Searching through early issues of The Rye Chronicle, The Rye Record’s precursor, I noticed distinctive drawings by an artist named Whitman Bailey.
Delving deeper, I discovered that The Chronicle published nearly 70 memorable scenes of the changing face of Rye, sketched by Bailey in black and white.
Howard Archer, the Chronicle’s longtime editor and publisher, commissioned Bailey to do the first of these drawings for the issue of Jan. 26, 1924. Placed prominently on the front page, it is a view of the Square House from the rectory of the Church of the Resurrection, which was then located near the corner of Purchase Street and the Post Road.
Beneath the drawing, Archer introduced Bailey to readers of the Chronicle:
“This sketch was originally drawn for The Rye Chronicle by the well-known newspaper artist, Whitman Bailey. Mr. Bailey’s work has appeared in a number of the leading newspapers of New England, and of late he has been sketching in this section of the country. Many of his drawings have appeared in the Stamford Advocate, Norwalk Hour, Westport Herald, and New Canaan Advertiser, etc.”

It appears that Archer helped Bailey choose his early scenes of the downtown area, including the library, fire house, and village green. There were many scenes of the Milton area, drawn in the 1930s, when it was still home to ship building.
Rye’s waterfront had great appeal for Bailey, judging from the number of scenes he drew of Manursing Island, Playland, Rye Town Park, and even the rocks off Milton Point, known as the “Scotch caps.”
Over the years, Bailey drew many views of Rye’s churches, schools, and clubs, perhaps because Archer knew they would appeal to a wide cross-section of his newspaper’s readers. One scene, published in 1924, shows the newly opened Westchester Biltmore Country Club (the original name for Westchester Country Club) with a vintage automobile driving along an avenue of recently planted trees.
Most of the drawings published in 1924 appeared on the front page of The Chronicle and were accompanied by Archer’s commentary about the historical or contemporary significance of the scene. In later years, his drawings appeared on inside pages with comments written by Bailey.
The last of his drawings appeared on the front page of the Chronicle in 1942. Captioned “New Public Building for Rye,” it depicted the current home of the Rye Art Center, which the lead article noted, was “used as a place of worship by parishioners of Christ’s Church after the Revolution.”
Born in1884, Bailey lived in Providence, R.I., until he graduated from high school. Although his father, William Whitman Bailey, was a noted professor of botany at Brown University, Whitman developed artistic rather than academic talents at a young age.
There are some descriptions of his youth in “Goodbye, Proud World,” a memoir written by his younger sister, Margaret, including her last mention of his leaving home: “He was at Howard Pyle’s school in Wilmington, learning how to draw. He was going to be an illustrator like the great Howard Pyle himself and do pictures for stories that came out in Century or Scribner’s.”

By the time Bailey became one of Pyle’s students in 1901, at age 17, Pyle was widely admired as an author and illustrator of numerous books. His reputation as an artist and teacher continued to grow, and he is now generally considered the father of American illustration art.
The fame of Pyle and his students grew especially during a period when new technology created great demand for color illustrations by publishers of popular magazines like Harper’s Weekly and Scribner’s.
Yet, shortly after Bailey started his studies, Pyle discovered that Bailey was color blind. Still, Pyle told him: “Whitman, you do not need to give up your artwork, because you are color blind. You have a rare understanding of shades between black and white, and I think you have a future in that field.”
Following two years of study with Pyle, Bailey moved to New York and took courses in fine and applied arts at the Pratt Institute. After his father died in 1914, Bailey returned to his family home in Providence and succeeded in having many of his drawings published in the newspapers of Boston, Providence, and elsewhere in New England.
His success as an illustrator continued when he moved in 1923 to live with his sister in New Canaan, Conn. After submitting some sketches to the editor of the Stamford Advocate, Bailey was commissioned to do one sketch a week of scenes in Stamford and its surroundings. By the time of his death in 1954, more than 600 drawings of Fairfield County scenes had been published in The Advocate and other newspapers.
Bailey apparently enjoyed drawing scenes of Rye enough to continue coming here for almost 20 years, despite the long drives. He must have had a special affinity for the many historic landmarks, its waterfront, and the resemblance of the Milton boatyards to some of the Rhode Island maritime communities of his youth. It is also likely that he and Archer were kindred spirits in their love of local history.
After Bailey died in 1954, many of his drawings were republished periodically in The Chronicle until Archer’s death in 1975. In the issue announcing Archer’s death, published by his son, a full page carried four Bailey scenes.

The heading stated:
“Mr. Bailey was a well-known artist and drew these scenes for The Rye Chronicle over thirty-five years ago. The drawings are part of a collection of scenic spots dear to the memory of many of our residents.”
While photographing drawings found in the Chronicle, I discovered that the archives of the Rye Historical Society held nearly four dozen print blocks with scenes drawn by Bailey. These had been used by The Chronicle and had been donated to the historical society by a member of the Archer family.
After discussions with Anne Gold, until recently the executive director of the historical society, I chose the Center for Contemporary Printmaking in Norwalk, Conn., to make prints of Bailey’s drawings from the blocks. They did excellent work, but there were still 25 drawings for which there were no print blocks.
Fortunately, Jim Frank, a professional photographer and emeritus professor of digital media at Manhattanville University, had just joined the historical society as resident artist. Using his broad knowledge and skills with a digital camera, the remaining images were artistically completed.