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5 on this page| № | Name | Category | Address | Record |
|---|---|---|---|---|
| 01 | Mundy's Asia Galleries Independently owned gallery specializing in Asian antiques and art, located on Main Street in the village center. | Gallery | 35 Main StStockbridge, MAMain Street Historic District | Listed · independent · address on record |
| 02 | The Red Lion Inn Historic 18th-century inn and tavern anchoring Main Street, a Berkshires landmark since the 1770s, with dining rooms and a taproom. | Restaurant | 30 Main StStockbridge, MAMain Street Historic District | Listed · independent · address on record |
| 03 | Elm Street Market & Tiffany's Cafe Locally owned general store and attached cafe/deli in the village center, open daily for groceries, sandwiches, and breakfast/lunch fare. | Market | 4 Elm StStockbridge, MAMain Street Historic District | Listed · independent · address on record |
| 04 | Stockbridge Coffee & Tea Combined cafe and used bookstore on Elm Street serving espresso, pastries, and light fare, with art by local artists on the walls and regular readings. | Coffee Shop | 6 Elm StStockbridge, MAMain Street Historic District | Listed · independent · address on record |
| 05 | Once Upon a Table Intimate bistro-style restaurant operating since 1996, known for seasonal, hand-crafted American cuisine in a casual-but-refined setting on Main Street. | Restaurant | 36 Main StStockbridge, MAMain Street Historic District | Listed · independent · address on record |