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5 on this page| № | Name | Category | Address | Record |
|---|---|---|---|---|
| 01 | Prairie Pearl Boutique Women's clothing and gift boutique listed with the local area Chamber of Commerce. | Boutique | 201 Monroe StreetWinner, SDDowntown Winner (Main Street) | Listed · independent · address on record |
| 02 | Pheasant Bar Local Main Street bar established 1985, known for cold beer, darts, pool, and jukebox. | Bar | 218 S Main StWinner, SDDowntown Winner (Main Street) | Listed · independent · address on record |
| 03 | Shirley's Diner Small, humble-looking diner with generous portions, serving chicken fried steak, patty melts, and biscuits and gravy. | Restaurant | 142 E 2nd StWinner, SDDowntown Winner (Main Street) | Listed · independent · address on record |
| 04 | Huckleberry's Locally owned breakfast-and-brunch spot known for huckleberry pancakes and breakfast burritos. | Restaurant | 886 E Hwy 44Winner, SDDowntown Winner (Main Street) | Listed · independent · address on record |
| 05 | Winner Bakery & Deli Longtime local bakery on Main Street known for its 'Long Johns,' home-baked breads, donuts, and cakes. | Bakery | 237 S Main StWinner, SDDowntown Winner (Main Street) | Listed · independent · address on record |