Once a vast expanse of open prairie, the area around Greenfield was first settled in 1854.

The state of Iowa was opened to settlers in 1832, but by mid-century, the plains of this area were still foreign to all but a few nomadic Native Americans. Here, the Indians hunted and lived among elk, red deer, buffalo, beaver, mink and an occasional black bear.

Thomas Hodgeson and a man named Hillin were the first to construct pole cabins on the site that would become Greenfield. Neither man owned the land where they settled. That was sold to David Lamb on May 25, 1855 by the State of Iowa. The land was purchased by Milton C. Munger in 1856, who engaged the services of county surveyor D.M. Valentine to plat a town and Greenfield was born.

It is Munger who is responsible for the unique Lancaster style town square in the center of town. The square, with its alleys extending from the corners and streets intersecting in mid-block is one of only a few known to exist. Also included in the original plat of the town was the city park located at Grant and NE Second Streets.

The name Greenfield came from the obvious source: the lush green fields that dominated the plain. These plains would prove to be the key to Greenfield's prosperity as farmers found them to be endless sources of fertility.

The first permanent structure in the town was a stagecoach station built by Matthew Clark at the corner of West Iowa and SW Second Streets. The building was constructed of native hewn planks with a canvas roof.

The stagecoach, which passed through Greenfield on its way from Des Moines and Winterset to Lewis and Council Bluffs, then known as the Kanesville, was the main form of transportation for travelers through town until the railroad arrived in 1879. With the railroad came not only passenger transportation, but freight service for the area's stock, grain and produce. That first stagecoach station also housed the first post office with Clark as the first postmaster; and the second structure added to the town was the Kirkwood Hotel in 1858. Early ads list the going rate for board and lodging at $2 per night. That included "portable conveniences" but no bath.

After the hotel was built the stage stopped there, and Clark's stage station became Greenfield's first store, opened by A.P. Littleton in 1859. Littleton traveled a two-week journey to St. Louis, Missouri, for his dry goods stock. He later opened the first school and became the first mayor of Greenfield. His home, built in the 1860s at the corner of West Iowa and NW Third Street, still stands as the oldest surviving house in town. It has a native walnut staircase and woodwork. The house served as the first school and city council chamber.

By 1859, the town included two general merchandise stores, a harness shop and a blacksmith.

The first schoolhouse was built in 1861. The first doctor, Dr. Edginton/Edinton, set up practice in 1864. The first lawyer, T.W. Neville, came in 1869. Early doctors pulled teeth, and early lawyers handled real estate transactions. By 1873, Greenfield's business district consisted of three general merchandise stores, a harness shop, two blacksmiths, a drug store and the hotel.

In 1875, Greenfield became the county seat after a heated and protracted battle with neighboring Fontanelle and a courthouse was built on the current site of the Warren Cultural Center. The current Adair County Courthouse was built in 1891. This country's wars have taken their toll on artifacts surrounding the structure. A gazebo on the south lawn was burned during a WWI victory celebration and cannons that once decorated both entrances were melted down during a WWII scrap iron drive.

The year 1875 also saw the introduction of the town's first newspaper. The Greenfield Transcript was printed in an upper room of Littleton's store. The first issue, published July 2, 1875, was an eight-column folio with one side published and printed in Chicago. The Transcript was short-lived, however, and in 1889 E.J. Sidey established the Adair County Democrat. The Democrat later changed its name to the Adair County Free Press and is still published today; still owned and operated by the Sidey family.

Dan Heaton and his wife came to Greenfield sometime prior to 1875. In December of that year, they opened a bank, the Adair County Bank, on the north side of the square. The institution continues today as the Greenfield branch of First National Bank of Fontanelle, Greenfield, Massena, Anita and Correctionville.

The city was incorporated in 1876 with A.P. Littleton as the first mayor and S.E. Vance, Charles Burrell, J.A. Myers, T.J. Shinn and D. Patterson on the first city council.

The first permanent church structure was erected in 1877 by the Methodist congregation.

The bustling town was struck by tragedy in 1883, when fire broke out in the back of J.W. Valentine's bakery on the south section of the east side of the square. The fire was discovered about 5 a.m. An alarm was sounded, but Greenfield at that time had no fire organization or facilities. Fortunately, there was little wind and a light rain was falling. The fire soon spread to the stable behind the bakery, then north to the meat market, the barbershop, the land office, and the courthouse. At the same time, it leaped across the alley south to the stable of the Methodist parsonage. It then moved westward, threatening another entire quarter block of Greenfield businesses. But quick and diligent work of a bucket brigade kept a steady stream of water flowing and only three buildings of the south side of the square were destroyed.

After the fire, the town rebuilt. The courthouse was replaced with one built by the county, not nearly as fine as the city-built structure destroyed by the fire. The building was often referred to as the "sheep shed." A new, grand courthouse was erected in 1896 in the center of the town square. Listed on the National Register of Historic Places, the courthouse remains in use as the center of Adair County government today.

By the end of the 19th Century, Greenfield was a bustling town with a population of 1,200. Businesses lined the square and culture and education were important facets of prairie life. The Greenfield Electric Light Plant began electrifying the town in 1890, one of the few in the state at the time. The lights were on from sundown to 11 p.m. daily, and 5 a.m. to sun-up in the winter. The first local telephone system was established in 1896 with about 20 telephones on the line. Today, Greenfield Municipal Utilities is the third oldest continuously operated municipal utility in Iowa.

