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| Date: | 1900 |
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| Description: | A seated portrait of Aaron Middleton, who is holding a book. Middleton was the father of William Middleton and father-in-law of Clara Middleton. |
| Date: | 1910 |
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| Description: | A seated portrait of William Elwell Middleton, wearing a suit. |
| Date: | 1905 |
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| Description: | Forest Middleton sleeps on a settee as his father, William, reads and his mother and Grandmother Joanna Middleton sit nearby. |
| Date: | 1918 |
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| Description: | Forest Middleton, wearing eyeglasses, holds Leonore Judkins Middleton on his lap. She is crocheting as he rests his head on her bosom. |
| Date: | 1890 |
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| Description: | Head and shoulders wedding portrait of William Elwell Middleton and Clara Case Middleton. |
| Date: | 1900 |
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| Description: | Head and shoulders portrait of Forest Middleton wearing matching knit sweater and long stocking cap with tassel. |
| Date: | 1897 |
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| Description: | Forest Middleton rests his arms on a press-back chair. He wears a hat and winter coat. |
| Date: | 1910 |
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| Description: | William Middleton, dressed as a chef, poses holding a bowl on a plate. He is wearing pince-nez glasses. |
| Date: | 1905 |
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| Description: | Oval portrait of Clara Middleton sitting on a settee with a book, wearing a fine skirt and blouse. |
| Date: | 1912 |
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| Description: | Forest Middleton and his future wife, Leonore Judkins, look over a piece of beadwork on a frame. |
| Date: | 1910 |
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| Description: | Forest Middleton, wearing eyeglasses and holding a musical score, sits with his back to an upright piano. |
| Date: | 1905 |
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| Description: | Mrs. Aaron (Joanna) Middleton sits at a table with her hand resting on a book. She was the mother of William Middleton, and mother-in-law of Clara Middleto... |
| Date: | 1910 |
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| Description: | Photographic postcard of Forest Middleton, with a pensive expression with hand on his chin, sits with his dog in his lap. |
| Date: | 1900 |
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| Description: | Clara Middleton poses seated in a chair, reading. She is wearing a narrow fur stole over her shoulder. |
| Date: | 1905 |
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| Description: | A rabbit, one of many pets belonging to the Middleton family, sitting on an upholstered stool. |
| Date: | 1910 |
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| Description: | The Middleton family cat poses near a basket on a table which is covered by an oriental carpet. |
| Date: | 1905 |
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| Description: | Clara Middleton, well-dressed and wearing a large hat, holding her pet fox terrier's chin as the two share a gaze. |
| Date: | 1909 |
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| Description: | Two hares rest on rugs in the Middleton family apartment. Two plants in large jardinieres are also featured. |
| Date: | 1908 |
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| Description: | Clara Middleton lies on a love seat with her feet supported on a folding rocking chair. |
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