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604 Fair Oaks Ct, Ashland, OR 97520

The Best Of Ashland, Oregon Hiking Trails

Ashland, Oregon Hiking Trails – There’s a reason Ashland, Oregon has a reputation. For many, it’s the Hundred-Acre Wood they’ve always longed for. It is safe, friendly, surrounded by gorgeous vistas, and blessed with four equally potent seasons. 

Not least of its desirable features are the 47 miles of hiking trails in its greater boundaries. Whether you’re new to Ashland or simply looking for a local adventure, this blog post should get you on your way with two of the best Ashland, Oregon hiking trails.

Two Of The Best Ashland, Oregon Hiking Trails

Ashland’s Fairy Ponds

Nestled at the foot of the National Forest, the Ashland Fairy Ponds are a portal to your favorite childhood fantasy, and they’re practically at your doorstep. 

Ashland Fairy Pond hiking Trails

Many are content exploring the utopic reaches of Lithia Park, and we don’t blame them, but for a little extra privacy, simply follow Winburn Way uphill to Granite Street, take a left, and continue to Ashland Reservoir. There’s a dirt road leading left–walk past it, through the parking area until you reach a wooden corral fence and the beginning of the trail. 

Now enjoy the shade of the canopy, the sun-dappled meadows and burbling riffles and pools that give this section of Ashland Creek its name. Wade to your favorite boulder, pull out a book (might I suggest some Henry Thoreau?), and linger as long as you like. 

Ashland Oregon Hiking Trails Fairy Ponds

Soda Mountain Wilderness: Pilot Rock

This one is for the thrill-seekers among you. So named by nineteenth-century pioneers who relied on it for a landmark, Pilot Rock is an iconic feature of Ashland’s landscape. The trail is a three-mile out-and-back that’s as challenging as it is rewarding, as anyone who’s seen this 360-degree view of the Rogue and Shasta Valleys will tell you. 

Drive south on I-5, exiting at Mt. Ashland. Head toward the Mt. Ashland Road turnoff but continue straight, under the freeway. At the second left, you’ll see a sign for Cascade/Siskiyou Pilot Rock. Be advised, this is a bumpy dirt road. From Ashland to the parking lot, it’s only about a 30-minute drive. 

The trail is short but steep. In today’s parlance, we might say it goes “zero-to-a-hundred”. The middle section coincides with the Pacific Crest Trail, where you can continue for a mellower outing. But should you stick to Pilot Rock trail, you’ll be led to a sheer switchback that requires some scrambling but no equipment. We only recommend this part for the sure–and perhaps cloven-footed. Please use caution!

Once you’ve reached the top (congratulations!), you’ll be met by an eye-watering panorama of Mt. Ashland, Mt. Shasta, Mt. McLoughlin, the Rogue Valley, and the Shasta Valley. It’s one of Ashland’s best hiking trails–surely the most epic. Celebratory sandwiches are mandatory. 

Ready To Explore One Of These Ashland, Oregon Hiking Trails?

These jewels of natural splendor represent both ends of the spectrum of Ashland’s tremendous network of trails. Whether you’re a visitor, a local, or a recent addition to the community, we hope you get a chance to enjoy them as we have. Now, lace up those boots!

For more epic Ashland, Oregon hiking trails, check out AllTrails.com.

Looking For More Ways To Explore Ashland, Oregon?

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