If you’ve never been to Oregon wine country before, we have good news: You don’t need to be a seasoned sommelier or own a collection of monogrammed wine keys to enjoy this world-renowned region. Simply put: Dundee is as welcoming as it is beautiful. So whether you’re sipping your first Pinot Noir or just looking for a weekend that blends wine with wonder, we’ve put together the perfect three-day itinerary for first-time visitors.
Bonus: Everything listed here is less than a 20-minute drive from The Dundee Hotel—your stylish, centrally located home base for all your wine-fueled adventures.
Note: Wine tasting can sneak up on you, so plan for small bites throughout the day. We also recommend using rideshares or taxis when making multiple tasting stops, and the front desk team at The Dundee Hotel can help arrange these for you when you’re ready!
Day 1: Welcome to Wine Country
9:00 AM –Meander Through Town
Once you arrive in Dundee, take a moment to breathe it all in. You’re surrounded by some of the best vineyards in the world—but there’s no rush. Start your trip with a stroll through downtown and pop into Red Hills Market for a bite. Their breakfast sandwich is practically famous, but don’t just take our word for it—ask your local vendors for their daily recommendations!
11:00 AM – A Sparkling Start at Argyle Winery
If you’re new to wine tasting, sparkling is a great way to begin. It’s fun, refreshing, and bright, and Argyle is the gold standard. Their sleek, modern tasting room offers approachable flights of méthode champenoise bubbles (aka, the fancy stuff, made the traditional French way), plus several still wine options for those who prefer less carbonated varietals.
First-timer tip: Don’t swirl sparkling wine—just sip and savor.
1:00 PM – Olive Oil Tasting at Red Ridge Farms
Take a scenic 10-minute drive to Red Ridge Farms, home to the only Olioteca (Olive Mill) in the PNW. That’s right, we make olive oil here!
The tasting room at Red Ridge Farms allows you to sample estate-milled oils for free. Peppery, buttery, grassy… you’ll be surprised by how nuanced olive oil can be. And their beautiful, serene plant nursery is the perfect place for a post-tasting wander.
Optional Add On: If you feel like an additional tasting, Durant Vineyards shares the property, so you can walk less than a minute and find yourself in your second tasting room of the day.
4:00 PM – Golden Hour at Furioso
Next, head to Furioso Vineyards. This architectural gem is a favorite for first-time visitors as it captures everything that makes Oregon wine country special: beautiful wines, a jaw-dropping view, and a laid-back elegance that’s pure Dundee.
Furioso’s tasting room, with its floor-to-ceiling glass walls, is perched above endless vineyard rows and looks west—making it a prime golden hour spot. And if you want our personal two cents: the estate-grown Pinot Noir and Friulano are both must-tries.
Additional note: Ask about Furioso’s estate-grown Italian varietals—they’re a fun curveball for adventurous sippers!
5:30 PM – Official Check In & Dinner at Trellis
It’s time to officially check in! Drop off your bags and grab your keys—but don’t settle in just yet, because there’s one more wine country stop today.
Dinner tonight is at one of our favorite spots: Trellis. Cozy yet elegant, Trellis offers a rotating menu of locally sourced dishes with a thoughtful Oregon wine list. You have the choice to sit inside, but whenever the weather allows, we recommend asking for a table outside on their heated patio—and don’t skip the Pinot Noir-braised short rib!
Note: Trellis is walking distance from the hotel if you prefer not to drive.
Day 2: Adventure, Pinot, and a Side of Whiskey
5:00 AM – Hot Air Balloon Ride or Morning Hike
If you’re an early bird—or just want to check something unforgettable off your bucket list—Vista Balloon Adventures launches just 10 minutes away in Newberg. Soar over vineyards and patchwork farmland as the sun rises. To call it “magical” would be an understatement.
Prefer to keep your feet on the ground? Head to Harvey Creek Trailhead or Champoeg State Heritage Area for a peaceful morning hike. Both offer easy-to-moderate trails, perfect for clearing your head (aka: making room for wine).
