The ‘Art’ of Storytelling on a Walking Boston Private Tour

New artwork transports you back in time and enhances your tour experience

Private tour guide Ben Edwards, who already shares maps, photos, rare documents and historic newspapers on his route, was looking for an additional way to support his storytelling and bring historic Boston to life. The skills of artist Cortney Skinner instantly came to mind. Their recent collaborations include new illustrations for the second edition of Ben’s children’s book One April in Boston and the Midnight Ride Artwork Project.

To mark the 20th anniversary of One April in Boston in 2020, Walking Boston and Spyglass Books, LLC have commissioned Cortney Skinner to produce a series of original, historically accurate paintings that bring the Colonial Boston Ben’s ancestors knew to life. During the tour, participants will be able to view much of the art while standing in the corresponding present-day locations, and after the tour they’ll receive access to all of the paintings and supporting research online. The first painting in the series “Back Street, Boston April 1775” appears below where it is discussed in detail.

Ben and Cortney have also authored the Spyglass Blog to share the stories behind many of the illustrations he produced for One April in Boston.

painting of the view from Edwards family property in Boston
A view from the Edwards family property in the North End of Boston

For the painting of Back Street (now Salem Street) in the North End in April 1775, Cortney wanted to show a typical day in Boston. He began with a present-day photograph Ben took near the site where the home of his ancestor Alexander Edwards once stood. The painting was to duplicate the eye level, the perspective, and the viewpoint of that photo, transporting the viewer back to April 1775. The route and width of Back Street/Salem Street has changed very little in more than two centuries.

An invaluable resource for the project was “Clough’s Atlas – Property Owners of the Town of Boston based on the Direct Tax Census of 1798” in the collection of the Massachusetts Historical Society. This served as the earliest known accurate evidence of the buildings on Back Street. Though the buildings may well have changed in the 23 intervening years from 1775 to 1798, this atlas provided a good basis for the types of buildings that may have been there in 1775, as well as the property lines of the Back Street neighborhood that Cortney would be portraying in his painting. This section of Back Street is now the part of Salem Street between Bartlett Place and just beyond the intersection of Salem and Prince streets. From the atlas, Ben learned that the Edwards house was a wood-frame structure and not built of brick as he had originally thought. View the location of the Edwards house on this map of the North End in 1775 modified by Cortney Skinner.

None of the buildings represented in the painting still exist with the exception of the Old North Church, whose spire extended above the buildings of 1775 but today is hidden behind the much taller buildings of the present day.

Cortney overlaid an image of the Clough’s Atlas section of Back Street on top of a Google Satellite View of the same area and discovered that not only was Clough’s Atlas remarkably accurate but also that the property lines, alleys and streets of 1798 barely changed in 220 years. Many of the present-day buildings conformed to the 200-year-old property lines. Using Google Earth 3D view, Cortney “flew” around the Back Street neighborhood so that he could visually match the 1798 buildings and property lines with the current buildings. It was through this method that he was able to place the 1775 buildings at the right spot relative to the modern snapshot that Ben took.

Using a printout of Clough’s Atlas, a simple scale model of Back Street was created, using styrofoam shapes for the buildings and an image of Old North Church printed to the same scale as the map. This helped Cortney visualize how the buildings might have looked in perspective when viewed from the point where Ben’s original reference photo was taken. The model also revealed above which buildings the Old North Church steeple would be visible.

The next step was to overlay a perspective grid of Salem Street/Back Street onto the present-day photograph to aid in the creation of the 18th century buildings that would take the place of the modern ones.

Once the basic framework for the painting had been established, the research for the elements of the scene was next. The research may have taken almost as much time as the artwork.

First, the architecture: Using Clough’s Atlas, Cortney matched the possible size and construction of the buildings in that atlas with the ones he’d be painting in the scene. The vernacular architecture of the period as well as that of the North End of Boston was examined, and several examples of those North End buildings (which survived only in antique photographs) were used as guides for the wood-frame, brick-end, or all-brick construction of the buildings on the street. A gambrel-roofed wooden style of architecture was chosen for the ochre-painted Edwards house. Cortney found it interesting that some buildings faced parallel to the street and others were turned at an angle and/or recessed back from the street, making them invisible from the point of view of the painting.

The decision for the colors of the buildings was both an artistic one as well as one of authenticity. Ochre was chosen for the Edwards house so that it would stand out from the rest, which were a variety of natural weathered wood, faded and yellowed white, natural brick, or iron oxide, a ruddy color. The proper period shutters were placed on some of the windows, both for privacy from the busy street traffic and for protection from the elements.

How the paving on Back Street in 1775 would appear was an educated guess since eyewitness or reliable and detailed contemporary descriptions were not found. A mix of cobblestones, oyster shells, stones and pebbles were chosen for the surface, since Back Street was a fairly direct and busy thoroughfare to the waterfront. Tradesmen, deliveries of goods, freight wagons, carriages, horses, oxen, and foot traffic would have required a fairly sturdy surface on which to travel.

Once the buildings, street, and incidental fences, gates, and property line enclosures were established, the scene needed to be populated. Cortney chose a balmy spring day during the first two weeks of April, before the fateful day of April 18, the date of Revere’s ride. Hardy Bostonians would be outdoors carrying on their normal business, a few windows would be open to the fresh breezes, and to all appearances, it might be a normal time in Boston, though an undercurrent of unease would be expressed in hushed comments and whispers exchanged by the populace.

Though Back Street was a very active roadway, Cortney didn’t want to visually crowd the scene with a horde of citizens, however. He wanted to portray a variety of people from a range of social strata and suggest the activity of the times. The clothing worn and vocations portrayed were carefully researched and are typical for the time and place. Learn more about the 19 individuals in the painting and what they are doing on a warm spring afternoon in early April 1775.

About the Artist

Cortney Skinner’s artwork appears in books, magazines, comics and in films. He has illustrated a wide range of subjects including science fiction, classics, horror, fantasy, history, aviation, and children’s books. His landscapes, still lifes and portraits are found in private collections.

Skinner studied illustration at the Art Institute of Boston under Norman Baer, a second-generation student of Howard Pyle, (1853-1911) the famous Golden Age illustrator known for his historic illustrations of the colonial period. Beginning his career in the traditional art techniques of pencil, pen and paint, Skinner entered the digital art world at the turn of the last century.

Cortney’s fascination with the colonial period began when, in the third grade, his class was given a tour of the Revolutionary War period historic sites of his hometown of Cambridge Massachusetts. During the bicentennial, he started the first living history Continental Line Regiment, the 1st Massachusetts Regiment, Continental Line, requiring a great deal of research in order to construct the clothing and uniform of a soldier of the Revolution.

Nestled comfortably in the Shenandoah Valley by the Blue Ridge Mountains of Virginia, Cortney shares a creative life and abode with his wife, writer Elizabeth Massie. To learn more about Cortney, visit

School groups, homeschoolers, and families taking Ben’s tour can access the original art and supporting research online

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