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5 on this page| № | Name | Category | Address | Record |
|---|---|---|---|---|
| 01 | DaVallia (39 North Gallery) An art gallery and boutique established in 2009, showing work in wood, glass, metal, pottery, and jewelry from more than 60 regional and national artists. | Gallery | 39 North StChester, VTChester Village Historic District (Main Street / The Common) | Listed · independent · address on record |
| 02 | Alder Bakery & Eatery A cafe and bakery serving coffee, pastries, breakfast, and lunch. | Bakery | 642 VT-103Chester, VTChester Village Historic District (Main Street / The Common) | Listed · independent · address on record |
| 03 | Chester Bookworm A used, rare, and antiquarian bookshop specializing in nonfiction and European titles, with an on-site bookbinding and restoration workshop. | Bookstore | 330 Main StChester, VTChester Village Historic District (Main Street / The Common) | Listed · independent · address on record |
| 04 | Meditrina Wine & Cheese A wine, beer, and cheese shop and bar on Main Street offering tastings and a curated retail selection. | Bar | 295 Main StChester, VTChester Village Historic District (Main Street / The Common) | Listed · independent · address on record |
| 05 | Country Girl Diner A genuine 1944 Silk City dining car serving breakfast and lunch with daily-changing pies and baked goods, in its Chester location since 1966. | Restaurant | 46 VT-103 SouthChester, VTChester Village Historic District (Main Street / The Common) | Listed · independent · address on record |