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Kirk Drake
May 19, 2024 | Kirk Drake

Ashland Oregon Biker Guide to Wineries

Ashland, Oregon Biker’s Guide to Wine Tasting

Discover the perfect blend of cycling and wine tasting in Ashland, Oregon. Whether you’re looking for a leisurely ride, a challenging adventure, or a scenic downhill cruise, these bike routes offer breathtaking views, invigorating exercise, and some of the region’s finest wines.

Ride 1: Leisurely Vineyards Tour

Route: Long Walk Vineyards to Resistance Wine Company to Weisinger’s Winery

  • - Distance: 8.9 miles
  • - Elevation Gain: 469 feet up, 299 feet down
  • - Difficulty: Mostly flat, easy ride

Ashland Oregon Wineries By Bike MapStart your journey at Long Walk Vineyards, where you can enjoy a delightful tasting of their artisanal wines. Once you’ve savored the first round, hop on your bike and set off towards your next destination.

The ride to Resistance Wine Company is a gentle 8.9-mile journey through Ashland’s picturesque landscapes. With only 469 feet of elevation gain and 299 feet of descent, the route is mostly flat, making it perfect for a relaxing ride. Enjoy the scenic views of rolling vineyards and lush greenery as you pedal along.

At Resistance Wine Company, treat yourself to a tasting of their bold and distinctive wines. Afterward, continue your ride to Weisinger’s Winery, your final stop. Here, you can unwind and savor a selection of handcrafted wines while soaking in the stunning views of the surrounding countryside. This ride offers a perfect mix of light exercise, epic vistas, and three exceptional wine tastings.

Ride 2: Challenging Loop for E-Bikes or Adventurous Riders

Route: Eliana Wines to Pompadour and Pilot View Loop to Resistance Wine Company to Weisinger’s Winery to Irvine & Roberts Vineyards

  • - Distance: 11.1 miles
  • - Elevation Gain: 833 feet up, 799 feet down
  • - Difficulty: Moderate to challenging

Ashland Wine Tasting Room Map BikeFor those seeking a bit more adventure or want to get your money’s worth out of that e-bike, this route offers a thrilling blend of challenges and rewards. Start at Eliana Wines, where you can kick off your day with a tasting of their elegant wines.

Next, tackle the loops around Pompadour and Pilot View. These sections of the ride provide a bit of a workout, there is a short track that is about a mile and has a couple hundred feet of elevation to be gained.  Get ready for the Tour de France with this one.  The overall treck (without the loop) has 833 feet of elevation gain and 799 feet of descent, but the views are well worth the effort. The rolling hills and panoramic vistas make for an unforgettable cycling experience.

After conquering the loops, head over to Resistance Wine Company for a well-deserved break and another tasting of their robust offerings. From there, make your way to Weisinger’s Winery to enjoy more exquisite wines amidst beautiful surroundings.

Finally, cap off your ride at Irvine & Roberts Vineyards. This final stop offers not only outstanding wines but also a chance to relax and reflect on the day’s adventure. With 11.1 miles of riding, this route is perfect for those who want a bit more challenge and enjoy the thrill of an electric bike or a vigorous pedal.

Ride 3: Scenic Downhill Cruise

Route: Resistance Wine Company to Sound and Vision

  • - Distance: 6.1 miles
  • - Elevation Gain: 72 feet up, 318 feet down
  • - Difficulty: Easy, downhill ride

Ashland Oregon Winery MapFor a more relaxed and scenic ride, start at Resistance Wine Company. Enjoy a tasting of their distinctive wines before embarking on a 6.1-mile downhill cruise. This route is almost entirely downhill and follows the beautiful Bear Creek Bike Trail, providing a scenic path that’s mostly off major roads.

The gentle descent features only 72 feet of elevation gain and 318 feet of descent, making it an easy and enjoyable ride. Along the way, you’ll experience the tranquil beauty of Bear Creek and its lush surroundings.

Your destination is Sound and Vision, where you can unwind and celebrate the end of your ride. This easy, downhill route is perfect for those looking to combine a leisurely bike ride with scenic views and a delightful wine-tasting experience.


Whether you prefer a leisurely vineyard tour, a challenging e-bike loop, or a scenic downhill cruise, Ashland, Oregon offers the perfect bike routes for wine enthusiasts. Each ride promises stunning scenery, invigorating exercise, and exceptional wine tastings. So, grab your bike, choose your route, and embark on an epic journey through Ashland’s beautiful wine country. Cheers!


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