Ashland may be famous for Shakespeare and alpine trails, but tuck just ten minutes south of town and you’ll find the real headliner: Belle Fiore Winery & Vineyard. Picture a French‑style château perched above rolling vines, its terraces draped in string lights and its kitchen turning out estate‑grown pairings—from truffle‑dusted fries to Sicilian lamb meatballs—designed to elevate every pour. Because Belle Fiore offers both immersive reserve tastings and a full slate of chef‑driven dishes, you can plan an entire getaway around a single address without sacrificing variety or town‑center convenience.
This itinerary shows you how to do exactly that: anchor each day’s highlights—parks, theater, artisan markets—around Belle Fiore’s tours, flights, and seasonal plates, so your Ashland weekend flows as smoothly as a glass of their estate Cabernet Franc at sunset. Ready to sip, stroll, and savor? Let’s map out the perfect wine‑centric escape.
Day 1 (Fri): Arrive & Ease Into Ashland
Time | Experience | Insider Tip |
3 p.m | Check‑in downtown—Ashland Springs Hotel or an Airbnb loft. | Staying in town means a quick, $15 rideshare to Belle Fiore. |
4 p.m | Lithia Park stroll along Ashland Creek. | Grab a mineral‑water sip at the plaza fountain. |
6 p.m | Dinner at Alchemy Restaurant & Bar (killer local wine list). | Ask the sommelier to open a Belle Fiore bottle for a preview. |
8 p.m | Oregon Shakespeare Festival curtain or free Green Show. The 2025 season runs March 7 – Oct 26. Oregon Shakespeare Festival |
Day 2 (Sat): Full Belle Fiore Immersion
Morning
- Breakfast downtown (e.g., Morning Glory), then a ten‑minute scenic drive to 100 Belle Fiore Ln.
Mid‑Day: Taste & Dine on Estate Favorites
Slot | What to Do |
12 p.m. | Château Tour & Reserve Tasting (Sun slots, too; book on Tock). |
1:30 p.m. | Shared‑plate lunch in the Pavilion:
• Cheese & Charcuterie Board—cured meats, local cheeses, house bread Belle Fiore Winery & VineyardBelle Fiore Winery & Vineyard • Seasonal Bruschetta on fresh‑baked sourdough Belle Fiore Winery & Vineyard • Sicilian Lamb Meatballs with arrabiata & hazelnut gremolata Belle Fiore Winery & Vineyard • Truffle Fries topped with aged parmesan Belle Fiore Winery & VineyardBelle Fiore Winery & Vineyard |
3 p.m. | Chef‑selected wine‑and‑food pairing flight—curated bites match each pour in the Lower Tasting Room. Belle Fiore Winery & Vineyard |
4 p.m. | Garden stroll & photo op; shop art‑label bottles to ship home. |
6 p.m. | Upper Wine Bar dinner—mix & match heartier plates Petite Beef short rib with Pinot Noir demi. Belle Fiore Winery & Vineyard |
Sunset | Toast golden hour on the Mountainview Terrace; music most weekends (see events calendar). |
Day 3 (Sun): Encore Tasting & Ashland Highlights
Time | Plan |
10 a.m. | Second‑look Pavilion tasting—try the Summer Salad (beets, berries, goat cheese, Muscat vinaigrette) as a light brunch bite. Belle Fiore Winery & Vineyard |
12 p.m. | Optional Château Tour |
3 p.m. | Lithia Artisans Market for handmade gifts. |
5 p.m. | Picnic on OSF Green Show lawn with a pre‑packed Belle Fiore charcuterie box before your final performance. |
Practical Planning Tips
- Reserve early. Estate tours, terrace tables, and OSF seats sell out fast.
- Skip driving. Local shuttles or rideshares run Belle Fiore round‑trips for under $25.
- Layer up. Even July nights dip into the 50s °F—bring a wrap for terrace tastings.
- Ship wine. Belle Fiore can send bottles to 40 + states—keep your suitcase light.
- Check the events calendar for live‑music evenings and chef pop‑ups.
Book Your Belle Fiore Experience First
With estate‑sourced plates like Sicilian Lamb Meatballs and that crowd‑favorite Cheese & Charcuterie Board anchoring your day, everything else—parks, theatre, downtown shopping—falls perfectly into place. Reserve your Château Tour now and let Belle Fiore set the rhythm for an unforgettable Ashland wine weekend. Cheers!