The Top 3 Cocktail Bars Near Jumbo's Win Win

Updated June 17, 2026

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  1. Rank 1. Hazel Hill

    Californian French

    Awards
    Address
    100 Montage Way, Healdsburg, CA · Healdsburg
    Online
    WebsiteInstagram
    On the Way What's Around

  2. Rank 2. The Matheson

    Mediterranean New American

    Dustin Valette's soaring dining room lets seasonal California ingredients and Mediterranean technique speak without artifice, from a silken petrale sole paired with mushroom dashi to foie gras sharpened by kiwi. The kitchen's ingenuity finds its match in a wine program that pours over a hundred selections by the glass.

    Awards
    Address
    106 Matheson St, Healdsburg, CA · Healdsburg
    Reserve
    OpenTable
    Online
    Website
    On the Way What's Around

  3. Rank 3. Little Saint

    Vegetarian

    Awards
    Address
    25 North St, Healdsburg, CA · Healdsburg
    Online
    WebsiteInstagram
    On the Way What's Around

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