Welcome to Southern Oregon’s Rogue Valley, where Ashland’s theater lights meet forested canyons and river spray. This 7-day trip balances culture and nature: Oregon Shakespeare Festival by night, whitewater and wineries by day, and historic main streets in between. You’ll split time between Ashland and nearby Grants Pass for easy access to the Rogue River.

Ashland grew from a mill town into a nationally known arts destination led by the Oregon Shakespeare Festival (OSF). Stroll Lithia Park’s 100 acres of Japanese gardens, duck ponds, and creekside trails, then sip award-winning pinot noir at hillside vineyards like Irvine & Roberts. Grants Pass, an hour northwest, is the Rogue’s launchpad—famous for canyon walls, swimming holes, and bald eagles at dusk.

Practical notes: Fly into Medford (MFR), 25 minutes from Ashland. Spring through early fall brings theater, rafting, and vineyard patios; winters add skiing at Mt. Ashland. Reserve OSF tickets in advance, and confirm river trip water levels in shoulder seasons. This itinerary features local restaurants, coffee roasters, and 1–4 handpicked Viator activities to lock in your adventures.

Ashland

Ashland is equal parts stage and trail. By day, wander boutiques and bookshops along Main Street; by night, settle into a velvet seat beneath the Elizabethan Theatre’s timbered arches. The town’s heart is Lithia Park, designed by a disciple of John McLaren (of Golden Gate Park fame): a ramble of stone bridges, towering firs, and the music of Ashland Creek.

Eat and drink like a local: begin at Noble Coffee Roasting (single-origin pour-overs and flaky kouign-amann) or Case Coffee Roasters (award-winning espresso). For dinner, Alchemy Restaurant & Bar at the Winchester Inn plates seasonal Oregon fare with a serious wine list; Cucina Biazzi serves Northern Italian classics in a cozy cottage garden. Pints? Head to Caldera Brewery Restaurant for an epic tap list and mountain views.

• Where to stay: Search stays on VRBO Ashland or compare hotels on Hotels.com Ashland.
• How to get here: Fly into Medford (MFR). Check fares on Trip.com flights or Kiwi.com. Typical nonstop hops from SFO, SEA, or LAX are 1.5–2 hours, often $120–$350 roundtrip.

Day 1: Arrive, Ashland Old Town, and Lithia Park

Morning: Travel day.

Afternoon: Arrive at MFR, pick up a rental car, and settle into your Ashland stay. Stretch your legs with an easy loop in Lithia Park: start at the Japanese garden, follow the creek to the duck ponds, and pause by the sycamores for photos.

Evening: Dinner at Alchemy Restaurant & Bar—think Oregon trout with fennel and citrus or a wine-braised short rib—then a nightcap at the Winchester Inn bar. If timing aligns, catch OSF’s free outdoor Green Show (summer) for a lively sampler before your first theater night tomorrow.

Day 2: Downtown Ashland, Self-Guided Audio Tour, and OSF

Morning: Coffee at Noble Coffee Roasting; try the Ethiopia natural as a pour-over with a cardamom bun. Explore indie shops: Bloomsbury Books (literary treasures), Paddington Station (Northwest gifts), and Varsity Theatre’s classic marquee for a photo.

Afternoon: Dive into Ashland’s story with this highly rated self-guided walk:

The Cultural Heart of Ashland: A Self-Guided Audio Tour
Creativity meets mountain scenery on a narrated stroll through Ashland’s most storied blocks.

Lunch at Brickroom Gathering House (Korean fried chicken sandwich or a kale Caesar with crispy quinoa) overlooking the plaza.

Evening: See an Oregon Shakespeare Festival performance—classics, new plays, or musicals depending on the season (Feb–Oct). Pre-show dinner at Cucina Biazzi; their pappardelle with wild mushrooms and the tiramisu are local favorites.

Day 3: Rogue River Whitewater + Rogue Valley Wine

Morning: Grab a latte at Case Coffee Roasters on Siskiyou Blvd, then head north for a half-day splash that’s ideal for first-timers and families:

Rogue Valley Rapid Run
Closest whitewater to Ashland with a fun progression of rapids and swimming spots.

Expect 3–4 hours door-to-door; most trips depart from Phoenix/Talent area.

