Wineries in Freeport


Select Local Merchants

  • Massbach Ridge Winery
    Travelers follow Jo Daviess County's sprawling fields and undulating hills toward Massbach Ridge Winery’s 18+ acre estate. Founded by the Harmston family in 2003, the winery’s proprietors grow the grapes to concoct their batches of reds and whites. Members of the winery family escort guests on impromptu tours before rendezvousing in the tasting room or on the patio for samplings. The outdoor patio grants a heightened view of the vineyards below, which visitors can wander through on quests for vine-ripe copies of The Grapes of Wrath. In addition to its frequent tastings and tour sessions, Massbach Ridge Winery hosts a number of wine-related events each year.
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    8837 S Massbach Rd.
    Elizabeth, IL US
  • Hailey's Winery
    A shared dream of Cheryl Hailey and her late husband, Jim, Hailey's Winery began as a mere half acre of grapes planted at the couple's home. The adventure started with homemade wines—specifically, four varietals the Haileys crafted and shared with their friends. What began as a family affair has become a team of women working together to share our labor of love. Now Hailey's Winery is female-owned and producing handcrafted varietals that number a dozen. At the tasting room, visitors can sip samples of the semi-sweet Rocking Chair Red, the dry Timeless White, or the Road Trip Red, which pairs well with meats and books by Kerouac.
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    114 South Franklin Street
    Byron, IL US
  • Northleaf Winery
    Situated inside a renovated historical building, Northleaf Winery pays tribute to the location’s agricultural past while bottling more than a dozen wines. Fragrant samples of peppery zinfandel and floral pinot grigio are poured at the wooden tasting bar, which hosts open tastings and private pairings of wine and artisanal chocolates or cheese. Next door, the bistro and market stocks a tempting selection of Wisconsin cheeses and party trays, along with fresh salads and build-your-own grilled sandwiches with included blueprints.
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    232 S Janesville St.
    Milton, WI US
  • Prairie State Winery
    Your next meal awaits at Prairie State Winery in Genoa. Prairie State Winery is located near endless parking options, allowing diners to find quick and easy parking. Want top-notch taste for less than top-dollar prices? Prairie State Winery's mid-range cuisine is sure to satisfy on both fronts, where pennies stretch into perfectly seasoned platters.
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    217 W Main St
    Genoa, IL US
  • Jamie's Wine Studio
    Come hungry and leave happy! Jamie's Wine Studio in Galena aims to please even the pickiest eater. Parking by the restaurant is a breeze, so feel free to bring your own set of wheels. Bike parking is also available outside the restaurant. Prices at Jamie's Wine Studio are moderate — most diners plunk down about $30 per meal.
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    209 S Main St
    Galena, IL US
  • Acquaviva Winery -
    Picturesque rows of vines and trellises blanket Acquaviva Winery's 40-acre estate. But this idyllic outdoor setting is hardly the only draw. In fact, it may even be overshadowed by the elegant edifice standing nearby. That would be Acquaviva's tasting room, full service restaurant, and marketplace. This structure, whose architecture and decor are the work of artist Andrew Zabela, features the rich color palette and complexity associated with the high Renaissance. Domed ceilings display elaborate, gold-painted plaster filigrees, which, in turn, frame Zabela's hand-painted murals. The elaborateness of the decor actually stands in stark contrast to the simplicity of the wines. "We have a minimal intervention approach to our process," says wine maker Sergio Benavides, "permitting our terroir, grapes, and vines to speak for themselves." He manages every acre of the vineyards, coaxing flavor from 23 different varieties of grapes. His care and tending pay off: virtually every bottle of wine the vineyard produces, from the Bianco Bello to the Frontenac, boasts multiple awards and notes of robust self-esteem.
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    47W614 Route 38
    Maple Park, IL US

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