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5 on this page| № | Name | Category | Address | Record |
|---|---|---|---|---|
| 01 | Thee Cake Carpenter Family-run bakery and cafe, home of the Cheesecake Nachos, making custom cakes, cheesecake tacos, and blondie bars. | Bakery | 39 S Main StWinchester, KYWinchester Downtown Commercial District | Listed · independent · address on record |
| 02 | Laura's Mercantile Kentucky Proud farm store selling hemp products, hemp chocolates, grass-fed beef, and organic goods. | Market | 1 S Main StWinchester, KYWinchester Downtown Commercial District | Listed · independent · address on record |
| 03 | The Hall Coffee & Social Club Community-focused coffee shop and cafe on Main Street serving espresso drinks, fine teas, and breakfast and lunch fare. | Coffee Shop | 17 S Main StWinchester, KYWinchester Downtown Commercial District | Listed · independent · address on record |
| 04 | Abettor Brewing Company Winchester's hometown craft brewery with a taproom in a converted downtown building just off Main Street. | Brewery | 128 N Highland StWinchester, KYWinchester Downtown Commercial District | Listed · independent · address on record |
| 05 | Loma's at the Opera House Upscale-casual dinner spot established 2018 in the historic Winchester Opera House building. | Restaurant | 103 S Main StWinchester, KYWinchester Downtown Commercial District | Listed · independent · address on record |