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Wineries & Breweries in Winchester, VA

20 locations in and around Winchester, Virginia — call ahead or check hours before the drive — many small wineries and taprooms pour only Thursday through Sunday, and harvest season can change everything.

Winchester has about 27,800 residents, which works out to 72 wineries & breweries per 100,000 people. Population: U.S. Census Bureau, 2024 estimate.

Top 10 wineries & breweries in Winchester

Ranked by how complete and owner-verified the listing info is — hours, phone, website, services. No pay-to-play.

  1. 1James Charles Winery

    4063 Middle Rd, Winchester, VA 22602-2594

    Mon-Thu 12-6,Fri 12-8,Sat 12-7,Sun 12-5

    TastingsFood servedOutdoor seatingPrivate eventsDog friendly
    Call Website Directions

  2. 2Wine Mill

    135 Featherbed Ln, Winchester, VA 22601

    Tue-Sat 11am-7pm, Sun 12pm-5pm

    Private events
    Call Website Directions

  3. 3Old Town Cidery

    326 N Cameron St, Winchester, VA 22601-6052

    Fri 3-9pm, Sat 1-9pm, Sun 1-6pm

    Private events
    Call Website Directions

  4. 4Three Wives Distillery

    933 Barley Lane, Winchester, VA 22602

    Saturday – 1 PM – 9 PM, Sunday – 1 PM – 5 PM

    Tours
    Call Website Directions

  5. 5Broken Window Brewing Company

    14 W Boscawen St, Winchester, VA 22601

    Thu 4pm-10pm, Fri 4pm-11pm, Sat 1pm-11pm, Sun 2pm-8pm

    Call Website Directions

  6. 6The Wine Room at Taylor Pavilion

    120 N Indian Alley, Winchester, VA 22601

    Mon-Thu 4pm-10pm, Fri 4pm-12am

    Call Website Directions

  7. 7Winchester Brew Works

    320 N Cameron St, Winchester, VA 22601

    Mon-Thu 4pm-9pm, Fri-Sat 2pm-10pm, Sun 2pm-6pm

    Call Website Directions

  8. 8Vibrissa Beer

    10 N Kent St, Winchester, VA 22601

    Mon-Thu 11am-9pm, Fri-Sat 11am-11pm, Sun 11am-9pm

    Call Website Directions

  9. 9Dividing Creek Beer Co

    160 N Loudoun St, Winchester, VA 22601

    Sun 12am-8pm

    Call Website Directions

  10. 10Alesatian Brewing Co.

    21 & 23 N Loudoun St, Winchester, VA 22601

    Call Website Directions
20locations
72per 100,000 residents
20with a phone
18with a website
9publish hours

Of the 20 wineries & breweries listed in Winchester, 20 give a phone number, 9 publish opening hours and 18 have a website. The nearest bigger selection is Richmond with 99.

Wineries & Breweries in Winchester by feature

Winchester 20 locations

All 10 other wineries & breweries in Winchester

Same order: the most complete listings first.

  1. Escutcheon Brewing Co.

    142 W Commercial St, Winchester, VA 22601

    Call Website Directions

  2. CRUSH Wine Bar Ltd.

    3031 Valley Ave, Winchester, VA 22601

    Call Website Directions

  3. Briedé Family Vineyards

    450 Green Spring Rd, Winchester, VA 22603-2742

    Call Website Directions

  4. Winchester Ciderworks

    2504 N Frederick Pike, Winchester, VA 22603-4162

    Call Website Directions

  5. Virginia ABC

    380 Gateway Dr, Winchester, VA 22603

    Call Website Directions

  6. Virginia ABC

    241 Kernstown Commons Blvd Unit 5F, Winchester, VA 22602

    Call Website Directions

  7. Virginia ABC

    160 Rivendell Ct, Winchester, VA 22603

    Call Website Directions

  8. Virginia ABC

    159 Market St, Winchester, VA 22603

    Call Website Directions

  9. D'Vine Wines

    3103 Valley Ave Ste 104, Winchester, VA 22601

    Call Directions

  10. Sante

    233 Kernstown Commons Blvd, Winchester, VA 22602

    Call Directions

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Good to know about wineries & breweries in Winchester

How many wineries & breweries are there in Winchester?

We list 20 wineries & breweries in Winchester with addresses, and 20 of them with a phone number.

What's the surest way to check hours in Winchester?

Call ahead — 20 of the 20 wineries & breweries here list a number. Hours at independent wineries & breweries shift with seasons and staffing, so a phone call beats any listing, including ours.

Which wineries & breweries in Winchester show their opening hours?

9 of the 20 wineries & breweries we list in Winchester publish their hours — the rest are best reached by phone before you go.

What to wear wine tasting?

Smart casual attire is recommended, such as dark clothing to avoid stain visibility and comfortable flat shoes for walking on gravel or lawns. Avoid heavy perfumes as they interfere with the subtle aromas during a tasting. You can browse 20 tasting venues in Winchester, Virginia, with 20 listed with direct contact details to confirm dress code policies.