Southern Oregon Wine Country Bicycle Tour

2016 TOUR DATES:  AUG 31 - SEP 3 (Closed)
Contact us about future tour dates

  • Southern Oregon Wine Country Bicycle Tour


Stunning Landscapes • Vineyards • Orchards • Small Farms • Award Winning Wines • Farm-To-Fork and Wine Pairing Dinners • Boutique Wineries • Artisan Cheese and Chocolate • Oregon Shakespeare Festival Play


  • Difficulty: Easy to Moderate
  • Duration: 4 days, 4 nights
  • Price: $1,400 double occupancy, $410 single supplement
  • Price Includes: 4 nights lodging, 4 breakfasts, 3 lunches, 4 dinners, snacks, luggage transport, support van, guides, 1 Oregon Shakespeare Festival play. Wine tasting fees are not included.
  • Tour Start/End: Ashland, Oregon
  • Overnights: Ashland (2 nights), Jacksonville (2 nights)
  • Nearest Airport: Medford, Oregon (MFR) – we will shuttle you to and from the Medford Airport


Southern Oregon Wine Country Bicycle Tour mileage table


Southern Oregon Winery Bicycle Tour route map

Southern Oregon is a stunning landscape of small fertile valleys parted by wild, iconic rivers and framed by the grand mountain ranges of the Siskiyou and Cascades. Not only does this make an amazingly scenic setting for cycling, but the diversity of geography and microclimates provide a perfect venue for growing award-winning wines in a surprising number of varietals.

“Wine Country the way it used to be.”
–Sunset Magazine

Southern Oregon’s Wine Country is full of peaceful backcountry roads. You won’t encounter the palatial estate vineyards or crowds of tourists that dominate more famous wine regions. As you visit tasting rooms, the person pouring your wine may also be the grower and vintner. This is a region of boutique wineries, small organic farms, artisan food producers, and farm-to-table restaurants. Premier theater, music, and arts opportunities abound in communities that reflect the rich history of Native American tribes, Oregon Trail pioneers, and gold rush prospectors.

Our Southern Oregon Wine Country Bicycle Tour is for cyclists who prefer a relaxed pace on the bike, followed by a tour for the taste buds. The emphasis is on cycling, but each day’s journey takes you to a distinctive end of ride destination to sample fine wines and artisanal delectables. Plus we overnight in two unique, historic, and charmingly festive towns and we close the tour with a play at the Tony Award Winning Oregon Shakespeare Festival.

This is undiscovered wine country. Come and enjoy it before the word gets out.

Southern Oregon Wine Country Bicycle Tour – Day 1

Day 1 Ashland Loop


Bear Creek Greenway, chocolate tasting, orchards, vineyards, expansive valley views, Paschal Winery, wine pairing dinner, Ashland

Southern Oregon Wine Country Bicycle Tour elevation map, day 1

Route Details:

Our Southern Oregon Wine Country Bicycle Tour begins with an early afternoon group get-together in the vibrant town of Ashland, Oregon. After brief introductions, a safety talk, and bike fitting, we start our tour with a ride along a bike path through Ashland to an optional stop at the Dagoba Organic Chocolate factory. Slide up the the free sampling bar to experience a wide variety of exceptionally tasty pure and exotic organic chocolates. If you decide to make a purchase, don’t fret about carrying it with you. Via Bike Tours will deliver your chocolate to your hotel room for you. This policy applies to any wine or food purchases at any point during our tour.

Energized from our chocolate experience, we ride out of town into rural farmland before looping back through Ashland’s quaint railroad district and onto the Bear Creek Greenway. We meander along this paved and shady path as we follow Bear Creek downstream out of Ashland. Before long, we leave the Greenway for our approach to Paschal Winery & Vineyard, our destination winery of the day. Those wishing to continue this blissful ride can opt for an 11-mile extension loop through rural farmland, orchards, and vineyards before reconnecting with the group at the winery.

Now it is time to relax and enjoy your wine and complementary hors d’oeuvres. Get to know your new companions while absorbing the breathtaking valley views. The Via Bike Tours shuttle will take you back to our hotel, the Plaza Inn & Suites at Ashland Creek, for a little downtime before we head out to a delicious wine pairing dinner.

Our day together concludes with dinner. However, if you still have the energy, Ashland has a number of great wine bars, brewpubs, cafes, theaters, and late night music venues to experience. Consider a stroll through delightful Lithia Park, visit an art gallery, or do some window shopping along the vibrant Plaza and Main Street strip. Allow yourself to be mesmerized by this charming mountain town.

Day 1 Gallery: