Munger is responsible for the design of Greenfield's unique Lancaster-style town square, and the city park located at Grant and NE Second Street was also included in the original plat.

Well-known White House reporter forTime/Life and author Hugh Sidey (1927–2005), brother of Edwin J., was also closely associated over time with the family's journalism and photojournalism legacies.

Publisher/Editor Linda E. Sidey, widow of Edwin J., relocated the newspaper business and its associated photo gallery to 141 Public Square in December 2010.

[11] According to the United States Census Bureau, the city has a total area of 1.81 square miles (4.69 km2), all land.

In 1995, Greenfield became affiliated with the Main Street Iowa program, to rejuvenate the downtown area.

The Main Street Approach was developed by the National Trust for Historic Preservation's National Main Street Center with the goal of economic development within the context of historic preservation.

[18] Greenfield's unique Courthouse, built in Romanesque style and listed on the National Register of Historic Places in 1981, was constructed in 1891 after the original was destroyed in a fire.

Mr Hetherington was simultaneously building his new store alongside the E. E. Warren Opera House.

In the early years, the Opera House hosted traveling theatrical troupes, medicine shows, musical productions and local theatre.

In 1996, the E. E. Warren Opera House Association was formed to save and restore the building and its integrity.

The association has made numerous structural and aesthetic improvements to the interior and exterior of the building.

There will be retail and dining space to enhance the visitor's experience and the facility aims to support live theatre performances, concerts, art exhibits and many more entertaining events.

Many early hotel patrons traveled to town by the C, B & Q freight-passenger train and were shuttled from the south Greenfield depot.

Despite the shadow of the Great War (WW I) local boosters were yet able to capitalize a 32-room state-of-the-art lodge at a cost of $65,000.

Regional architect William Gordon designed the Classical Revival (Commercial) style building, to be constructed starting in 1919.

A gala Grand Opening was featured June 3, 1920, with William Don Carlos and George Musmaker toastmasters of the evening.

The original “Greenfield Hotel Company” of April 8, 1919, was founded by local business owners and town boosters as a community improvement project, more than as a profit-making enterprise, as such.

Lawyer George Musmaker, president, and banker Jay Howe, secretary-treasurer, were two of the company's primary leaders during those first 32 years.

Beginning in 1999, Ray "Bubba" Sorensen II has painted the rock every Memorial Day with different patriotic images and sayings in support of the United States military.

Located on the west edge of Greenfield, it is operated by the Adair County Historical Society Archived February 17, 2012, at the Wayback Machine.

After remodeling an old Ford dealership building, he was able to house his cars and display them for the public to enjoy.

Ken Sidey Nature Area is owned by the Adair County Conservation Board.

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.

Portions of the 2009 thriller Peacock were filmed in Greenfield and other towns in Adair County.