Three Days in Ashland Itinerary

Top Ashland Attractions Include:

Top Breakfast Spots: Breadboard & Morning Glory

Relaxing Daytime Activities:

  1. Enjoy a play or show at the Oregon Shakespeare Festival, Oregon Cabaret Theater & Camelot Theater company.
  2. Take a leisurely walk through Lithia park, enjoy the new Japanese gardens.
  3. Wine taste at the Ashland Wineries; Belle Fiore Winery, Irvine & Roberts, Weisinger, Grizzly Peak, Eliana wines & Long Walk Vineyard.
  4. Taste along the Bear Creek Wine Trail.
  5. Shop around in the downtown Ashland Plaza

Evening activities:

  1. Dinner and nightly live music at Belle Fiore Winery
  2. Excursion to Britt Music Festival for live music under the stars in Jacksonville, OR
  3. Other top dinner recommendations: Alchemy, Peerless, Hearsay & Larks

Special Adventure Excursions:

  1. Chateau, garden, vineyard wine tour at Belle Fiore Winery
  2. Hiking on the Pacific Crest Trail near Ashland Pilot Rock, the “Alice in Wonderland” Trails or Greenspring’s Loop Trail.
  3. Skiing at Mount Ashland (Seasonal)
  4. Mountain Biking from Mount Ashland at Rabbit Ears drop- off (downhill biking) or the central Ashland bike path
  5. River Rafting the Rogue River; Shady Cove or Galice (seasonal)
  6. Wine Tasting Excursion to Applegate Valley, OR (Troon Vineyards, Schmidt Family Vineyards, Red Lilly, etc.)

Where to Stay:

  1. Ashland Springs Hotel
  2. Ashland Hills Hotel
  3. Plaza Inn
  4. Oak Hill Bed & Breakfast
  5. Bayberry Inn & Retreat
  6. Other Ashland Lodging

Day One

  • Visit Historic and beautiful Lithia park, This remarkable 93 acre park was designed over one hundred years ago by John McLaren (also designer of San Francisco’s Golden Gate Park) following the style of Frederick Law Olmsted. The nearly two-mile-long park features huge hundred-year-old trees and some fifteen bridges crossing historic Lithia creek.  Enjoy the new Japanese gardens opened in 2023.  Free to the public, no pets allowed.
  • Enjoy an afternoon wine tasting experience at Belle Fiore Winery just five to ten minutes from downtown Ashland. Belle Fiore offers splendid inside and outside wine tasting area, and offers all-day and evening dining out on the Grotto, Terrace and Plaza area in the midst of 30-acres vineyards, with rolling Tuscan-like hills and mountain scenery in the distance.
  • Enjoy a tasty dinner at AlchemyPeerlessHearsayLarks or another Ashland favorite eatery.
  • Complete your evening with an amazing live theatre experience under the stars in the outdoor Elizabethan Theatre or the indoors Bowmer Theater of the world-famous Ashland Oregon Shakespeare Festival.

Day Two

  • Drive for a one-to-three hour hike along the magnificent Pacific Crest Trail near Ashland Pilot Rock which is accessible from I-5 Mount Ashland Exit 6 just ten minutes south of Ashland. Trailhead parking is on the old Highway 99, or with a seasonal parking pass on the Pilot Rock trailhead parking area.  Twenty-mile vistas look south and west towards the Marble Mountains of Northern California.  As you hike pick out local landmark peaks including Mount Ashland and Mount McLaughlin in Oregon, and John Muir’s favorite, the heroic Mount Shasta in California.
  • Have breakfast or brunch at celebrated local dining spots, such as Breadboard, or Morning Glory.
  • See a matinee Play at Oregon Shakespeare Festival.
  • Or plan an excursion to hear live concerts on the outdoor grass amphitheater of the Britt Music Festival in the historic Victorian gold mining town of Jacksonville Oregon (a thirty-minute drive from Ashland).
  • Enjoy live music, and profound wine paired cuisine with an outdoor or indoor dinner at Belle Fiore Winery.
  • Grab a night cap at Oberon’s, The Black Sheep, Louie’s or other historic bars and venues in the Ashland Plaza downtown. What a fine way to end another fun-filled day in Ashland.

Day Three

  • If it’s a Sunday, sleep in. Or visit the local churches in Ashland which all welcome visitors.
  • Play a morning round of pickleball at Ashland’s highly popular Lithia park, Pickleball courts, with eight dedicated courts. Come early, and be ready to share the courts, as this booming sport is a favorite with Ashland residents.
  • Embark on a Wine tasting excursion: Visit Irvine & RobertsWeisingerGrizzly PeakEliana wines & Long Walk Vineyard all located in the outskirts around Ashland.  Or take a fabulous one to four hour drive out to the hidden gem of the Applegate Valley, OR just past Jacksonville to visit Troon VineyardsSchmidt Family Vineyards, Red Lilly. and other renown Applegate wineries.
  • You still have a chance to take in more culture: See a fun popular play or musical at the  Oregon Cabaret Theater or the Camelot Theater company.
  • Revisit your favorite places around Ashland! Visitors come back here again and again, as Ashland is truly a town for all seasons.

Exploring Ashland, Oregon




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