Walking Tour of the Historic District of Greenport Village, NY

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Tour Route Options: A walk tour map legend A B walk tour map legend B walk tour map legend B alternate

walking tour map Go to Ireland House Go to Tour Stop #1 Go to Tour Stop #2 Go to Tour Stop #3 Go to Tour Stop #4 Go to Tour Stop #5 Go to Tour Stop #6 Go to Tour Stop #8 Go to Tour Stop #9 Go to Tour Stop #10 Go to Tour Stop #11 Go to Tour Stop #12 Go to Tour Stop #13 Go to Tour Stop #14 Go to Tour Stop #15 Go to Tour Stop #16 Go to Tour Stop #17 Go to Tour Stop #18 Go to Tour Stop #19 Go to Tour Stop #20 Go to Tour Stop #21 Go to Tour Stop #22 Go to Tour Stop #23 Go to Tour Stop #24 Go to Tour Stop #25 Go to Tour Stop #26 Go to Tour Stop #27 Go to Tour Stop #28 Go to Tour Stop #29 Go to Tour Stop #30 Go to Tour Stop #31 Go to Tour Stop #32 Go to Tour Stop #33 Go to Tour Stop #34 Go to Tour Stop #35 Go to Tour Stop #36 Go to Tour Stop #37 Go to Tour Stop #38 Go to Tour Stop #39 Go to Tour Stop #40 Go to Tour Stop #41 Go to Tour Stop #42 Go to Tour Stop #43 Go to Tour Stop #44 Go to Tour Stop #45 Go to Tour Stop #46 Go to Tour Stop #47

Begin the tour at the Stirling Historical Society, housed in the Ireland House and the Berger House (a small building to the left).


Ireland House, 319 Main Street  c. 1750s
On the north side of the village parking lot and north of the gazebo. Ireland House is the home of the Stirling Historical Society. The house was built in the early 1830s on the south side of Adams Street about 100 feet from its present location. The house was home to numerous Greenport working families many of whom rented from the property owners.

The house style is Greenport Vernacular, a common house form built from the 1750s. It is a simple small-scale half house with a plain façade, painted clapboard, a doorway with sidelight and transom and 6/6 pane windows. It is a half house because windows are on one side of the front door.

In 1973, Mr. and Mrs. Frederick Preston donated the house to the Stirling Historical Society and in 1976, the Society moved it to the present location at 319 Main Street.

The Society named the house after Margaret E. Ireland, a well known civic worker and an admired, colorful resident of Greenport. She was a newspaper correspondent for the NY Herald Tribune, the NY Journal American and local papers; a tireless fund raiser for Eastern Long Island Hospital and Burton Potter Post American Legion, and matron of Greenport Police Department. Ms. Ireland's grandparents lived in the house in the late 1800s and raised their family there. Later Ms. Ireland's parents, James and Margaret Grady, lived in the house and when Ms. Ireland returned to Greenport in 1918, she also took up residency with her children. She lived in the house until her death in 1962 at the age of about-83. Because Ms. Ireland said, "ladies never tell their age," the family cannot confirm her date of birth. Photo


You have two walking options. Face east towards Bank of New York across the street and either A, walk down Main Street south toward the waterfront, circle around by way of Carpenter, Bay, Central and back onto Main, or B, walk north on Main to Memorial Park, left to First Street and then south on First back to the village. See map on back cover for routes.

Tour A

#1.  Bank of New York Building, 238 Main Street  c. 1864
Built by Charles Langton Corwin for the First National Bank after the bank received the first national bank charter on Long Island in March 1864. The bank is one of the last original brick structures and the only original of its period in this sector of Main Street. The second story, side and rear sections were added between 1897 and 1909. The brackets are cast iron; sills and keystones are granite. The first drive-up teller window on Eastern Long Island was added in 1958. Photo

#2.  Reeve Building, 210-212 Main Street  c. 1873-90
This is one of the most ornamental commercial structures in the business district. It has an arched parapet with wide bracketing and dentil work along the cornice with wood lettering that spells Reeve's Building. Note the scalloped shingles and ornate false front at the roofline. The Freemasons met on the second floor for years before completing the Johnston Memorial Masonic Temple located at 430 Main Street in 1901. Photo


#3.  Kramer Building, 206-208 Main Street  c. 1850's
A fine Italianate brick store and key building in the heart of the commercial district, this is one of the few buildings of this type and vintage that were not lost to fire or random replacement. The first of three druggists to occupy the building was G. H. Corwin. A rear addition housed the first telephone exchange in Greenport in 1906 and in the 1920s, a speakeasy was situated on the second-floor rear. Photo

#4.  Whitney Hubbard Gallery, 207-209 Main Street  c. 1858-73
Over the years and even today, this building was most often used as a studio or art gallery. It was the gallery of famous American Impressionist artist Whitney Hubbard (1875-1965) whose works are shown in the Corcoran Gallery, Brooklyn Museum, Connecticut Academy of Fine Arts, the Atlanta Museum and numerous others. Photographers rented studio space from 1897 through the 1920's. Frank Hartley and Hugo Frey were among the other notable tenants. Photo

#5.  Claudio's, 111 Main Street  c. 1838-58
Manuel Claudio arrived in Greenport aboard the Portuguese whaler Neve in 1854. Upon retirement in 1870, he established a saloon on lower Main Street. He later acquired the present property at the Main Street Wharf and opened the restaurant and a hotel. Claudio's quickly became an integral part of the Greenport harborscape and has been operated by the Claudio family ever since. The building, on the National Historic Register since 1945, has a two-story enclosed porch and paneled door entries with spindled brackets. Inside is an ornate mirrored bar that Manuel salvaged from a New York Bowery hotel and installed in 1886. Photo


#6.  Preston's, 102 Main Street  c. 1873-82
This site is symbolic of Greenport: Since 1827 when Main Street was laid out with the wharf at its foot, ship captains met, provisioned and transported people and products from this location. The main building complex facing Main Street consists of two joined stores and a separate shop that was formerly a coal storage building. The latter was moved by the Navy in WW II and used as a machine shop for boat repairs and construction. Over the years, Preston's has serviced and provisioned a large assortment of yachts, including those of the Vanderbilts and the Astors. Photo

Walk North on Main and turn right on East Front Street to Carpenter Street.

#8.  Greenport Yacht & Shipbuilding, 201 Carpenter Street  c. 1860
The configuration of the marine railway in this yacht yard has remained relatively unchanged since its installation in the 1850s. Boats of up to 1000 tons can be hauled on it. In the early 1900s, members of the New York Yacht Club had their boats overhauled here and America Cup contenders recruited crew from the yard. During World War II, the yard employed 1200 employees who worked on the construction of minesweepers and landing craft. Photo


#9.  Jail House, 232 Carpenter Street  c. 1910
This was the village's first official jail; its predecessor was a tool shed behind the old village hall. The village lock-up was called The Greenlight Hotel because when occupied, a green light in front was turned on. Located in the historic commercial district, the jail stands out because of the barred window and all-brick exterior. The jail has three cells with pressed tin walls. It is no longer used in its official capacity. Photo

Turn East (right) on Bay Avenue.

#10.  151 Bay Avenue  c. 1837/1897
This location is an important introduction to the residential neighborhood that borders the village's commercial center. The house originally on the site was moved and only the rear kitchen wing was kept when the main Queen Anne house was built prior to 1897. John G. Champlin, grocer and dry goods, was an early owner of the 2 1/2-story house. There is a wrap-around porch and 5-window bay on the first story with tower above. Double-bracketed cornices are featured throughout. Photo

#11.  168 Bay Avenue  c. 1859/1863
One of several large Bay Avenue homes built by the rising merchant class of Greenport. Italianate style with double bracketed cornice above two open front porches with tapered square columns. Porch columns have beveled corners that create illusion of arches; the single porch rail has decorative bracketing along the bottom. Eastern front door is flanked by sidelights with etched floral pattern. Photo

#12.  Kendrick House, 152 Bay Avenue  c. 1810
D. Kendrick, a ship carpenter, was the original owner of the house that is the oldest on this tour. This small Greek Revival gem is one of the few 1 1/2-story houses on a 2-story block. Photo

#13.  Lyons House, 141 Bay Avenue  c. 1873-90
The house was originally owned by the Lyons, a prominent family in 19th century Greenport that included a lawyer and department store owner. The building is a 2-story Italianate with flat roof, double bracketed cornice and ornate widow's walk with arched windows on 4 sides. The porches have gingerbread railings, decorative brackets and square columns. Photo

#14.  122 Bay Avenue  c. 1858-73
One of the more original houses on the block. The front door is located directly below a center gable and has a gabled pediment with square columns. Long 2/2 windows flank the front door and are in the gable above the door. The house has irregular bracketing and 3/3 eyebrow windows on the front 2nd story. B Before heading one block north (left) to Central Avenue (Tuthill Street prior to 1897), take a moment to admire the bay view from the public dock at the end of Bay Avenue. Photo