It was in this environment, in 1896, that E.E. Warren and his wife, Eva, built the E.E. Warren Opera House and Warren Dry Goods Store on the east side of the Square, on the site of the “sheep shed” courthouse. The three-story structure with its decorative turret has dominated the Greenfield skyline for more than 100 years. In its early years, the Opera House hosted traveling theatrical troupes, medicine shows, musical productions and local theatre. Mrs. Warren was a stanch supporter of the arts and an accomplished musician in her own right. The upper floors of the building gradually declined in usage, but the ground floor remained in use as retail space until 1990. It was placed on the National Register of Historic Places in 1979. In 2012, the Opera House, along with the adjoining Hetherington and Taylor buildings reopened as the Warren Cultural Center, a multi-use center of culture and commerce that includes an auditorium and historic rooms, gallery, and office space including the Adair County ISU Extension and Outreach office. Ed & Eva’s, a retail establishment devoted to the work of Iowa artists, occupies the space created for the Warren Dry Goods Store.

The first move to establish a public library in Greenfield also took place in 1896, but it was not until 1916 that the task was finally accomplished with the help of the Progress Club. It was the women of the town exercising their newly acquired right to vote who made the effort reality. The building on the corner of South First Street and Highway 92 was built for that use with funds provided by the Andrew Carnegie Foundation. The library building remained in use until 1997 when the library and city hall moved into new accommodations across the street. The building housed a gift shop for a time and is now home to the Greenfield Chamber/Main Street and Development office.

The Greenfield Square and eight adjoining city blocks were paved in 1911 and the hitching chain was removed. The following year, about a mile of paved streets were added. By 1955, the city had more than 100 blocks of paved streets. Downtown streets and infrastructure were upgraded in 2007 with the help of the Greenfield Main Street Design Committee.

According to the 1915 History of Adair County, "A visitor to Greenfield will find a town which has had a steady growth without the usual boom. They will find a town whose property has been born by the energy, enterprise and enthusiasm of the west, guided and controlled by the safe conservatism of men of wise perceptions. Greenfield is a thriving little city of wide-awake, enterprising citizens. The business portion of the town never appears dull to the observer. Life and property are valued and well established and maintained, and with good society, healthy and delightful climate, good location of the city as to drainage, railroad, telephone, telegraph and mail facilities, good schools and churches and institutions, living in Greenfield is a decidedly pleasant occupation."

In 1920, a number of Greenfield businessmen built Hotel Greenfield at a cost of $60,000. The building served as a haven for weary travelers arriving in town on rail and bus lines for many years, as was the departure station for local soldiers in WWII. Under private ownership, the lodging portion was gradually abandoned with only the restaurant remaining. In 2011 it was again a group of local investors, ADCO Enterprises, who brought the place back to its former glory with boutique-style lodging and on-site eatery.

The Great Depression and two World Wars took their toll on the tiny community. Still it continued to grow. The country club opened in 1924. A volunteer fire department was formed and a fire truck purchased in 1926. In 1931, natural gas arrived to the town. The public swimming pool, still in use, was built as a WPA project in 1941.

A movement to build a hospital was started by the Greenfield Service Club at the end of WWII. The project was completed in 1950. The facility was renovated in 2008 and today Adair County Health System provides state-of-the-art in- and out-patient services.

The 1950s and 1960s saw a Rockwellian version of American life. Town Night on the square offered a variety of businesses to frequent, a movie to see, a good meal at a small town café, and a snow cone or popcorn from Eddie's Super Popcorn Stand. The Friday night high school football game was the hottest show in town.

In 1969, Hollywood producer Norman Lear discovered Greenfield's charm and used it as the set for his movie "Cold Turkey." Starring Dick Van Dyke, Jean Stapleton, Bob Newhart and Tom Poston, the movie involved a town that accepted a challenge to quit smoking for 30 days. Greenfield also rose to the challenge and went "Cold Turkey" with 166 of its citizens signing Stop Smoking pledges. In 1999, a "Cold Turkey" reunion was held with Lear and several original cast members in attendance.

In 1974, Cardinal Insulated Glass moved into the community and became the largest employer. Siegwerk Inc, an ink processing plant, joined them in the industrial park on the north edge of town in 1981, now QuadGraphics CR\T.

Another major employer in town, Schildberg Construction Company Inc., has been a part of the community since 1937. The family-owned company, which mines 20 limestone quarries throughout Southwest Iowa and Missouri, maintains its corporate headquarters in Greenfield. The Schildberg family has been a generous force, donating private collections to create the Iowa Aviation Museum one mile north of Greenfield and the Dennis and Marlene Schildberg Antique Car collection just east of the Square. Yvonne Schildberg purchased and donated the decaying Opera House for restoration.

Greenfield has hosted RAGBRAI, the Des Moines Register's Annual Great Bicycle Ride Across Iowa, three times in the ride’s history, and added to its cinematic history providing the backdrop for scenes in the movie “Peacock.”

In 1995, Greenfield became affiliated with the Main Street Iowa program and became a Main Street community. The organization offers consultation and expertise in preserving and rejuvenating the downtown area.

The 21st Century has seen a surge of rejuvenation with the downtown streetscape, Hotel Greenfield, Warren Cultural CenterAdair County Health System and a new Adair County Law Enforcement Center that replaces the 1903 jail.

Building on its rich history of resourceful enterprise and community, Greenfield looks forward to the future as the place to be – for Life. for Business. for Fun.

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