Outdoor adventures with Bayberry Inn & Oregon Wellness Retreat.

Offering private or group guided hikes. Has 2 bikes available for your use, while your with us!

Ashland is a Hiking & Biking Mecca for outdoor junkies.

The jewel of Southern Oregon, Ashland is uniquely situated where the Cascades & Siskiyou Mountain ranges meet. It is not only beautiful, but also the perfect place for outdoor adventure such as skiing, trail running, hiking and/or mountain biking. Ashland offers everything from light one hour hikes to extremely steep climbs where you’re sure to get your adrenaline pumping. Described as ‘cheap, deep & steep,’ Mt. Ashland is a great ski mountain and offers a pretty incredible varied terrain but in the summertime, it’s a wonderland of hiking & biking trails. You can access the trails across the street from the Bayberry Inn Bed and Breakfast at the top of the hill within minutes. Please ask us for trail maps & in-side info on all the nearby hikes and bike rides.

Hiking Trails

Grizzly Peak
High above Ashland in the Siskiyou- Cascade National Monument is the most spectacular hike called Grizzly Peak. Located 30 minute up above Ashland at 5,922-foot is the trail head which takes you through forests that open out onto meadows and at the top you get to the most spectacular views of Mt. Ashland, Mt. Shasta & Mt. McLoughlin. Luckily you climb most of the elevation in your car so the actual hike from the trailhead is 2.5 miles and not difficult. It’s perfect for families and for a perfect day, take a picnic and your camera and enjoy the day.

Pilot Rock
Located outside of Ashland on the way to Mt. Ashland you’ll find a stunning 2.8 mile hike called Pilot Rock. Beautiful wild flowers line this gorgeous hike and the bottom part is easy and accessible for anyone. The closer you get to the top, however, it becomes more difficult and technical. The trail is primarily used for hiking and is best used from May until October. Dogs are also able to use this trail but not at the top where it becomes shale & dangerous.

White Rabbit Trail
Gorgeous easy to difficult trail. My favorite place to start this hike is from the top of Park Street on the South Side of town, as it offers spectacular views,(click for map)

Lithia Park
A gorgeous place to take an easy stroll, Lithia Park is the jewel of our town. Accessed from downtown Ashland, about 5 blocks from the Bayberry Bed and Breakfast you can take an easy stroll or a rigorous hike up into the mountains. (click for map)

Hald Strawberry Park
Accessed from downtown but to avoid a steep climb to get to this park, drive up to the top of Grandview (from Church street).

Mike Uhtof Trail
Entrance can be accessed from the top of Park Street.

Oredson Todd Woods
Part of the White Rabbit & Mike Uhtof trails which can be accessed from the top of Park St.

Biking Trails

Bear Creek Greenway
A lovely place for long distance road bikes. You can access this trail less than a mile from the Bayberry Inn Bed and Breakfast on Oak Street. Don’t forget to take your tire fixing kit as there are not a lot of places to get help along the way.

Ashland Biking Trails
There are many rides from Ashland which can take you 3 to 30 miles and more.

Please be cautious when hiking and biking our trails for they can be quite extreme in spots and you will be in and out of cell phone reception. It’s best to take your phone, let someone you leave behind know where you’re planning on hiking and take plenty of water and snacks. Give someone your itinerary and agree on an estimated finish time at which time you will call them to let them know you have returned safely.