Note: Balloon rides are seasonal, so stick to the hike below if you’re visiting during our colder months. And if you’re hiking, feel free to hit that snooze button, as starting around 9:00 or 10:00 AM will still give you plenty of time for the rest of your activities.
12:00 PM – Iconic Tasting at Domaine Serene
No visit to Oregon wine country would be complete without a stop at Domaine Serene, one of the region’s most prestigious wineries. Known for world-class Pinot Noir and Chardonnay, this estate offers seated tastings with sweeping vineyard views, and a warm, knowledgeable staff.
This next part is important though… if you’re new to wine, let them know! This is a place where questions are welcome and every pour comes with a story.
Note: Domaine Serene offers small bites like charcuterie, sliders, artisan bread, and oysters—perfect for snacking as you taste.
1:30 PM – Additional Optional Food Stop
Before you head to your next tasting, we recommend an additional food stop here. This time, it’s the customer’s choice, but a few recommendations we have are Los Kopitos (the spicy carnitas gorditas are particularly scrumptious) or The Dundee Bistro (another famous nearby Oregon wine country staple).
2:30 PM – Whiskey Break at Ransom Spirits
It’s time to mix things up! Head to Ransom Spirits, conveniently located in Dundee as part of Duck Pond Cellars. Their tasting room features small-batch whiskey, gin, and grappa—all made with the same terroir focus as the local wines.
Fun fact: the experts here love nothing more than helping whiskey newbies find a favorite!
Evening – Wine & Food Experience
Tonight, we suggest opting for something interactive. Local wine and culinary businesses often host seasonal events—paella parties, chef-led pairings, even winemaker dinners.
If nothing’s on the calendar, try a wine blending session at Dobbes Family Estate or a vineyard hike at Knudsen Vineyards. However, if you choose the hike, swap this with Domaine Serene earlier in the day, as the hikes are often morning-only.
Note: Ask about upcoming events when you book your room at The Dundee. Our friendly staff is happy to help, but many of these experiences require advance reservations.
Day 3: Savor and Slow Down
11:00 AM – Get A Leisurely Start at Wooden Heart
Sleep in—you’ve earned it! Then make your way downstairs to Wooden Heart, conveniently located in the hotel. Everything on the menu is worth ordering, but we particularly recommend the eggs Benedict, breakfast pizza, or potato galette.
Note: Just make sure to save a little room, as your next stop includes another local delight!
12:30 PM – Cheese, Please
Cheese + wine = the original power couple. So of course we needed to include at least one cheese tasting on this itinerary.
It’s time to visit Briar Rose Creamery, where handmade goat cheeses are crafted with love (and serious flavor), and tasting is available onsite.
You can’t go wrong ordering anything, but our personal recommendation is to grab the fromage blanc and drizzle it with a little olive oil and pepper. Spread it on a baguette from Red Hills Market and—well, you’ll never go back to mass-produced grocery store cheese again.
2:00 PM – One Final Tasting at Branch Point or Sokol Blosser
Not quite ready to head home? Wrap up your trip with one final tasting. However, what you taste this time is up to you! Shall it be wine or whiskey?
- For Whiskey: Head to Branch Point Distillery in Dayton for Oregon-grown, grain-to-glass spirits—including their immensely popular rye whiskey.
- Wine: Visit Sokol Blosser, one of Oregon’s founding wineries, for a relaxing and scenic final flight.
Either Way, it’s time to toast to your trip and plan your next adventure to wine country!
A Few Final Tips for First-Time Tasters
- You don’t need to know a thing. Every winery on this list welcomes guests of all experience levels. Ask questions, be curious, and follow your taste buds.
- Reservations are highly encouraged. Especially on weekends—call ahead, book online, or ask The Dundee staff to assist.
- Pace yourself. Two to three tastings a day is more than enough to savor the experience.
- Food is your friend. It’s okay to take breaks and stop for food at any point of the itinerary!
Ready to book? The Dundee Hotel is proud to be your launching point for unforgettable wine country experiences. Book your stay today, and let us help you plan that perfect first sip