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 4

Day 4 Jacksonville to Gold Hill


Rogue River Greenway, Del Rio Vineyards, Rogue Creamery, Lily Belle Farms Chocolate Factory, Ledger David Cellars Tasting Room, Oregon Shakespeare Festival Play.

Southern Oregon Wine Country Bicycle Tour elevation map, day 4

Route Details:

We ride the upper Rogue Valley wine region on our final day of the Via Bike Tours Southern Oregon Wine Country Bicycle Tour. Bidding farewell to Jacksonville we head north out of town and into horse country. Our route hugs the foothills, providing us with grand valley vistas and the distant volcanic peak of Mt. McLoughlin. Before long we begin a downhill course that connects us with the mighty Rogue River. A few miles downstream, we cross the river at a popular salmon fishing spot and meander our way back upstream on a gorgeous bike path through Valley of the Rogue State Park. A quick 3 miles later, we arrive at Del Rio Vineyards and Winery for a delicious picnic lunch in the manicured garden that surrounds the property’s historic tasting room.

Our standard route ends here, but we still have a full day of excitement ahead. If you still have your wits about you and strength in your legs, consider riding to our next destination, the “Artisan Corridor.” Non-riders will board the Via Bike Tours van for a shuttle to this wonderful spot that features a trifecta of foodie delights  – Lily Belle Farms Chocolate Factory, Ledger David Cellars, and the internationally acclaimed Rogue Creamery. Wine, cheese, and chocolate. Say no more!

Ah, but there is more. We board the van for a shuttle back to Ashland, checking back into the Plaza Inn & Suites in time to rest and freshen up a bit before we regroup for our last and very special evening together. It begins with another fabulous fine dining experience. Then we top off the evening with a play presented by the Tony Award winning Oregon Shakespeare Festival.

Day 4 Gallery: