Road near Alexander Avenue, February 22, 1973.

#114 Volunteer Engine Co. No. 3 outside their firehouse at 232 Richmond Avenue, shortly after moving in 1900.

#115 Victory Boulevard: Renamed after WWI, this street was formerly known as the Richmond Turnpike.

#116 Richmond Engine Company No. 1 at 3664 Richmond Rd. is one of Staten Island’s last volunteer fire companies.

#117 Jefferson Avenue Station in Dongan Hills, circa 1950s.

#118 Thomas Wiberly’s Broadway Café, located at Castleton Avenue and Broadway featured Rubsam & Horrmann beer.

#119 The transition from horse-drawn milk wagons to trucks for door-to-door deliveries at Janssen Dairy on Manor Road near Todt Hill Houses, 1940s.

#120 Located on a stretch of Richmond Terrace, historically known as the Shore Road, was even referred to as “Captains Row,” owing to the numerous ship captains who purchased or built fine homes along the thoroughfare. Home of Capt. Stephen D. Barnes. It stands today on 2876 Richmond Terrace, between Van Pelt and De Hart avenues.

#121 Video rental stores in Staten Island in the 80s, including Victory Home Rentals on Victory and Wescott Blvds., Meiers Corners

#122 Cutting Ice-Silver Lake, stereo photograph, 1880s.

#123 Craig Avenue at Amboy Road on Staten Island hasn’t changed much since 1956.

#124 Joe & Pat’s or Pal Joey’s. Iconic dining spots on Victory Blvd, famous for Italian specialties, competing for the best slice in Staten Island, 1960.

#127 The Black Horse Tavern Located at Richmond and Amboy Roads in New Dorp, Owned by the Vanderbilt Family, Circa 1930.

#128 PS 14 Was Located on Broad Street, Stapleton, Torn Down in 1962, Relocated to 100 Tompkins Avenue, 1962.

#129 Workers Grading the Dirt Roadbed at Intersection of Corson Avenue and Victory Boulevard, Circa 1903.

#130 Grocery Customers Patronized the Houseman House at Richmond Terrace and John St., Circa 1895.

#132 Hylan Blvd. Looking North from New Dorp Lane Featuring a Mini Golf Course, a Mobile Gas Station, and a Bar, 1951.

#133 Port Richmond Avenue Looking North; Comparison of 1951 and the Present, 1951.

#134 Victory Boulevard, once called Richmond Turnpike, renamed post-WWI, still rural in the early 20th century.

#135 A boarding house that once stood at the corner of Bloomingdale and Woodrow roads where 137 homes were built.

A Boarding House That Once Stood At The Corner Of Bloomingdale And Woodrow Roads Where 137 Homes Were Built.

The house was lived in by some of the Sandy Ground oystermen who settled in the community in the 1830s and 1840s. Sandy Ground was a community of oystermen who worked the shellfish beds of the Raritan Bay. They had boats and they knew the local waters well.

#136 Vintage postcard of Eltingville train station on Richmond Avenue from 2016.

#137 Masonic Hall and Post Office on 514 Bay Street, Stapleton, 1900

#138 Members of Engine Co. 160, established 1915, with their Nott steam pumper.

#140 Charlie’s Drive-In at 2990 Richmond Ave., New Springville, 1956.

#141 Wagner’s Garage, 658 Richmond Rd., Now All City Collision, 1928.

#143 Schuler’s Delicatessan, 508 Midland Avenue, now the All Night Long Deli, 1925.

#145 The Palace offers dry cleaning for 75¢, celebrating 12th anniversary, 1932.

#146 Store of a Million Items: Located at 108 Canal Street, top photo from the 1950s.

#147 Antonio, Sadie DiBlasi, Joseph, and Nellie Teracina pictured in front of the DiBlasi & Co. Fish Market, Castleton Ave., circa 1917.

#148 This string of brick homes on the south side of Cheshire Place was built in the late 1930s by John West.

#149 Eltingville train station overpass, 1939; enabled unimpeded local traffic.

#150 Arlington Avenue at Richmond Terrace, Looking South; Mariners Harbor Not Much Has Changed, 1961 and 2016.

#151 The W.T. Garner Mansion, one of the few pre-Civil War mansions in New York City, became St. Austin’s School for Boys in the 1880s, and later the original building of St. Vincent’s Hospital, 1903.

#152 A 1939-41 snapshot of stores at 61-63 Victory Boulevard, including Rubsam and Horrmann beer, a bake shop, and more. Second photo is from 2018

#153 Shops on Port Richmond Avenue at Richmond Terrace in the 1920s; some buildings still stand, 2016.

#154 Sunset Bowling Lanes in New Springville was a popular bowling alley that closed in 1994.

#155 Richmond Avenue: A 1909 view looking north to Bulls Head from near Signs Road.

#156 The bus stop on Port Richmond Avenue, near Harrison Avenue, in front of a boarded up candy store in February 1985.

The Bus Stop On Port Richmond Avenue, Near Harrison Avenue, In Front Of A Boarded Up Candy Store In February 1985.

The graffiti is gone but the people still gather at a bus stop on Port Richmond Avenue, near Harrison Avenue, in front of a closed pharmacy. May 9, 2016.

#157 Charlie’s Drive-In Fountain Service in New Springville, 1956; now an open space with a park path, captured in 2016.

#158 2561 Hylan Blvd., New Dorp now hosts the Hylan Diner but was once the home to Bistro, Enza’s, Hedges and Bacci’s Charcoal Haven.

#159 Clove Lake Stables, founded in the mid-1930s, was a popular riding academy that closed in 1985.

#160 Van Duzer and Broad Streets, Stapleton captured in both 1927 and 2014.

#161 Thomas Wiberly’s Broadway Café, Castleton Avenue and Broadway, featured Rubsam & Horrmann beer.

#162 The Oakwood Shopping Center, Amboy Road and Clarke Avenue.

#163 Richmond County Fair in Dongan Hills; from 1905 glory to its 1926 end.

#164 Bistro at 2561 Hylan Blvd., New Dorp; from Bacci’s to Hylan Diner.

#165 Buel Avenue, Dongan Hills, features a railroad crossing built in the early 1900s, post-Civil War.

#166 Swiss Chalet, once located at 18 Nelson Avenue, was a Great Kills staple.

#167 1803 Victory Blvd., Castleton Corners circa early 40s and in 2013.

#168 Stapleton Chop House was located 519-521 Bay Street, The sign reads: Lunch 80¢

#169 Silver Lake Golf Course opened in 1930. Now part of Parks Department Silver Lake Park house.

#170 Millard Fillmore’s in Travis; a cozy, Cheers-like atmosphere, opened 1986, closed 1999.

#171 The HoneyComb, a vendor area in Staten Island Mall, existed from the late ’70s to early ’80s.

#172 The Boulevard: A 1899 view showing University Temple, now part of the Westerleigh community.

#173 Marina Cafe: Opened in 1980 on Staten Island’s southern shore, it was originally built on the remains of the Richmond County Yacht Club and Harbor House. Suffered severe damage in Hurricane Sandy but fully renovated since.

#174 Weissglass Dairy, founded by Julius Weissglass in the late 1880s, was a prominent milk processing plant. Closed in Staten Island in 1975, moved to Queens.

#175 The Alvin Conklin Planing Mill, once situated on Richmond Terrace in Port Richmond, later became Farrell Lumber and is now closed.

#176 Richmond Avenue looking north to Bulls Head from Signs Road, captured around 1909.

#177 Van Duzer and Broad Streets, Stapleton 1927 and 2014.

#178 Hylan Blvd: View from Old Town Rd in both 1939 and 2014.

#179 Beach Park Drug Co., 612 Midland Avenue, Midland Beach.

#180 View of Forest Ave. at Bard Ave. in West Brighton, 1951.

#181 Henny’s Steakhouse in Stapleton, originally Fritz’s in 1890, became Henny’s in 1948. Destroyed in 2002, it reopened after renovations.

#183 Former Masonic Hall on 514 Bay Street in Stapleton, designed by Edward A. Sargent. Once home to the Stapleton Branch Post Office, it now houses Project Hospitality.

#184 Intersection of Morningstar Road and Richmond Avenue, depicted in 1886 and contrasted with its 2011 appearance.

#185 Spanish Camp in Annadale was a unique cooperative community founded by Spanish immigrants in 1923, demolished in the 21st century.

#186 ’90s Video Stores: The golden age of VCRs, featuring Blockbuster, Palmer Video, Hollywood Video, and West Coast Video.

#187 South Beach Amusement Park entertained for decades. Closed by Robert Moses in 1955 for a never-built Shoreline Highway. Second photo is from 2011

#188 Eltingville Store, a wood frame building, now a print shop at Historic Richmond Town.

#189 Victory Diner in Castleton Corners opened in 1932 and closed in 2007; a popular community hub. Second photo is from 2008

Written by Wendy Robert

Brand journalist, Ghostwriter and Proud New Yorker. New York is not a city – it’s a world.

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