Ashland Oregon Itinerary Ideas

Active Travel Ideas from Ashland Oregon

Ashland Oregon is our home base and the jumping off point for our Upper Klamath Whitewater Safari Trips. Ashland has become a place where culture, nature, and outdoor adventure come together. It is home to the Oregon Shakespeare Festival, tons of wineries, unique hotels, amazing restaurants, hiking, biking, trail running, and an amazing walkable downtown. And it is a jumping off point for some of the world’s most spectacular rivers. Here are just a few ideas for things to mix with an Upper Klamath Trip – it is easy to put together a great 3 to 6-day itinerary.

Ashland Outdoor Adventure:

– World Class trail running and hiking right from downtown (and the Rogue Valley Runners Store ) and the Pacific Crest Trail and the Siskiyous are a short drive away. Add in a friendly and laid back running community that includes some of the world’s best trail runners past and present.  Here is a detailed trail map >>

– Hike the Pacific Crest Trail  from one of a dozen entry points near Ashland.

– Mt Ashland itself – rising 5000+ feet above Ashland it provides for amazing hiking (including the Pacific Crest Trail), trail running, an biking (and in the winter, one of the steepest little ski areas anywhere).

– World-Class Mountain biking including 5000’ trail and road descents from Mt Ashland to downtown. And tons of other trails, once again, starting right from downtown (you can literally coast off of the mountain into downtown and a brewery!). Call our friend Bill and Ashland Mountain Adventures.

– Road bike the Cascade Siskiyou Scenic Bikeway – Flywheel Bicycles is a great resource.

– Ashland is also a great jumping off point for other Southern Oregon Adventures: Take a day or two to explore Crater Lake National Park, Jeb Smith Redwoods State Park and the Southern Oregon/Nor Cal Coast, or climb the 14,000’ glacier capped Mt Shasta with Shasta Mountain Guides.


Ashland Food, Wine, and Cultural Events:

– Ashland’s walk-able downtown is home to a ton of great restaurants, cafes, shops, and Lithia Park.

– Tour one of 150 wineries (Ashland was named one of 10 Best Wine Travel Destinations of 2016 by Wine Enthusiast).

– Enjoy fresh produce at the bustling farmer’s markets offered nearly year-round.

– Drink organic, artisanal, direct-trade coffee from one of several award-winning local coffee roasters.

– Sip spirits and drink beer at one of a growing number of local distilleries and breweries.

– Catch an outdoor concert and walk through the historic town of Jacksonville at the Britt Music Festival.

– And of course check out one of the plays (Shakespeare and modern performances) at the world-famous Oregon Shakespeare Festival.


Ashland is an amazing little town, a place we feel lucky to call home, and a great place to visit in the summer. There are so many great options! If you have any questions about coming to Ashland don’t hesitate to call or email – we can help you with all the trip planning.

Check out our Getting Here Page for Driving and Flight Info >>