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5 on this page| № | Name | Category | Address | Record |
|---|---|---|---|---|
| 01 | Bardavon 1869 Opera House The oldest continuously operating theater in New York State, a 944-seat 1869 opera house on the National Register of Historic Places that hosts live music, dance, opera, and comedy just off Main Street. | Live Music | 35 Market StPoughkeepsie, NYMain Street Historic District | Listed · independent · address on record |
| 02 | Cryptic Gallery An independent art gallery and community hub on Main Street showcasing work by local and regional artists, including murals and rotating exhibitions. | Gallery | 358 Main StPoughkeepsie, NYMain Street Historic District | Listed · independent · address on record |
| 03 | The Poughkeepsie Grind A locally owned coffeehouse on Main Street that roasts its own beans in-house under its Illuminated Coffee Company label, serving espresso drinks and light fare. | Cafe | 107 Main StPoughkeepsie, NYMain Street Historic District | Listed · independent · address on record |
| 04 | Mill House Brewing Company A brewery and restaurant just off Main Street serving an extensive food menu of pizza, burgers, pasta, and fish alongside a wide draft list, with regular Sunday brunch and happy hour. | Restaurant | 289 Mill StPoughkeepsie, NYMain Street Historic District | Listed · independent · address on record |
| 05 | Zeus Brewing Company A craft brewpub in the Union Street Historic District section of Main Street, pouring house-made beers alongside a full pub food menu in a renovated historic storefront. | Bar | 178 Main StPoughkeepsie, NYMain Street Historic District | Listed · independent · address on record |