What to pack when traveling to a new place can be daunting, which is why I put together this brief list of important facts & useful tips for visiting Ashland, Oregon.

Ashland is located in Southern Oregon, just a few miles from the California boarder. It is almost equal distance between San Francisco and Portland on I5 therefore it’s the perfect stop. Surrounded by two great mountain ranges, the Cascade and Siskiyou, it’s gorgeous yet unpredictable when it comes to the weather. Often in the winter when I leave my home which is located 2 miles away from the Bayberry Inn, up on the mountain above the boulevard by Southern Oregon University, I am in the mist and fog until I get down to Main St where it’s a few degrees warmer and sunny.

While Ashland is pretty small with only 20,000 people, we do have access to many stores where you can always pick up anything you might have forgotten, like a toothbrush, but packing for the weather is always a good idea especially if you’re planning on visiting the Oregon Shakespeare Festival. Both the Green Show, which is wonderful, free and different every day and the Elizabethan Theatre at OSF are outside. While we are nothing like Portland, we do get some rain. Mostly though, it’s a few hours in a day before it clears up. We’re famous for growing Pear & Grapes which is why Harry & David is a few miles away and we’re surrounded by over 70 vineyards. So it can go from being super dry and hot in the summer and wet & wild in fall and winter.

Here’s some information I hope helps you prepare for your trip! Keep in mind if you’re coming to Ashland for the amazing hiking & mountain biking (Outdoor Magazine voted us best little town), you’ll want to consider what to pack a bit differently.

Weather Channel online is a great place to start when deciding what to pack for Ashland.

What to Pack
  • comfy walking shoes (you will do a lot of walking in Ashland & the Bayberry Inn is just a few blocks to downtown so most guests park their cars and don’t drive much if any during the rest of their stay in Ashland)
  • umbrella (small extendable is best)
  • rain coat (if visiting in summertime, lightweight and long is best)
  • hat (it’s a hot sunny walking town with beautiful parks to visit such as Lithia Park)
  • warm throw or blanket (if visiting in the Fall when the Elizabethan Theatre is still open)
  • warm coat in Spring, Fall & Winter
  • sun block

Extra Tips: If you’re coming in the Fall & seeing a play at the Elizabethan Theatre, make sure to book tickets under the awning in case it rains.

  • Bi-Mart 2280 Ashland Street
  • Ashland Drug 53 North 2nd Street
  • Rite Aid 2341 Ashland Street
  • Asante Ashland Community Hospital 280 Maple St. (541) 201-4000
  • Valley Immediate Care 1401 Siskiyou Blvd., Suite 1 (541) 488-6848
Gas Stations
  • Astro
  • 76
  • Shell
  • Texaco
  • Chevron

Gas StationTip: there are several Gas stations in and around Ashland. Avoid filling up at both entrances to Ashland off I5 because the prices are much higher than in town.

Electric Car Hookup Stations (Click Here)
Tire Shop
  • Les Schwab 2308 Ashland St.
Car Mechanic
  • Ashland Auto Repair  75 Lithia Way, Ashland (541)-552-9800

I hope I have included some helpful information for traveling to Ashland, Oregon. Feel free to call me at the Bayberry Inn for more information or if you have any further questions! We look forward to seeing you soon.


Beautiful view of rolling hills around Ashland, Oregon.