A Rogue Valley wine weekend itinerary is all about options: big views, small-lot weirdos, classic estates, and a few pleasantly scrappy upstarts. The good news? Many of the most interesting Rogue Valley wineries sit within an easy drive of each other, so you can build a compact, high‑impact route without spending your day in the car.

Below is a practical guide to nearby wineries worth visiting during a Rogue Valley wine weekend itinerary, plus how to structure your days so you hit more great pours and fewer tourist traps.

---

How to structure your Rogue Valley wine weekend itinerary

Before listing specific nearby wineries, it helps to frame your weekend:

• Home base: Most visitors stay in Ashland, Medford, or Jacksonville. All three are close to clusters of tasting rooms.
• Pacing: Aim for 3–4 wineries per day. That’s enough to explore without palate fatigue.
• Mix it up: Combine:
  • One or two established estate wineries
  • One small, experimental producer
  • One scenic, linger-all-afternoon stop
• Reservations: Increasingly necessary on weekends—especially for seated tastings, groups, or vineyard tours.

With that in mind, here are nearby Rogue Valley wineries to plug into your weekend.

---

Wineries near Ashland worth adding to your route

Ashland is a natural hub: theater town, good food, and quick access to multiple Rogue Valley wineries. If your Rogue Valley wine weekend itinerary starts or ends here, these are strong nearby stops.

Irvine & Roberts Vineyards (Ashland)

• Why go: High-elevation site, serious focus on Pinot Noir and Chardonnay, and some of the best vineyard views near Ashland.
• What to expect: Modern tasting room, seated tastings, and a more “Burgundy‑leaning” style than many Rogue Valley reds.
• Best for: Starting your day—clean, precise wines set your palate up nicely.

Weisinger Family Winery (Ashland)

• Why go: One of the area’s early players, with a welcoming, low‑pretense vibe.
• What to expect: A broad mix—Viognier, Tempranillo, Syrah, Bordeaux blends—and a relaxed tasting room just outside town.
• Best for: A drop‑in stop when you’re staying in Ashland and want good wine without a production.

Belle Fiore Winery (Ashland)

• Why go: The “wow” factor. Think hilltop estate, grounds made for photos, and a wide variety of wines.
• What to expect: Larger, more ornate setting than many Rogue Valley wineries. A long list including Cabernet Franc, Merlot, Syrah, and blends.
• Best for: A late‑afternoon visit where non‑wine friends can be impressed by the setting while you dig into the wine list.

Grizzly Peak Winery (near Ashland)

• Why go: Under‑the‑radar, laid‑back tasting room with live music on some evenings.
• What to expect: Views of the surrounding hills, approachable reds and whites, and a local, community feel.
• Best for: A casual stop if you like your wine with a side of music and minimal fuss.

Sample Ashland‑centric day:

• Late morning: Irvine & Roberts for focused Pinot/Chardonnay.
• Mid‑day: Weisinger for a broader spectrum of Rogue Valley varieties.
• Late afternoon: Belle Fiore or Grizzly Peak for views and lingering.

---

Wineries near Medford to anchor your Rogue Valley weekend

Medford sits in the middle of several Rogue Valley wine trails and is practical if you want easy access in every direction.

RoxyAnn Winery (Medford)

• Why go: Historic Hillcrest Orchard turned winery; a staple for many Rogue Valley wine weekend itineraries.
• What to expect: Cabernet Sauvignon, Claret‑style blends, Syrah, and accessible whites in a rustic‑chic tasting barn.
• Best for: A reliable first or last stop—solid wines, easy to reach, plenty of outdoor space.

2Hawk Vineyard & Winery (South Medford)

• Why go: Attractive estate feel and a broad portfolio with an Old World slant.
• What to expect: Tempranillo, Malbec, Viognier, Grenache, and more, often with food pairings or small bites available.
• Best for: A leisurely seated tasting where you can try multiple Rogue Valley expressions in one place.

DANCIN Vineyards (north of Medford, near Jacksonville)

• Why go: Precision‑driven Pinot Noir and Chardonnay, with wood‑fired pizzas and gardens that practically demand a long stay.
• What to expect: Terrace seating, flights that highlight different clones and vineyard blocks, and a more culinary‑driven experience than many.
• Best for: A long lunch stop in your Rogue Valley wine weekend itinerary.

Kriselle Cellars (White City, short drive from Medford)

• Why go: Focused on big, structured reds that show how warm parts of the Rogue Valley can go toe‑to‑toe with more famous regions.
• What to expect: Cabernet‑driven blends, Tempranillo, Sangiovese, and an airy tasting room overlooking vineyards.
• Best for: Red‑wine lovers who like their wines bold and age‑worthy.

Sample Medford‑centric day:

• Late morning: RoxyAnn for a historic, approachable intro.
• Lunch/early afternoon: 2Hawk or DANCIN for wine plus food.
• Late afternoon: Kriselle for bigger reds and a sunset view.

---

Wineries near Jacksonville for a more historic, small‑town vibe

Jacksonville is a compact, walkable town with 19th‑century charm—and it’s ringed by Rogue Valley wineries within a short drive.

