Sample Itineraries

some ideas for a great stay

Enjoy Ashland with these itinerary ideas...

Outdoor Adventure

(request or view our Ashland Map Guide for trails and hikes)

  • Cool off white water rafting or kayaking on the Rogue or Upper Klamath rivers
  • Cycle along the hills of Ashland, Bear Creek Greenway or for adventure riders, the Cascade Siskiyou Scenic Bikeway, a 55-mile loop climbing 5000’
  • Visit the Mountain Lakes to go fishing, paddling or swimming
  • Enjoy the trail systems of the Ashland Watershed, Lithia Park and Oredson-Todd Woods while trail running, hiking, birding or mountain biking
  • Witness the seasonal wildflowers on Grizzly Peak and Mt. Ashland
  • Hike and picnic at Grouse Gap Shelter along the Pacific Crest Trail
  • Take a leap and discover a zipline adventure

Award-winning culinary scene

  • Taste and tour the wineries of Ashland, Bear Creek, Applegate or Upper Rogue
  • Tour a brewery and sample at the two amazing microbreweries
  • Get fresh produce at the Growers and Crafters market Tuesdays and Saturdays
  • Enjoy a cocktail made by one of Ashland’s talented mixologists
  • Experience amazing dishes at one of Ashland’s 100 restaurants
  • Take a cooking class from a local chef or culinary educator

Unmatched Culture

  • Shop art galleries and shops in the Historical Downtown or Railroad Districts
  • Take a self-guided tour: Public Art or Trees of the Year (
  • Tour SOU’s campus, home to the Schneider Museum of Art, Oregon Center for the Arts, Chamber Music Concerts and Rogue Valley Symphony
  • Take a Backstage tour at the Oregon Shakespeare Festival
  • Check out the local, live music scene with talented, local musicians

Ashland’s Historic Railroad District

  • Experience authentic Ashland like a local, stroll the historic neighborhoods
  • Rent a bike and hop onto the designated bike path to explore Ashland by bike
  • Plan your day’s adventure over coffee, pastry, a cocktail or delicious meal at one of the Railroad district’s cafes or eateries
  • Explore shops and art galleries in between yoga classes at one of the many studios
  • Bring your kids, dogs and a picnic to the Ashland Railroad District Park and check out Ashland’s last Golden Spike

Mid-week in Ashland

  • Go golfing at Oak Knoll Golf Course or play pickleball
  • See art being created by local artists at one of Ashland’s fine artisan locations
  • Relax with a soak, massage, manicure or pedicure at one of the spas
  • Book your next group visit, tour or conference with Travel Ashland and Neuman Hotel Group
  • Take a day trip to Crater Lake National Park

For More Itinerary Ideas check out the new 2023-2024 Visitor Guide

Featured Things for Planning