The Road to Ashland

Winter fun awaits you in this Southern Oregon mountain town, nestled right near the California border. Even in wintery driving conditions, you can travel safely if you follow a few key road-safety rules — check our Arriving Safely section at the end of the article for details. Without any stops (or inclement weather), you’ll get there in under five hours, but in classic road-trip fashion, we recommend breaking up the journey with a few easy pit stops — and we’ve got just the spots to recommend. 

Play Along the Way

1.   Gilbert House Children’s Museum
Learning through creative play is what it’s all about at this charming children’s museum named after Salem native A.C. Gilbert — scholar, Olympic gold medalist, entrepreneur, and inventor of the Erector toy construction sets. Best for kids 2-10. 116 Marion St. NE, Salem. Tuesday-Sunday, 10 am-5 pm. $8 general admission; free for kids under 1. Pro tip: Portland Children’s Museum members get in free! 

2.   The Oregon Garden
Need some fresh air? Stroll through the Children’s Garden on the 80-acre property that makes up the Oregon Garden. You’ll find a Swiss Family Robinson-style treehouse, a Hobbit house/tunnel, animal-shaped topiaries, and a dinosaur bones dig area, plus a working replica of the train that once ran through Silverton and the Willamette Valley. 879 W. Main Street, Silverton. Open daily, 10 am-4 pm. $8 for adults; $5 for kids 12-17; $2 for kids 5-11; free for kids under 4. Pro tip: November 29 to January 5, a portion of the gardens transforms into Christmas in the Gardens, a European-style nighttime Christmas market. 

3.   Historic Albany Carousel & Museum
See (and ride!) the carousel that a whole community built. It took more than 200 volunteers 10 years and 160,000-plus hours to lovingly restore and rebuild this historic 1909 carousel. The care and craftsmanship of each of the 52 hand-carved animals will leave you spellbound. 503 First Ave. West, Albany. Open Wednesday-Monday, 10 am-5 pm. Rides start at 11 am with a $2 token. Museum admission free.

4 .  Cascades Raptor Center
Visit one of the largest collections of native raptor species in the Pacific Northwest, where kids can view over 50 different birds of prey, including eagles, hawks, owls and vultures in large outdoor aviaries. You can also learn about the work being done at the onsite wildlife hospital. 32275 Fox Hollow Rd., Eugene. Open Tuesday-Sunday, 10 am-4 pm. Admission is $9 for adults; $6 for kids 2-12; free for kids under 2. 

5.   Wildlife Safari
Observe wildlife from the comfort of your car at this 600-acre drive-through animal park, which resembles the African plains and is also home to the country’s most successful cheetah-breeding program. 1790 Safari Rd., Winston. Open daily 10 am-4 pm. Admission is $21.95 for ages 13 and up; $15.95 for ages 3-12; free for kids under 2. (Additional animal-enrichment encounters start at $20.) No pets allowed; onsite kennels available.

Where to Stay

Drop your bags at the Ashland Hills Hotel & Suites, a fully remodeled family-friendly midcentury modern hotel just a short drive from downtown Ashland. The hotel will be fully decked out for the holidays and in January will offer a Kid’s Package that includes a winter-themed welcome bag with activity book, stickers, and other fun surprises, plus complimentary hot chocolate from Luna Cafe, the hotel’s all-day eatery and mercantile. Hotel amenities include: deluxe continental breakfast, laundry access, rollaway beds, portable cribs, complimentary board games, family movie rentals, and a photo booth. New this year: an on-site spa. (Because massages and road trips go together so well.) Pro tip: Be sure to snap a pic of your littles in the lobby’s groovy “Ball Chair.” Room rates begin at $89 plus tax. 

Where to Play Downtown 

Downtown Ashland will be illuminated this holiday season with more than a million lights during the Festival of Light Celebration, beginning November 29. Make a reservation to decorate gingerbread cookies and have Brunch with Santa on December 15 at Larks Home Kitchen Cuisine at the historic Ashland Springs Hotel. While you’re there, explore the lobby’s cabinets of curiosities — each is filled with rare objects from around the world.

Your kids will love searching for 30 tiny gnome doors hidden throughout the downtown area. Get a map from Tree House Books and find your first door just outside the bookstore entrance. Some miniature doors open to reveal a tiny treasure inside. Pack along some of your own trinkets and play gnome for the next child to discover. And Tree House Books is a great place to pick up last-minute gifts and stocking stuffers. In December, their shop window display will feature a “Gnome for the Holidays” diorama, with a very detailed gnome home complete with bedrooms, kitchen, and a magical crystal garden. Pro tip: The city of Ashland is a plastic-bag-free zone, so pack your own reusable shopping bags or pay a small fee for paper bags in stores.

The entrance to Lithia Park, the 93-acre crown jewel of Ashland, is located just around the corner from the bookstore. Before heading inside, sample the famous (and famously stinky) Lithia mineral water from the bubbling fountain. Pro tip: Have a camera ready to capture your kids’ best “Yuck!” faces. Inside the park, just across from the year-round playground, you’ll find the seasonal Ashland Rotary Centennial Ice Rink, which operates from mid-November through February. The rink is covered, but it’s open air, so come dressed for the weather. On-site ice skate rentals are available, from toddler size 9 up to men’s size 15.

Fans of the Oregon Museum of Science and Industry will really enjoy ScienceWorks Hands-On Museum. (Pro tip: OMSI members get in free!) Kids will love the numerous interactive hands-on exhibits. Don’t miss the Bubble Room, where visitors can stand inside a giant soap bubble!

Where to Eat

Morning Glory Breakfast, Lunch & Espresso  (1149 Siskiyou Blvd.) A local favorite where breakfast is the star. Substitutions are politely declined — you’ve been warned! 

Sammich  (424 Bridge St.). Before Portland fell in love with Sammich Portland and the Pastrami Zombie food truck, there was Sammich in Ashland. Best-in-class sandwiches by Ashland’s unofficial mayor chef/owner Melissa McMillan.

Flip  (92 N. Main St.) Artisan fast food with grass-fed beef, housemade organic brioche buns, fresh-cut fries, and all-natural sodas and shakes.

Hither Coffee & Goods  (376 E. Main St.) A thoughtfully curated cafe with a small but well-executed menu of hot selections, wine and flowers for sale — and the best chocolate chip cookies in Ashland.

Ashland Food Co-Op  (237 N. 1st St.) Ashland’s only certified organic retailer features daily hot bar specials, made-to-order sandwiches, tacos and burritos, smoothies, and food to go. Check their calendar for events, including a free gingerbread-cookie-decorating party on December 7 from 11 am-1 pm.

Happy Bowl Restaurant  (1401 Siskiyou Blvd.) This no-frills spots (a favorite among local chefs) is the place to go for Vietnamese pho noodle soup and spring rolls at a bargain price. 

Standing Stone Brewing  (101 Oak St.) A full-service brew pub with an expansive kids’ menu featuring all the greatest hits, plus a kid-approved snack tray. Kids’ beverage options include everything from organic cider (chilled or steamed) to housemade sodas and draft root beer. 

Zoey’s Cafe & All-Natural Ice Cream  (199 E. Main St.) Choose from 40 handmade flavors at this downtown scoop shop. If you’re hungry, grab a homemade calzone or wrap.

Fun Facts, Southern Oregon Edition

On weekends between mid-December and early January, you can adventure around Crater Lake — the deepest lake in North America! — on snowshoes. Call 541-594-3100 to sign up for a ranger-led snow hike. For kids 8 and up; no experience necessary. $15 per vehicle; includes snowshoes.

Founded in 1935, Ashland’s Oregon Shakespeare Festival is one of the oldest theater companies in North America, attracting visitors from all over the world to its March-October calendar of performances.

The best cheese in the world comes from Southern Oregon! Rogue River Blue by Rogue Creamery in Central Point was crowned The Best Cheese in the World at the World Cheese Awards in 2019. (Rogue River Blue is the only American-made cheese ever to receive this honor.) 

For most of its history, the Ashland Springs Hotel in downtown Ashland was the tallest building between Portland and San Francisco. This year marks its 95th anniversary. 

Beyond Ashland

From farm stays to winter wonderlands, holiday options abound for families visiting Southern Oregon — and many of our favorites are within 30 minutes of Ashland proper! 

