Too often, local history is told from the viewpoint of the men who dominated local government and business. For all of its early history, after all, men were the only ones who could vote or hold local public office.
But even during pioneer times, while it wasn’t easy, women owned Kendall County businesses, farmed, and were property owners.
Life for women without husbands was not easy during the 19th Century, nor for most of the 20th century, for that matter. But some women, through shear ability, intelligence, and fortitude managed not only to survive but to thrive.
One of those successful women was Margaret “Maggie” Shepard Edwards, an Oswego property owner and successful entrepreneur. By the time she died in February 1929, Maggie Edwards was a respected and beloved member of the community.
Margaret Ruth Shepard was born March 8, 1846 in Kendall Township, Kendall County, Illinois, the daughter of a prosperous farmer and his wife, David and Susanna Mary (LeStourgeon) Shepard. Mary died in 1856, and in February 1857, David remarried Elizabeth H. Ewing.
Margaret, called Maggie by her family and friends, taught in one-room schools in NaAuSay Township here in Kendall County before moving on to Centralia to teach school, probably to make more money than local one-room school districts were willing to pay.

She arrived back in Kendall County in July 1874, apparently determined to go into business for herself.
After moving into Oswego from the family farm in 1875, then 29 years old, she went into millinery, the manufacture and sale of ladies’ hats and fashion accessories. A year later, she opened her own milliner shop in the old Smith Building at the northwest corner of Main and Washington. In the summer of 1878, she moved the business to the second floor of the Shaver Building on the east side of Main Street between Washington and Jackson. Five years after that, she moved the business yet again into a former private residence in downtown Oswego.
By that time she was a financial success, and she bought the home in which her business was located a few months later. Only a month after that, she moved the business again, this time to a home on Washington Street.
Maggie Shepard wasn’t just an active businesswoman, she was also active in local politics, even though women didn’t have the right to vote. An enthusiastic Republican, she was a strong supporter of Gen. James A. Garfield during his run for the presidency in 1880. Noted the Kendall County Record’s Oswego correspondent on Oct. 28, 1880: “The Republican meeting Tuesday evening partook of the usual form, the street parade and music preceding the speaking; the youth’s Garfield guards (same might be called the Maggie Shepard company, as she is the funder of it) elicited much attention while on duty in forming the rear of the parade.”
During that era, political parties erected tall wooden victory poles from which they flew political flags and other decorations advertising their candidates. For the 1880 election, the Republicans raised their Garfield pole while local democrats raised their pole to honor their candidate, Winfield Scott Hancock. Wags would sometimes poke their political rivals by sabotaging each other’s victory poles. It appears Maggie Shepard was audacious enough to give Oswego’s Democrats a tweak after Garfield narrowly beat Hancock by less than 2,000 votes.
The week after the election, on Nov. 11, 1880, the Record’s Oswego correspondent reported that: “During one night of last week a black streamer was raised on the Hancock pole, and of course the presumption is that it was done by some one or more of the opposite party, and there are some that think it was Miss Maggie Shepard that did it, which, however, is not very likely to be the case. Maggie was extra zealous in the campaign, and she may have exhibited undue partisan spirit, but I don’t believe she hoisted that flag; no, I won’t believe it.”
In 1885 at the age of 39, probably fearing she would never find a husband, Maggie adopted a five year-old girl, Stella, from the Chicago Orphan Asylum. It is unclear how common it was for single women to adopt children in the 1880s—I suspect it was pretty uncommon—but it’s probably fair to suggest it was also uncommon for a single woman of that era to own her own business and house, not to mention adopt a child.
Then in March 1888, Maggie moved her millinery business one last time, renting the home formerly occupied, and owned, by Oswego pioneer Marcius C. Richards. As a business location, it was a good one, right on one of Oswego’s main thoroughfares.

The house was—and still is—situated on Washington Street across from the Church of the Good Shepherd, adjoining the alley paralleling Main Street from Washington to Jackson Street behind the Main Street brick block. On Jan. 23, 1889, the Record’s Oswego correspondent reported that: “Maggie R. Shepard, Oswego’s successful and popular milliner, has bought the M.C. Richards’ place, of which she was the tenant, and by the way that sagacious new clever correspondent for the Herald has thrown out the hint that Maggie may take in a partner; she is now well fixed for such a step.”
Maggie based her success on hard work and on making sure she always had the latest in women’s fashions available for her customers. Reported the Record from Oswego on Sept. 18, 1889: “Maggie Shepard went Monday to Chicago and will spend several days there selecting goods for the fall stock.”
Proving that love doesn’t come only to the young, Maggie, then 44, married Thomas C. Edwards, a native of Wales and an Oswego hardware merchant, in July 1890. The couple lived in Maggie’s house and milliner shop on Washington Street where she continued to carry on her business. Shortly after the marriage, they remodeled and enlarged the home, including adding a new, fashionable, bay window.
In the fall of 1897, Maggie decided to retire. As the Record’s Oswego correspondent put it: “Mrs. Maggie Edwards, after carrying on most successfully the millinery business here for 20 years, proposes now to sell out and retire. It is the only establishment of the kind in town and hence a good opening for some one to get into a profitable business.”
Maggie’s adopted daughter, meanwhile, grew up in Oswego and kept the name Shepard until her marriage. As the Record reported on June 26, 1901: “One of the prettiest weddings of the season occurred Wednesday evening June 19 at the home of Mr. and Mrs. Thomas Edwards when their daughter, Miss Stella Shepard, became the wife of Mr. Albert L. Woolley, oldest son of Mr. and Mrs. George Woolley. A beautiful new house is being erected about a mile east of town where Mr. and Mrs. Woolley will be at home to their friends after Aug. 1.”
Tom Edwards died Dec. 23, 1911. On Jan. 3, 1912, the Record’s “Tamarack and Wheatland” correspondent remembered Edwards: “A number from here attended the funeral of Thomas Edwards in Oswego. Deceased formerly owned property about a mile and a half west of Tamarack and at one time lived here and had many friends who were shocked to hear of his death.”
With Tom’s death, Maggie continued to live in Oswego where she traveled and enjoyed her daughter and her Woolley grandchildren. She died at 82 years of age on Feb. 17, 1929 in Oswego.
As the Record’s Oswego correspondent reported: “Mrs. Edwards will be remembered as a woman of an especially bright and sunny disposition, which she maintained to the last. She had been failing in health and strength for the last few years and this winter made her home with her daughter, Stella. Gradually, she grew weaker and while not confined to her bed, fell asleep Saturday night to awaken on the other shore.”
Maggie was buried in the Oswego Township Cemetery, bringing to a close a successful, eventful, and well-lived life.
It wasn’t easy for single women to be successful business owners in the 19th and early 20th centuries, but it was possible given sufficient drive and talent. Which, come to think of it, still pretty much holds true today.