Road Trip: A Week in Southern Oregon with Kids - 510 Families
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Road Trip: A Week in Southern Oregon with Kids

After browsing Amy Whitley’s impressive website, Pit Stops for Kids, I invited her to contribute a vacation recommendation for Bay Area families. I’m pleased to publish her guest post here.

Looking for an easy getaway this summer? Southern Oregon provides Bay Area families with lots to do in a beautiful, natural setting…and guess what? Contrary to popular Oregon myth, it hardly ever rains! Located just over the California border an easy six hour drive up I-5, the Cascade and Rogue Valley areas of Southern Oregon are home to Harry and David, ample wineries, the world famous Shakespeare Festival, mountain lakes and streams, and Crater Lake National Park. Here’s how we suggest you spend a week with your family in Southern Oregon.

oregon road trip tips

Day 1 (Monday): Driving to Ashland, Oregon from the Bay Area

Your first stop over the California-Oregon border is the thespian town of Ashland. If you have school-aged or teen children, you’ll definitely want to take in a play at the Oregon Shakespearean Festival in the outdoor Globe theater, but if your kids are very young, there’s still lots to do. Visit downtown’s beautiful Lithia Park, where you can walk trails, wade in Lithia Creek, and play on the large playground. Ashland’s downtown is filled with fun stores to poke into, from toy stores and bookstores to eclectic shops featuring costumes, jewelry, and just about everything else under the sun.


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Ashland is filled with family-friendly (yet still adult-pleasing) dining.

We recommend Dragonfly, for its outdoor patio and Latin-Asian fusion cuisine even toddlers will love, or Sesame, located right on the plaza and offering asian specialties, fried rice, and stir-fry. When not exploring the town, hike nearby trails at Mount Ashland Ski Area or try out the award-winning Scienceworks museum.

Things for families are pretty spread out in Southern Oregon (it’s a big area!) so make Ashland your home base for the next week (with plenty of optional overnights elsewhere). Our favorite family-friendly hotels in Ashland include the Best Western Windsor Inn and the Lithia Springs Hotel.

Day 2 (Tuesday): Jacksonville and the Applegate Valley

If you have desire to sample Southern Oregon’s many wine labels, plan an afternoon in the Applegate Valley, fifteen miles outside of nearby Jacksonville, Oregon. The many wineries dotting this beautiful valley are fabulous…and most are kid-friendly. End your afternoon swimming at Applegate Lake, or touring the historic pioneer town of Jacksonville. Kids will love the Pioneer Museum (as well as more toy shops and candy stores), and parents will enjoy the unique shopping and historical points of interest.

Day 3 (Wednesday): Lake of the Woods and Oregon Cascades

On your third day in Southern Oregon, beat the heat (yes, it really will be warm!) and drive 45 minutes from Ashland into the mountains to cool off in Lake of the Woods. Tucked away in the Cascade Mountains, Lake of the Woods offers swimming, boating, canoe and kayak rentals, fishing, and hiking. Grab a day picnic spot right on the lake shore, or play to spend the night in one of the rustic (but family-friendly) lakeside cabins. Just be sure to reserve one early in the season!

Adventurous families will want to expand their lake day with a hike in the Sky Lakes Wilderness (trailhead located less than 1 mile from Lake of the Woods). This network of trails takes hikers to one of half a dozen mountain lakes. The first is only a few miles from the trailhead, making it a possible option even for young hikers. Take a dip in the cool lake waters before returning to Lake of the Woods for a lodge dinner.


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Day 4 (Thursday): Union Creek and Crater Lake National Park:

A day trip to Crater Lake National Park is a must. The two-hour drive from Ashland or the Rogue Valley up the Rogue Umpqua National Scenic Byway can be broken up with a stop at Beckie’s, an Oregon institution in Union Creek, Oregon. Eat a lunch of burgers and their famous milkshakes, then hike to the Rogue River Natural Bridge where it’s fun to see the Rogue River disappear through lava tubes.

Crater Lake with kids

Once you’ve wound your way (beware of car sickness!) up to Crater Lake, take in the breathtaking views at the visitor’s center, where you’ll learn how this impossibly blue lake was formed. Take the rim trail, or drive to the Watchman Observation Station, where families can take the short (but steep) hike to the old fire tower. Not only do kids love the climb and the novelty of playing on a real fire tower, but the views are fabulous (as are the photo opportunities!).

Day 5 (Friday): Oregon Caves and Redwoods

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Back in the Rogue Valley, drive up I-5 to Grants Pass, Oregon, where you’ll leave the freeway behind for winding Highway 199 and nearby Cave Junction, Oregon. Visit Oregon Caves National Monument, but be advised that kids must be at least 42″ to take the tour. Younger kids will have plenty to do hiking the nearby trails or playing around the historic lodge, but plan to leave an adult with them. Continue on Highway 199 to get a glimpse of the redwoods at Jedediah Smith State Park, or go another 30 minutes to the coast at Brookings, Oregon (our favorite beach is Harris Beach State Park).

On your way back to the Rogue Valley, stop at the amazing Out ‘n About Treesort in Cave Junction to zip line, horseback ride, or just soak in their natural pool. Better yet, make a reservation to stay a night in your very own tree house! Bring your own food to BBQ or cook in the communal kitchen, or eat out at a local favorite: Wild River Pizza.

Out n About Treesort

Day 6 (Saturday): Return to Ashland or Whitewater Raft

Return to Ashland for a final day of biking along the Plaza and park, taking in a show, or shopping. If you have older children (and are adventurous), take a whitewater rafting trip down the Rogue River. Noah’s Rafting leaves right from the Plaza for a full day or half day on the Rogue.

Note: If you visit Southern Oregon in winter, you can still do all of the above activities: you’ll just save money on your play tickets, ice skate at Lithia Park instead of creek wade, snowshoe at Lake of the Woods, and snowmobile around Crater Lake! Oh, and the skiing is affordable and fun at Mount Ashland! In other words, you can’t lose!

Amy Whitley is a freelance travel writer and editor of Pit Stops for Kids, a travel resource for any parent who’s heard ‘Are we there yet?’. Amy makes her home in Southern Oregon with her husband and three school-aged children.

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3 thoughts on “Road Trip: A Week in Southern Oregon with Kids”

  1. We stayed in Out ‘n About Treesort a few years ago. It was so much fun. It’s a rustic B&B in the trees. The zip line course was so much fun.

  2. Lake of the Woods is where my family used to spend many a week during summers 45 yrs ago! Don’t even need to go anywhere else. My best memory is catching polywogs, which probably isn’t permitted anymore. Great place!

  3. Pingback: Treehouse Camping Oregon | Our Meeting Rooms

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