Retail is a very important factor to the economy of Oskaloosa. This volume of retail is usually only found in communities twice this size. The Oskaloosa Area Chamber & Development Group works hard to grow and strengthen the Oskaloosa retail community. The Chamber has conducted an ongoing program since 1997, called the "Oskaloosa First" campaign. This campaign uses a daily newspaper and a radio station to encourage local residents to do their shopping locally.

There are also numerous retail promotions during the year. Some of these promotions include: the annual Business Festival,

Art on the Square, the 4th of July Stock Car Races, Ridiculous Days, Sweet Corn Serenade and Craft Show, Holiday Open House, Lighted Christmas Parade, Business After Hours events, small business seminars and more than 80 special events sponsored by the Chamber Diplomats. These diplomats are the Chamber’s meeters and greeters.

Oskaloosa, which is served by four arterial highways, is the "retail hub" of the county and the region with an estimated trade area population of 44,474. There are four primary retail centers in Oskaloosa. These centers are:

1. Heartland Square and surrounding area east of town houses. Heartland Square consists of 5 retailers, including Wal-Mart.

2. Historic downtown, which is listed on the National Register of Historic Places, is the home for 32 specialty shops, along with many service businesses.

3. Penn Central Mall, which is connected to the downtown, is where many major retailers are housed. These retailers include JC Penney’s, Bath and Body Works, GNC, Claire’s Boutiques, Brass Buckle, Radio Shack, Hallmark plus 10 other retailers.

4. "A" Avenue businesses include craft shops, a major drug store, and Sears. Here are also many auto part stores, convenience stores and four grocery stores (HyVee, Fareway, Econo Foods and Aldi's).

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