Ashland, Oregon, is a small town in Southern Oregon with a big reputation.

Thanks to the Oregon Shakespeare Festival, Southern Oregon University, and the surrounding beauty of the Siskiyou Mountains Ashland is a popular destination.

Here are a handful of links to help you plan your trip.

One – Weekend in Ashland

Our Weekend in Ashland post will help you plan your perfect weekend getaway.

Choose your own adventure with our suggestions for making the most of each day.

Two – Two podcast episodes

Amateur Traveler’s – Ashland Oregon’s Shakespeare Festival Episode 37

All Around the West – Ashland, Oregon: Podcast 26

Three – Self-guided tours

Travel Ashland Self-Guided Tours

Great story maps – interactive, 3-D, searchable, often with photos.

Current maps include:

• Ashland tree of the year
• Ashland public art
• Cemeteries
• Lithia Park tour
• Lithia Park historic map tour
• Little free libraries

Four – A Little Tour of Ashland, Oregon

Oregon Family Adventures – A Little Tour of Ashland, Oregon | Home of the Shakespeare Festival

This video is from 2018, but it’s still a good representation of Ashland and its charms.

Five – Applegate wine trail

Southern Oregon is wine country. Find everything you need to book a guided tour or find wineries to visit on your own.

Applegate Valley website.

We would love to hear about your trip to Ashland. You can message us on Instagram, Facebook, or Twitter. Let us know if you found one of these links helpful.