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 2

Day 2 Ashland to Jacksonville


Bear Creek Valley Wine Country, miles of vineyard and orchard roads, historic “old west” Jacksonville, abundant wine sampling opportunities, farm-to-fork dinner.

Southern Oregon Wine Country Bicycle Tour elevation map, day 2

Route Details:

On Day 2 of the Southern Oregon Wine Country Bicycle Tour we ride from Ashland to the old-west gold rush town of Jacksonville. Sleep in a bit this morning, or grab a cup of locally roasted coffee and walk the town, or visit one of the many nearby spas for some pampering. We will meet late morning for a route discussion followed by a tasty lunch. Then we mount our bikes and pedal off toward Jacksonville.

Today’s route winds through the picturesque vineyards and orchards of the lower Bear Creek Valley, the southernmost portion of the Rogue Valley AVA (American Viticulture Area). Tasting rooms and u-pick farms will tempt us as we meander about the rolling countryside and foothills that are reminiscent of Tuscany. Of course, we won’t experience medieval walled cities on this tour, but we do end today’s route in a town designated as a National Historic Landmark. We are in gold rush country and Jacksonville’s storybook main street reflects the rugged frontier life of the 1850s. We will arrive with plenty of time to explore the dwellings and storefronts that were built to support the gold rush prospectors. These historic buildings now house boutique and antique shops, a few genuine taverns, and some fabulous restaurants.

Wine is the new gold for this region and there are two tasting rooms, Quady North and South Stage Cellars, in the heart of this quaint little town. Stop in for a sip of liquid gold. The Wine Country Inn, our lodging for the next two nights, is only a short distance from downtown. For those who imbibe in the delights of our local vintners or for those who would otherwise prefer not to ride the last few blocks, Via Bike Tours will gladly shuttle you to the hotel.

Tonight we have a special treat for our evening meal. It is a farm-to-fork dinner experience at one of the premier restaurants in town.

Day 2 Gallery: