From Forest Trails to Festival Days: A Southern Oregon Itinerary for Families

Many years ago, after an unexpected stint back east, we moved to Oregon to be closer to home and family, and Ashland — Southern Oregon’s cultural hub — was the first place we took a road trip with our baby daughter. While the area’s small-town charm, family-friendly vibe, and self-guided farm and wine trail first piqued our interest, over the years we’ve come back many times, most recently with our now-older kids who can finally appreciate the renowned Shakespeare festival that draws visitors from near and far every year. 

Why visit Southern Oregon? 

Many flock to the area for the Oregon Shakespeare Festival (OSF) in Ashland, now in its 90th year, but that’s just the beginning. Just north of the California border, Southern Oregon’s climate is relatively mild with low rainfall, compared to other parts of Oregon. Its mountains, fertile valleys and high desert areas support a thriving outdoors culture and robust food and wine scene. Whether you seek outdoor adventure, theater and arts, food and wine trails, or want to visit the mighty Rogue River or even Crater Lake, the region is well worth the drive south. 

Where to stay 

Many make charming Ashland — known for its arts and culture, walkability, numerous shops and restaurants, and beautiful Lithia Park — their home base when visiting Southern Oregon. While there are many Ashland hotels to choose from, we stayed at the economical Best Western Windsor Inn, about 10 minutes by car from downtown, with a pool and hot breakfast. The Lithia Springs Resort, a short six-minute drive from the city center, offers 38 accommodations and has been significantly remodeled since our earlier stay. It now offers a dog-friendly “Family Suite” with two bedrooms, two bathrooms, a kitchenette, and a seasonal outdoor saline pool and jacuzzi to enjoy. 

By choosing to stay in Medford, the largest town in the Rogue Valley and just a short 23-minute drive from Ashland, you’ll likely find broader and more economical lodging choices. You’ll also be closer to Jacksonville, a historic gold rush town that is considered one of America’s best small towns, the Applegate Valley wine region, and Crater Lake National Park, which is just an easy day trip away. 

If a peaceful mountain escape is more your speed, adventurous families might enjoy staying in the Cascade-Siskiyou National Monument. This area is a biodiversity hot spot that protects habitats for countless birds, mammals, reptiles and amphibians, many of which are rare or endangered. There’s not a lot of infrastructure here, making it a tranquil escape for nature-lovers. We recently stayed at the Green Springs Inn, a lodge and cabin retreat, featuring affordable high-country lodge rooms, nine deluxe cabins with jacuzzi tubs, dog-friendly options, a peaceful setting and miles of nearby trails. Hyatt Lake Campground, with 44 campsites (reserve ahead), is another option for those looking to camp or on a tighter budget. 

No matter which home base you choose, all the itinerary ideas described below are just a short drive away! 

Things to do with kids in Ashland 

Introduce them to Shakespeare or a contemporary play at OSF. 

The Oregon Shakespeare Festival (OSF), one of the oldest and largest professional nonprofit theaters in the country, has drawn a crowd to Ashland since its start in the 1930s. Children over the age of 6 are welcome to attend performances, and we’ve loved taking our kids to a few special performances during the past two seasons. They occasionally offer discounts for school-aged children or student groups, so make sure to investigate specials as you’re planning your visit. 

For parents of younger kids, check out the OSF’s free summer and fall Green Shows on the Courtyard Stage Tuesday through Saturday, June to September, all ages welcome. 

Location: 15 S. Pioneer St., Ashland 

Experience life like a royal at Lovejoy’s British High Tea. 

Tucked into a whimsically decorated space near Lithia Park is Lovejoy’s Tea Room, where guests can enjoy afternoon tea, the lighter tea fare menu and more. My teenage daughter and I have now experienced two full “Queen’s Tea” services, and it has become a special tradition for us. Tea service includes a choice of teas (including herbal, green or seasonal iced teas), fresh fruit, salad, tea sandwiches, warm scones, crumpets with lemon curd and assorted sweets. The “Wee Tea,” for children younger than 10, features child-friendly options. Families can also build their own à la carte tea service for a less formal experience. 

Location: 96 N. Main St., Suite 201, Ashland 

Burn off your sugar rush at beautiful Lithia Park. 

Locals refer to Lithia Park not only as the centerpiece of Ashland but also as a “mini Golden Gate Park.” John McLaren, the designer of Golden Gate Park, also played a role in the development of this much smaller-scale (it’s only 93 acres), but equally beautiful, urban park that is conveniently located south of downtown, along a picturesque creek that winds up a canyon. Other highlights include picnic areas, the duck pond, babbling brook, a great playground for kids of all ages, and a Japanese Garden. Lithia Park is also known as a great place to see fall foliage, with its diversity of tree species, including oaks and Japanese maples; we’ve also enjoyed cherry blossoms here in the spring. It is truly an urban oasis for all seasons. 

Location: 59 Winburn Way, Ashland

Immerse yourself in ScienceWorks interactive exhibits and hands-on fun. 

ScienceWorks Hands-On Museum, located in Ashland and serving Southern Oregon and Northern California, is an interactive museum for learners of all ages to immerse themselves in interactive STEAM exhibits, workshops and programs. Founded in 2002 in response to a crisis in public science education, it is designed “for curious minds of all ages.” The current featured exhibit, “Paleoart Through Time,” examines the way that artists’ depictions of dinosaurs have changed over the last 100 years, in both pop art and scientific illustration, and is running through September. 

Cost: Adults, $12.50; kids, $10.50; kids younger than 2 are free. SNAP members receive up to four tickets for $3 each. They also participate in the ASTC Travel Passport Program. 
Location: 1500 E. Main St., Ashland 

Things to do with kids in (and near) Medford 

Hop aboard a train at Medford Railroad Park.

If your kids are as crazy about Thomas the Train as mine were, you’re going to love the volunteer-run Medford Railroad Park, regardless of your age. The 49-acre park is open every second and fourth Sunday from April to October, 11 a.m. to 3 p.m. and is free to the public (donations are welcome). Highlights include real train cars and a caboose, a scaled train to ride, indoor and outdoor model trains with all the scenery, and a Thomas the Tank Engine train for the younger kids. We found friendly and passionate volunteers stationed in the train cars to answer all of our questions, and fun, free activities for the little kids. They also have nice picnic areas and allow well-mannered leashed dogs. 

Location: 799 Berrydale Rd., Medford 

Relax and enjoy live music, food and wine at Dunbar Farms and Winery. 

Nestled within the Medford city limits near the country club is family- and pet-friendly Dunbar Farms, a 112-year-old fourth-generation century farm. The tasting room is open Thursday–Saturday, 11:30 a.m.–8 p.m., and from 11:30 a.m.–6 p.m. on Sundays. It offers “more than charcuterie” lunch, dinner, wine and other beverages. Families will find free live music three nights per week, and friendly horses to pet when you visit. The farm, while not certified, follows organic practices and produces produce, grass hay and wine. 

Location: 2881 Hillcrest Rd., Medford 

Hike to incredible views of the Rogue Valley. 

If you’re an outdoors family, you’re in luck, because there are several great family-friendly view hikes to choose from in the Rogue Valley. Roxy Ann Peak and Prescott Park, just a 22-minute drive from downtown Medford, feature a network of trails, including the 3.5-mile 700-elevation peak with views that extend to Mt. Shasta and picnic areas. The Table Rocks, 23 minutes north of town, is another popular area for hiking. Upper Table Rock (2.5 miles and 720 feet) is most popular during wildflower season (March–May) but is open year-round, and boasts incredible views of the entire valley from the top of a plateau. Lower Table Rock (3.5 miles and 780 feet) has interpretive panels and views of the Rogue River. No dogs allowed. 

Visit biodynamic Troon Vineyard & Farm in the Applegate Valley. 

The fertile Applegate Valley, a picturesque rural area in Southern Oregon, is home to 18 wineries. We’ve enjoyed several trips to Troon Vineyard & Farm, the world’s only Demeter Biodynamic and Regenerative Organic Gold Certified winery and farm with beautiful views of the Siskiyous, and it happens to be very kid- and dog-friendly too. From June 22–Sept. 28, it also offers a farmers market with produce, artisans, live music and lunches with ingredients from the Biodynamic farm. Open daily from 11 a.m.–5 p.m. 

Location: 1475 Kubli Rd., Grants Pass (Located about 40 minutes west of Medford and under one hour west of Ashland.)