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5 on this page| № | Name | Category | Address | Record |
|---|---|---|---|---|
| 01 | Fiddlehead at Four Corners Contemporary craft and fine-art gallery (21+ years) housed in the historic First National Bank building, featuring handmade ceramics, glass, jewelry, and paintings. | Gallery | 338 Main StBennington, VTDowntown Bennington Historic District | Listed · independent · address on record |
| 02 | Madison Brewing Company Pub & Restaurant Bennington's first brewpub (est. early 1990s) in a converted downtown storefront, known for DownTown IPA and Old 76 Strong Ale. | Brewery | 428 Main StBennington, VTDowntown Bennington Historic District | Listed · independent · address on record |
| 03 | The Bennington Bookshop Vermont's oldest independent bookstore, established 1928; carries new and used books plus cards and gifts. | Bookstore | 109 South StBennington, VTDowntown Bennington Historic District | Listed · independent · address on record |
| 04 | South Street Cafe & Bakery Longstanding cafe and bakery operating since 1994, known for fresh-baked pastries, soups, and breakfast/lunch fare. | Bakery | 105 South StBennington, VTDowntown Bennington Historic District | Listed · independent · address on record |
| 05 | 421 Craft Bar and Kitchen Locally owned downtown spot blending elevated pub fare with regional craft beers and classic cocktails. | Restaurant | 421 Main StBennington, VTDowntown Bennington Historic District | Listed · independent · address on record |