DANCIN Vineyards (Jacksonville side)

• Why go: Serves as a bridge between Medford and Jacksonville, making it easy to pair wine tasting with dinner in town.
• What to expect: Pinot, Chardonnay, pizza, and a setting that feels designed for long, chatty tables.
• Best for: A central anchor to build the rest of your Jacksonville wine route around.

Quady North (Jacksonville tasting room)

• Why go: Focused on Rhone‑style wines and Cabernet Franc, with an emphasis on vineyard‑specific bottlings.
• What to expect: A tasting experience that leans more into the “wine geek” side: site distinctions, blends, and unusual varieties.
• Best for: Drinkers who want to understand Rogue Valley’s micro‑climates through the glass.

South Stage Cellars (downtown Jacksonville)

• Why go: Downtown tasting room pouring wines from multiple vineyard sites, including some of the oldest in the region.
• What to expect: Flights that highlight the diversity of Rogue Valley fruit: Viognier, Malbec, Tempranillo, Syrah, and more.
• Best for: A tasting you can walk to before or after exploring historic Jacksonville.

Sample Jacksonville‑centric day:

• Late morning: Quady North for a deep dive into specific vineyard bottlings.
• Afternoon: DANCIN for a more leisurely, food‑focused break.
• Late afternoon/early evening: South Stage Cellars, followed by dinner in downtown Jacksonville.

---

Scenic and off‑the‑beaten‑path Rogue Valley wineries

If your Rogue Valley wine weekend itinerary can handle a bit of extra driving, these slightly farther‑flung wineries are worth adding.

Wooldridge Creek Winery (Applegate Valley)

• Why go: Winery + creamery + charcuterie—essentially a DIY picnic in wine country.
• What to expect: Grenache, Tempranillo, Cabernet Franc, and more; plus artisan cheeses and meats made on site.
• Best for: A long, lazy afternoon where you’re as excited about the food board as the flight.

Troon Vineyard (Applegate Valley)

• Why go: Biodynamic, soil‑driven, with a strong focus on Mediterranean and Rhone varieties.
• What to expect: Vermentino, Tannat, Syrah, Mourvèdre, and blends; a thoughtful tasting format and strong educational bent.
• Best for: Wine travelers who love organic/biodynamic farming and are open to less conventional varieties.

Schmidt Family Vineyards (Applegate Valley)

• Why go: Elaborate gardens and manicured grounds, plus a broad lineup of wines.
• What to expect: Pizza, outdoor seating, and relaxed tastings—family‑friendly and group‑friendly.
• Best for: Mixed groups where some people want to stretch out on the lawn while others work through a flight.

Applegate‑focused day (add‑on to Rogue Valley weekend):

• Late morning: Troon for biodynamic, experimental wines.
• Lunch/afternoon: Wooldridge Creek with cheese/charcuterie.
• Late afternoon: Schmidt Family for gardens and a final, easygoing flight.

---

Tips to get more from your Rogue Valley wine weekend itinerary

To make all these nearby wineries work together smoothly, a little planning beats winging it.

1. Cluster wineries by geography

Instead of zigzagging between Ashland, Medford, and Jacksonville, cluster your visits:

• Day 1: Ashland + south Rogue Valley
• Day 2: Medford + Jacksonville
• Optional Day 3: Applegate Valley extension

This minimizes drive time and maximizes tasting time.

2. Mix styles and sizes

Balance your schedule so you don’t visit four near‑identical tasting rooms in a row:

• Pair a large estate (Belle Fiore, RoxyAnn, Schmidt) with a smaller, more focused producer (Quady North, Troon, Irvine & Roberts).
• Alternate between white‑leaning stops and red‑leaning stops so your palate doesn’t burn out.

3. Book ahead—especially for groups

Most Rogue Valley wineries are happy to accommodate walk‑ins during slower times, but for a prime weekend itinerary:

• Make reservations for at least one or two anchor tastings per day.
• Mention if you’re serious tasters (interested in vineyard/production details) so they can seat you with staff who love those questions.

4. Think beyond the tasting flight

Rogue Valley wineries often offer:

• Library tastings of older vintages
• Food pairings or chef‑driven snacks
• Vineyard tours or barrel tastings by appointment

Adding even one of these to your weekend can turn a standard stop into a standout memory.

5. Have a logistics plan

• Hydration & snacks: Water between wineries and neutral snacks (nuts, crackers) will keep you sharp.
• Designated driver: Many of the roads between wineries are scenic, narrow, and curvy. Rotate drivers or hire a local tour/transport service if you plan a full day of tasting.
• Bottle strategy: Decide what you want to bring home—daily drinkers, cellar‑worthy bottles, or gifts—and take notes so you remember why you liked each wine.

---

Putting it all together

A Rogue Valley wine weekend itinerary works best when it blends nearby wineries with different personalities: a high‑elevation Pinot specialist here, a biodynamic experimenter there, and a couple of big‑view estates in between. Start by choosing your home base (Ashland, Medford, or Jacksonville), then plug in 3–4 wineries per day from the lists above, clustering by location and style.

You’ll end up with a Rogue Valley weekend that feels less like a box‑checking tour and more like a curated conversation with the region—one glass at a time.