Bet the Farm

If your kids like animals, visit Willow-Witt Ranch, an Oregon Tilth Certified Organic Ranch and farm stay. The 445-acre property is open to visitors throughout the year by reservation. (Just call ahead to let them know you’re coming and to ensure the roads are clear.) Tours are self-guided and no-charge. Since the weather can be cooler at this higher elevation, bring extra layers and wear waterproof boots if you’re worried about snow or mud.

Christmas Classics

Step back in time to historic Jacksonville, Oregon, and experience a true Victorian-era Christmas. You’ll find the town decorated in greenery, with white lights to evoke a bygone era. Enjoy strolling carollers dressed in Victorian garb, complimentary hot cider, and $1 rides on the Holly Jolly Trolley, which makes a quick loop around town. Make time to tour the Beekman House, the historic home of Jacksonville’s wealthiest and most prominent pioneer family, and see how the rich and famous celebrated Christmas in 1873. Weekend tours are $5 at the door and offered every 15 minutes from 11 am-2:45 pm every weekend from November 30 to December 20. Be sure to visit Scheffel Toys & More, an independent toy store with perhaps the largest Playmobil selection in Oregon. 

Snow Fun

Mt. Ashland Ski Area is tiny compared with other Oregon ski resorts, but that’s what makes it perfect for young families on a ski day — experienced or not. Kids under 6 and seniors always ski free, and an all-day pass on the beginner run is just $10 for everyone else. Mt. Ashland offers a range of super-affordable ski and snowboard rental packages as well as free door-to-door shuttle service from the Ashland Hills Hotel and Suites. If sledding sounds better, check out the Grouse Gap Sno-Park beyond the back parking lot of Mt. Ashland Ski Area or Table Mountain Snow Park, which now has a BYOW (bring your own wood) warming hut with wood stove. Pro tip: Neither has easy bathroom access, and carrying tire chains is recommended when driving at this elevation, so be prepared. 

Arriving safely

Winter driving in Oregon can be intimidating — prepare for the unexpected by packing along essential safety items and making a plan of action just in case you do get stuck. Below, our tips for helping you get safely on your way.

Know Before You Go Before you leave your house, always check the weather report and make sure driving conditions are safe. Within Oregon, call 5-1-1 for updated road conditions, or visit tripcheck.com for up-to-the-minute updates, including weather alerts, road closures and detours.

Stock Your Car’s Emergency Kit No matter the season, ODOT recommends keeping your car fully stocked with essential safety items. The basics include: a car-escape tool and a pocket knife (stored within reach of the driver’s seat); a first-aid kit with kid-appropriate medications; drinking water; high-energy, shelf-stable snacks; a headlamp with extra batteries; and basic road safety items like flares, jumper cables and triangle reflectors. A paper map of Oregon is also good to have on hand. In the winter, pack extra emergency blankets or sleeping bags (one for each family member!); extra cold-weather waterproof gear; a small shovel; an ice scraper with snow brush; cat litter or sand for traction; and tire chains and a tow strap. The Oregon Winter Driving Guide has full list of recommended items. Pro tip: always keep phones plugged into a USB charger when driving to avoid a low battery during an emergency.

You’re Stuck! Now What? Let’s say you’ve used your snow shovel to move the snow away from your wheels and sprinkled the cat litter to try to gain some traction, and you’re still stuck. Don’t panic! First, call or radio for help, and if you can’t get a cell signal, trying texting. While you wait, make sure your car is as visible as possible by doing the following: Turn on your hazard lights, put out triangle reflectors, place some brightly colored cloth on your antennae, and light a road flare. Move all your emergency supplies into the cab of the car, and bundle up as you wait. Conserve gas by only turning the engine on every now and then to keep yourself and your water from freezing. If the sun goes down, keep a light on in the car to make it easier to spot in the dark. If snow accumulates on the car, brush it off using the snow shovel, and brush the car as needed to keep it visible. Conserve food and water, but stay hydrated while you wait. Unless you can clearly see help in the immediate distance, do not attempt to walk for help. Stay put, and stay safe. 

Judiaann Woo is a food and travel consultant based in Portland. When she’s not helping brands better connect with their audience, she’s out seeking adventures with her two kids, dog, cat and her photographer husband. Follow her travels on Instagram at @judiaann.