Afternoon: Celebrate with vineyard views. Start at Irvine & Roberts (pinot noir, chardonnay, airy patio) and Weisinger Family Winery (syrah, tempranillo, valley vistas). Share a charcuterie board for a light late lunch.

Evening: Casual dinner at Smithfields Pub & Pies—steak & ale pie with a side of mushy peas—or head to Caldera Brewery Restaurant for a Thai red curry pizza and a flight of IPAs. Stroll along Ashland Creek under café lights before bed.

Grants Pass

Grants Pass sits at a bend in the Rogue, where boat ramps and outfitters are as common as coffee stands. The downtown’s vintage neon declares its motto—“It’s the Climate”—and the surrounding hills are laced with trails to river overlooks and secret swimming holes.

Food and drink skew Northwest comfort: Taprock Northwest Grill for riverfront burgers and cedar-plank salmon; The Twisted Cork for Oregon wines by the glass; Rogue Roasters for small-batch coffee; and the original Dutch Bros drive‑thru for a local rite of passage.

• Where to stay: Browse VRBO Grants Pass or compare hotels on Hotels.com Grants Pass.
• Getting there from Ashland: Drive ~1 hour via I‑5 N (about 48 miles). Aim for a morning departure to check in and hit the river by late afternoon.

Day 4: Transfer to Grants Pass + Golden Hour on the Rogue

Morning: Breakfast at Brothers’ Restaurant in Ashland (lingonberry pancakes or the chorizo scramble), then drive to Grants Pass. Check in and wander the murals and antique shops downtown.

Afternoon: Early dinner at The Twisted Cork—order the Dungeness crab cakes and an Oregon pinot flight.

Evening: Float into sunset with this tranquil, wildlife-forward drift:

Rogue River Golden Hour Evening Float Trip
As twilight falls, the canyon glows and herons hunt—the river at its most peaceful.

Day 5: Hellgate Canyon Whitewater + Riverfront Eats

Morning: Fuel up at Rogue Roasters (honey lavender latte and a warm croissant), then tackle the Rogue’s scenic narrows:

Rogue River Hellgate Canyon AM Half-Day Trip
Granite walls, fun Class II–III wave trains, and swim breaks in sheltered eddies.

Afternoon: Lunch at Taprock Northwest Grill by the pedestrian bridge—try the elk burger or cedar-plank steelhead. Walk Riverside Park; watch for osprey nests along the river.

Evening: Dinner at River’s Edge Restaurant (reservations recommended for patio tables). If you’re a beer fan, swing by Weekend Beer Company for a crisp pilsner and food-truck tacos.

Day 6: Caves and Vines—Oregon Caves or Applegate Valley

Morning: Choose your adventure. Option A: Drive ~1.5 hours to Oregon Caves National Monument for a ranger-led tour through marble caverns (bring a jacket; it’s ~44°F inside; check seasonal tour times). Option B: Wine day in the Applegate Valley—visit Troon Vineyard (biodynamic blends), DANCIN Vineyards (pinot noir and wood-fired pizza), and a riverside picnic.

Afternoon: Return via Grants Pass’s historic district for browsing and espresso at the original Dutch Bros (where the chain began). Pick up Rogue Creamery blue cheese in nearby Central Point if you’re passing through.

Evening: Casual comfort at Ma Mosa’s (scratch-made seasonal plates) or a cozy steak at Blondie’s Bistro. Turn in early for departure day.

Day 7: Back to Ashland/Medford and Depart

Morning: Drive back toward Medford. Brunch at Buttercloud Bakery & Café (biscuits with sausage gravy, lemon curd scone, and a macchiato). If time allows, stop at RoxyAnn Winery’s Hillcrest Orchard for a final bottle to take home.

Afternoon: Fly out of MFR. Check last-minute fares or schedule changes on Trip.com or Kiwi.com. Safe travels!

Optional or Family-Friendly Swaps

• Rogue River Family Float & Discovery Park-Rafting and Kayaking – mellow water, great for kids: Book here

  

• Ashland Puzzling Adventure – a playful two-hour app-guided game in town: Book here

  

In one week you’ll taste Southern Oregon’s best: Ashland’s theater and tree-lined paths, river days that glow at golden hour, and wines poured where the foothills meet the sky. It’s a trip that dances between curtain calls and canyon walls—one you’ll remember with every future sip of pinot and the sound of a rushing river.