Winter Wine tours in Ashland, Oregon
Cozy Winter Wine Tours with The Columbia Hotel
Looking for a wine tour in Southern Oregon that feels relaxed, local, and a little bit magical? This winter, The Columbia Hotel is partnering with Ashland Mountain Adventures to offer small-group Winter Wine Tours and shuttles to the best wineries around Ashland, Oregon.
Sip award-winning Rogue Valley wine, let someone else do the driving, and end the day just steps from downtown dining, live music, and the historic charm of The Columbia Hotel.
Why Winter is Perfect for Wine Tasting in Southern Oregon
Southern Oregon is known for sunny vineyard days, but winter is secretly one of the best seasons for wine tours:
Fewer crowds and more personal attention at the tasting bar
Cozy indoor spaces with fireplaces, big windows, and valley views
Rich reds and cool-climate whites that pair beautifully with winter food
Easy access from downtown Ashland – no long highway drives required
Our Winter Wine Tours are designed as 4-hour experiences with 10–14 guests per shuttle, perfect for friends’ getaways, company outings, or pre-theatre adventures.
What’s Included in Our Winter Wine Tour Packages
Each Winter Wine Tour includes:
Round-trip shuttle service with Ashland Mountain Adventures from The Columbia Hotel
Comfortable van seating for 10–14 guests
Visits to 3 carefully selected Ashland wineries (option to add a 4th for custom/private tours)
Time for tastings, photo stops, and bottle purchases at each stop
Local insight and route planning from our team at The Columbia Hotel and Ashland Mountain Adventures
Tasting fees are paid directly to each winery and may vary by flight or experience.
Featured Wineries on Our Winter Wine Routes
We partner with some of the most beautiful and welcoming wineries in the Ashland area, chosen for their great wine, great spaces, and great winter vibes.
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![Weisinger Family Winery Vineyards]()
Weisinger Family Winery – Ashland’s Original Craft Winery
Just a few minutes from downtown, Weisinger Family Winery overlooks Bear Creek Valley with a spacious deck and cozy tasting room. Family-owned since 1988, Weisinger focuses on small-lot wines made from local, sustainably grown grapes within about five miles of the winery.
Expect beautifully made Tempranillo, Syrah, Malbec, Pinot Noir, Viognier, Sauvignon Blanc, Chardonnay, and more – plus friendly hosts and an easygoing atmosphere that’s perfect for your first stop of the day.
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![Irvine & Roberts Winery Tasting Outdoor Seating]()
Irvine & Roberts Vineyards – Cool-Climate Elegance in the Hills
High in the hills just outside town, Irvine & Roberts offers a modern tasting room with floor-to-ceiling views of surrounding vineyards and mountains. Specializing in Pinot Noir, Chardonnay, Rosé, and Pinot Meunier, they lean into a cool-climate, Burgundian style that’s precise, layered, and food-friendly.
This is a favorite stop for guests who really want to talk terroir, soils, and winemaking philosophy while they sip.
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![Dana Campbell Vineyard establishment]()
Dana Campbell Vineyards – Relaxed Ridgeline Views
Perched above Ashland with sweeping valley views, Dana Campbell offers a relaxed, friendly tasting experience. Estate-grown warm-climate varietals like Tempranillo, Malbec, Sauvignon Blanc, Carmenère, and Verdejo show off the Rogue Valley’s sunny side.
On fair winter days, guests can enjoy the view from the patios; on colder days, the indoor spaces and fire features keep things cozy.
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![Belle Fiore Estate & Winery outdoor tasting patio]()
Belle Fiore Estate & Winery – Chateau Views & Old-World Charm
For guests who love a little drama with their tasting, Belle Fiore is a must-see. This European-inspired estate features an Italianate wine pavilion and a French-style chateau with panoramic views of vineyards and the Rogue Valley.
Belle Fiore has won numerous awards for its Pinot Noir, Cabernet Sauvignon, and Merlot-based blends, and they also grow distinctive Mediterranean varieties like Montepulciano, Barbera, Teroldego, Verdejo, and Muscat Canelli dessert wines. It’s as photogenic as it is delicious.
Sample 4-Hour Winter Wine Tour Itinerary
“Ashland Hills & Valley Views” – 3 Wineries
12:00 pm – Depart The Columbia Hotel with Ashland Mountain Adventures
12:10 pm – Tasting at Weisinger Family Winery
1:15 pm – Tasting at Irvine & Roberts Vineyards
2:20 pm – Tasting at Dana Campbell Vineyards
3:30–4:00 pm – Return to The Columbia Hotel, stroll into downtown for dinner or theatre
Actual timing varies by group pace, weather, and winery reservations, but most Winter Wine Tours run about 4 hours door to door.
Custom & Private Winter Wine Tours
Planning a birthday, bachelorette, company outing, or friends’ weekend?
We can help you design a custom wine route with:
Your choice of wineries
Longer time at your favorite stop
Optional add-ons like charcuterie boards, dessert wines, or photo stops
Private tours are ideal for groups of 10–14 guests. Smaller groups can often join shared tours, depending on the date.
Who These Tours Are Perfect For
Couples and friends staying at The Columbia Hotel
Winter visitors looking for more than the ski hill or theatre
Southern Oregon locals wanting a car-free wine day
Corporate or retreat groups based in downtown Ashland
No designated driver needed – your shuttle will pick you up and drop you off right at The Columbia.
How long is the wine tour?
Most Winter Wine Tours are about 4 hours, visiting 3 wineries. Some private groups choose to extend the tour or add a fourth stop.
Do we have to stay at The Columbia Hotel?
Tours are designed to depart from and return to The Columbia Hotel. Guests staying elsewhere in Ashland are welcome to join but must meet the shuttle at the hotel.
Frequently Asked Questions
How many people can the shuttle hold?
Each Ashland Mountain Adventures shuttle holds 10–14 guests, depending on configuration.
Is winter driving safe?
Our tours partner with Ashland Mountain Adventures, a local company experienced with regional roads in all seasons. Routes are chosen with winter conditions in mind.
Are tasting fees included?
Tasting fees are paid directly to each winery and vary by flight or experience. We’ll let you know what to expect when we help you plan your route.
Book Your Winter Wine Tour
Ready to plan your Winter Wine Tour in Ashland, Oregon?
Call The Columbia Hotel front desk at 541-601-2087
Email stay@columbiahotelashland.com with your preferred date, group size, and ideal start time
Or add a note about “Winter Wine Tour” when booking your stay online and we’ll follow up
Let us handle the logistics so you can swirl, sip, and savor Southern Oregon wine all winter long.
Make a night of it and stay at The Columbia Hotel. Contact us for group rates and wine tour packages.