#15.  123 Central Avenue  c. 1838-58
One of the major houses on the street and originally part of the Tuthill estate. Remodeled in the mid-1890s. This is a flat-roofed 2 1/2-story house with a front porch that wraps to the east side. The porch has square column bases, paired brackets, decorative finials and spindle balustrade. The front door is Greek Revival. The first floor windows fronting the porch are 9/9 floor-to-ceiling. Photo

#16.  145 Central Avenue  c. 1838-58
One of the few examples in Greenport of a 1 1/2-story half-house that developed into a full house. The first portion was built between 1838 and 1858; the west half was added between 1858 and 1873 when the A. Waynes family were residents. Photo

#17.  163 Central Avenue  c. 1875
The house belonged to George Webb, a ship painter and dealer in paints and oils. It is a 2 1/2-story building with a 1 1/2-story eastern wing. A one story porch with turned columns on pedestals extends across the frontage of both wings. This is an excellent example of Italianate architecture that retains many notable features of the style. It has excellent bracketing and an articulated entablature over the main doorway and sidelights. Photo

#18.  320 Carpenter Street  c. 1815
On the southeast corner of Central and Carpenter is a smaller scaled, 1-story 3-bayed house built in Federal style near the beginning of the 1800s. This is one of Greenport's earliest surviving residences. Pilasters and a decorative pediment with dentiled cornices flank the centered front entry. The house has three small eyebrow windows of 12 panes each located under the eaves. Photo

#19.  510 Carpenter Street  c. 1840s
The original 2-story house, built in the 1840s, is small and narrow and can be seen at the rear of the property. It was moved to give frontage room to the new cross-gabled house built in 1873. The houses are good examples of the simple Victorian vernacular for working class families of the time. Photo

#20.  515 Carpenter Street  c. 1909
This former boathouse was moved from the Mitchell property at the foot of Bay Avenue in 1971 and extensively renovated in the late 1990s. It is a 2-story house with a deep sloping gambrel roof. Large double doors with diamond windows face north and south. It is on a small lot and is one of the few residences on the west side of Carpenter since Main Street properties extended through to Carpenter. Photo

#21.  608 Carpenter Street  c. Late 1800s
Sitting close to the street, this is one of several original saltbox homes on Carpenter Street. These small old houses are sited close to the street on deep narrow lots. They compliment and add to the diversity of architectural styles on the street. Photo

Return to Main Street on Case Street and as you head south back toward Ireland House, you will see Tour B properties #22 through #31 in reverse order.

Tour B

#22.  Stirling Square, 302-310 Main Street  c. 1880s
The corner complex includes 1885 Arnott's drug store (see stained glass on south side), Swain's Livery with carriage house and auto barn at east rear and a gabled house on the north frontage unchanged by commercial use. The drug store has heavily sculpted bracketing along the Italianate roofline. Photos

#23.  Walter Havens Cottage, 425 Main Street  c. Early 1800s
In 1864-65, this was a country store owned by Walter Havens. It is a fine example of a Cape Cod half-house. The doorway is Greek Revival with slender round pilasters. The eight-paneled door has bentwood sidelights with a matching transom above. Photo


#24.  The Times Building, 429 Main Street  c. 1909
The name appears on the building frontage above the Ionic relief columns that separate the multi-paned display window. This was the first permanent office of The Suffolk Times, a weekly newspaper published in Greenport from 1857 until 1989. The weekly continues to document Greenport and Long Island's East End from its present office in Mattituck. Photo


#25.  Phillips House, 433 Main Street  c. 1830; rebuilt 1860
Named after S. W. Phillips, president of the Peoples National Bank in the late 1880's, the house is one of the most decorative buildings in this sector. It has a scalloped slate roof, massive decorative woodwork, heavily bracketed mansard roof, and a carriageway through south wing. A notable feature is the pair of white cast iron lions straddling the front steps. Photo

#26.  Timson Hotel, 437-455 Main Street  c. 1830
The 3 1/2-story north section was the original construction with the 2-story south wing added after 1890. The hotel was located at an important juncture of Main and Central Avenue. When the wharf at the foot of Central Avenue was completed in 1838, the hotel was in an excellent location to receive guests from the boats that docked at the wharf. It was also two blocks from Stirling Hall (located at the southeast corner of Main and Bay) that provided entertainment to guests and Greenporters until it burned in 1899. Photo


#27.  Greenport Auditorium, 434 Main Street  c. 1894
The Auditorium is a large, handsome and impressive Queen Anne structure built through the "pluck and public spirit" of Miss Sara Adams to "uplift the moral tone of the community." The architect was George H. Flack and the builder was Charles Corwin. Until 1938, the Auditorium was the center for cultural entertainment that included serious drama, vaudeville and band music. Despite its current use as a furniture store, the owners have preserved the interior – its dressing rooms in the basement below stage, the curved balcony with ornate metal grillwork and the stage are in excellent condition. Photo

#28.  H. E. Wells House, 455 Main Street  c. 1873
This large Queen Anne house was built in front of a house built in the early 19th century. The street frontage shows two bay windows and heavy paneled doors with cast hardware. The façade has scalloped shingles, large clapboards and a sunburst design at the peak of the roof. Mr. Wells, the original owner, discovered the bunker process of extracting fish oil. Photo

#29.  500 Main Street  c. 1858
The house marks a border between the commercial developments on lower Main Street near the wharfs and the residences built primarily for merchants to the north. Built in Greek Revival style, a distinguishing feature of the property is the two-story porch that was added between 1890 and 1897. The porch has four 8-sided columns topped by double brackets and 4/4 porch windows that extend to the porch floor. Photo


#30.  Captain Wells House, 530 Main Street  c. 1864/70
Italianate villa of grand proportions built for Captain Wells at the height of the whaling industry. The house has twin-arched windows on all sides of the tower and elegant arches on front porch. After losing his whaling fortune, Captain Wells had his ship, the Swallow, enlarged and went to Africa to obtain slaves. He collected the human cargo and started homeward but was never heard of again. The crew, however, arrived safely, sold the slaves and the ship. Photo

#31.  Captain Case House, 527 Main Street  c. 1850/70
Ebenezer W. Case lived here through the above period. The 2 1/2-story house with mansard roof, embellished in 1870, is vintage Victorian. It is bracketed French Second Empire style with side bay window, jigsaw porch detail, dentils under window caps and a double front door. Photo

#32.  Grosvenor C. Adams House, 630 Main Street  c. 1870
Mr. Adams was the president of the First National Bank from 1864 when the bank was chartered until his death in 1883. The house is Queen Anne style with inverted truncated shingles on gable pediments. Bracketed cornice, double front door with round head; 2-story south bay with paneled dado. Notable entablatures on rear porch door and windows. Photo

#33.  Conklin House, 636 Main Street  c. 1820
This Greek Revival house was built for the Conklins by Orin Wiggins and is one of the older structures in this area of Main Street. It is a 1 1/2-story cottage with a hand-constructed window and door cornices. Much of the original detail is intact. Photo

#34.  Civil War Monument, Broad and Main Streets  1883
"The community is indebted to the energetic work of the ladies of the Soldiers Aid Society" for the Soldiers Monument and were assisted by comrades of the Edward Huntting Post II G.A.R. Beginning with a Fourth of July benefit dinner, the ladies of the Soldiers Aid Society raised the funds ($1,000) for the monument. The Quincy granite monument is a tribute to the death of 29 Greenporters. It was installed in November 1883 and dedicated on Decoration Day 1884. Photo

In early years, the convergence of Main, Broad and Stirling Streets was called Steamboat Corner and led to the docks in Stirling Harbor. People gathered here to watch the boats in the harbor and share tales of sea adventures.

You have the option of walking along Stirling Street to house #35 and then on to views of the marinas of Stirling Harbor where Greenport was first settled. Stirling Street/Avenue links back to Carpenter Street at #20 on Tour A. (see second option below)

#35.  162 Stirling Street  c. 1883
This prominent waterfront site was the location of the T. Hempstead pottery prior to the construction of the house by Mr. Beck, president of N.Y.C. Fire Insurance Co. The house, set on spacious grounds, has several unique features some of which were added in 1908: Palladian style window in the front gable; wood fanlight carving in gable tip; scalloped shingles with finial-like ornaments; double front doors with large beveled glass windows and a turret. Photo

OR... continue on Tour B north along Main Street to Memorial Park and then south on First Street where you find many fine examples of late 19th century residences.

#36.  Townsend Manor Inn  c. 1835, 1858
(a) 714 Main Street 1835
One of three buildings comprising the inn property. The highly visible house, residence of whaling Captain George Coggswell, has a two-storied columned façade with dominant exterior moldings. The property backs onto Stirling Creek thereby providing boat dockage. Captain Coggswell moved to California in 1849 though Widow Coggswell was in residence in 1858.

(b) 726 Main Street c. pre 1858
Architecturally, the Gingerbread House represents a highly individualistic handling of Italian elements by an unknown architect. Its elaborate cornice has large and small fleur-de-lis motifs. The front door transom and sidelights have very rare, original, stained dark red and blue windows with cutout, stencil type designs. In 1858, the house was the residence of G. Cripps. Photos

#37.  Memorial Park, Main and First Streets  
The small triangular park is located where First and Main Streets converge. The park has three monuments dedicated to the memory of Greenporters who served in the U.S. military in World War I, World War II or the Vietnam Conflict. Photo


#38.  633 First Street  c. 1870
The house was the 1873 residence of G. H. Cleaves, a druggist who worked for G. H. Corwin. It is a large two-story Italianate with flat roof. The exterior and interior are rich in late 19th Century detail. Exterior has paneled fascia board with double solid ribbon brackets. A side porch was added in 1897 and extended prior to 1909. Photo

#39.  602 First Street  c. 1850
This fine example of Italianate style was built in 1850. The second-story arched window carry upward the effect achieved by the arched front door with its etched ruby glass sidelights. Brackets and all exterior woodwork are well proportioned and executed. Note the finely detailed half octagonal bay window on the south elevation. Between 1897 and 1909, the cupola was removed and the roof changed from slate to shingle. Photo

#40.  603 First Street  c. 1847
In the 1850s, Captain Tyler owned the house. One of the few brick buildings in the village, this residence is an excellent example of Federal style with elegant Greek Revival elements. The columned portico doorways are outlined by narrow sidelights and transom and dentils under the eaves. Note the balance achieved by the matching entries facing the two corner streets. Photo


#41.  Floyd Memorial Library, 110 North Street  1917
The funds ($30,000) to construct the library were donated by Miss Grace Floyd in memory of her father, David Gelston Floyd, a whaler, banker and grandson of General William Floyd signer of the Declaration of Independence. The library was designed to resemble the Floyd homestead, Brecknock Hall on Sound Avenue, and the stones came from the estate's quarry. D. Stanley Corwin completed the construction in 13 months. In 1998, the 3-story west wing more than doubled the size of the library. Photo

#42.  529 First Street  c. 1874
An inscription on the basement wall dates the house June 1874 for the owners named Hubbard. An extremely fine building set farther back from First Street like its neighbors at 519 and 525. It has a distinctive Mansard style with Italianate details that include fine bracketing, window caps over second-story dormers and scrollwork under eaves. Photo

#43.  Andrew Wiggins House, 519 First Street  c. 1858
This house, a conglomeration of Italianate and Mansard styles, contains some of the finest exterior trim and features found in the area. The exceptional workmanship is by Andrew Wiggins, carpenter, who built the house for his own family. Elaborate bracketing, dentil work, arched window caps and paneling are visible on the front of the house. Look toward the back of the left side of the house to see a continuation of the beautiful woodwork on the side porch. Photo


#44.  Whitney Hubbard House, 511 First Street  c. 1858/73
Late Greek Revival doorway with interesting turned trim on door pilaster. Note dentils under roof eaves and door cap, and double arched windows in gable. Whitney Hubbard, notable Long Island Impressionist painter, inherited the house from his father, Elijah, a confectioner. The family retained ownership from 1880 to 1965. Whitney's studio was on Main Street. Photo


#45.  Ackley House, 509 First Street  c. 1845
Ackley House is one of two brick residences (the other is #40) in Greenport. Its style is Federal while the entry door trim and sidelights are Greek Revival. Note the elegance achieved by the row of windows on the second story and the attractive dentils at roofline and around door portico. There has been very little change in the exterior and interior. Photo

#46.  William Corey House, 440 First Street  c. 1882
Small village estate built by William D. Corey of Webb and Corey, a major port chandlery. The house's roof is slate with a Victorian cast iron roof railing outside the third story. The façade has scalloped shingles and decorative brackets. An Ionic-columned porch wraps the front and south side of the house providing access to the Colonial doorway with arched transom and sidelights. When built, it was reported to be "one of the handsomest places in Greenport – everything about it is as neat as a pin." Photo

#47.  Hartley House, 437 First Street  c. 1882
This is a late 19th century, 2 1/2-story cross-gabled house with fine decorative woodwork on the porch and in gables. Most windows have pediment molding; small cathedral windows in each of the four gables. The house was the residence of Charles W. Hartley, a harness maker who in the 1880s located his business near 1st and Front Streets. Photo

Tour B ends here. Return to Ireland House by walking east through the village parking area.

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