All states›Oregon›Winston

Wineries & Breweries in Winston, OR

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

Winston has about 5,691 residents, which works out to 53 wineries & breweries per 100,000 people. Population: U.S. Census Bureau, 2024 estimate.

Wineries & Breweries in Winston

The most complete and owner-verified listings first — hours, phone, website, services. No pay-to-play.

  1. Freed Estate Vineyard

    430 Hooten Rd, Winston, OR 97496-9689

    Thu-Sun 1-5pm

    TastingsOutdoor seating
  2. Wild Rose Vineyard

    375 Porter Creek Rd, Winston, OR 97496

  3. Lookingglass Brewery

    192 SE Main St, Winston, OR 97496

3locations
53per 100,000 residents
3with a phone
2with a website
1publish hours

Of the 3 wineries & breweries listed in Winston, 3 give a phone number, 1 publishes opening hours and 2 have a website. The nearest bigger selection is Roseburg with 31.

Winston 3 locations

More locations within 30 miles of Winston

Only 3 locations listed in Winston itself, so here are the closest ones in nearby towns. Distance is straight-line from Winston.

  1. Abacela Winery

    2.6 mi · 12500 Lookingglass Rd, Roseburg, OR 97471-9067

    Daily 11am-6pm

    TastingsToursFood servedOutdoor seatingPrivate events
  2. Pyrenees Vineyard & Cellars

    3.6 mi · 15332 Old Highway 99 S, Myrtle Creek, OR 97457-8603

  3. Spangler Vineyards

    3.9 mi · 491 Winery Ln, Roseburg, OR 97471-9365

    Thu-Mon 11am-6pm

    TastingsPrivate events
  4. Draper Brewing

    6.2 mi · 7752 Highway 42, Tenmile, OR 97481

  5. Girardet Wine Cellar

    8.1 mi · 895 Reston Rd, Roseburg, OR 97471-8611

  6. Trella Vineyards

    8.4 mi · 646 SE Jackson St, Roseburg, OR 97470

    Tue-Sat 12-7pm

    Tastings
  7. Draper Brewing

    8.4 mi · 640 SE Jackson St, Roseburg, OR 97470

  8. Paul O'Brien Winery

    8.4 mi · 609 SE Pine St, Roseburg, OR 97470-3146

Guides for location shoppers

All guides

Oregon statewide, by feature

Nearby in Oregon

Good to know about wineries & breweries in Winston

How many wineries & breweries are there in Winston?

We list 3 wineries & breweries in Winston with addresses, and 3 of them with a phone number.

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

Call ahead — 3 of the 3 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.

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 3 tasting venues in Winston, Oregon, with 3 listed with direct contact details to confirm dress code policies.

What to wear on a wine tour?

Dress in comfortable layers and wear closed-toe flat shoes suitable for cellar floors and outdoor vineyard walking. Bring a light jacket or sweater, as wine cellars are kept cool year-round. Check out 3 wine tour providers in Winston, Oregon, including 3 that offer phone assistance for tour planning.