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Sip & Savor

The Low Road: The Ward Boss Caucus

Boston · 5 stops · every stop verified in live map data · ends near a bed

The machine that ran Boston was oiled in taverns, and the caucus never really adjourned. Cobblestones, oysters, jazz, and a hotel that named its bar after the whole racket.

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  1. 1 · The Cold Open
    Bell in Hand Tavern
    Opened by the town crier who spent forty years shouting Boston's news and retired to pour its beer. The name honors the bell he carried. Ale first, arguments second, exactly as Jimmy Wilson intended in 1795.
    est. 1795 · from noon · verified Jul 2026
  2. 2 · The Detour
    Green Dragon Tavern
    The Sons of Liberty plotted a tea party in the original around the corner, and Daniel Webster called it the headquarters of the Revolution. This room carries the name and the habit. Order a lager and lower your voice accordingly.
    lineage to 1654 · day into night · verified Jul 2026
  3. 3 · The Anchor
    Union Oyster House
    America's oldest continuously running restaurant. Daniel Webster took a tumbler of brandy with every half dozen oysters at this same curved bar, and JFK kept the upstairs booth. Order the raw dozen and mind the precedent.
    est. 1826 · lunch till evening · verified Jul 2026
  4. 4 · The Wildcard
    Wally's Café
    Joseph Walcott opened it in 1947 and it became one of America's oldest family owned jazz rooms. Berklee kids sit in nightly and leave better. No cover, no nonsense, all horn.
    est. 1947 · sessions nightly · verified Jul 2026
  5. 5 · The Last Call
    The Last Hurrah, Parker House
    The Parker House invented the roll, hosted JFK's proposal dinner, employed Ho Chi Minh in the bakery and Malcolm X in the dining room. The bar is named for the great ward boss novel. One whiskey under the portraits, caucus adjourned, bed upstairs.
    hotel est. 1855 · till late · verified Jul 2026 · 🏨 the night ends at Omni Parker House

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