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 3

Day 3 Jacksonville to the Applegate Valley


Applegate Valley Wine Country, picnic lunch on the Applegate River at Red Lily Vineyards, wine and cheese tasting at Wooldridge Creek Winery and CrushPad Creamery.

Southern Oregon Wine Country Bicycle Tour elevation map, day 3

Route Details:

Day 3 of the Southern Oregon Wine Country Bicycle Tour takes us to new valley and a new wine region. The Applegate Valley AVA consists of a group of 18 unique wineries producing a diverse array of high quality and hand-crafted wines. This narrow valley is much less populated than the valley we rode yesterday. The mountains are closer and more rugged and the terrain more varied. The scenery is striking. All these attributes make this one of the most interesting wine regions in the west.

Getting there requires a bit of climbing. If you are up to the challenge, you can ride from our hotel in Jacksonville to the summit of Sterling Creek Road. The rest of us will board the van for a relaxing shuttle to the top. Either way, we are all on our bikes for one of the sweetest downhill rides in Southern Oregon. After six miles of smooth pavement, easy curves, and ever changing postcard quality vistas, we glide to a stop at the tiny ghost town of Buncum. From here the route continues on a gradual downhill course past vineyards, organic farms, and small ranches to our picnic lunch stop at Red Lily Vineyards on the banks of the peaceful Applegate River.

Refueled, and perhaps reinvigorated with a sip of Red Lily’s award-winning Tempranillo, we set out on our bikes again to the bucolic North Applegate River Road with row upon row of grape vines stretching from the river’s edge up the hillsides to forest interface zone. From here, stronger riders may want to extend the route with a 14 mile loop to the other side of the valley and rejoin the group at our next destination, the highly acclaimed Wooldridge Creek Winery and CrushPad Creamery. Ah, boutique wine and artisan cheese, how can you beat that? Rest your legs and take in the magnificent views of the valley you just rode through from the veranda of the tasting room.

We have one more treat for you on today’s route. Hop on your bike or our shuttle for a 3 mile, mostly downhill glide to Schmidt Family Vineyards. This beautifully landscaped property is about as close as Southern Oregon gets to a large estate winery. We’ll nosh on appetizers and sample the libations before we load onto the Via Bike Tours van for a shuttle back to Jacksonville. Rest up a bit at the hotel. We have another fabulous dining experience waiting for us this evening.

Day 3 Gallery: