Best ski towns: Ashland, Oregon

A friendly community with a small-town yet academic atmosphere, Ashland, Oregon makes our list of Best Ski Towns despite the fact that it’s a full 20-minute commute from the slopes. What it lacks in proximity to powder it more than makes up for in charm, family-friendly shops and restaurants, and seasonal events, making it impossible to exclude. Located directly off I-5 in Southern Oregon and known for its vineyards, organic culinary scene, and Shakespearean festival (more on that below), Ashland is the most mild-weathered, cultured ski town we know.


Where to ski: I’m biased, as Mt. Ashland Ski Area is our home ski resort, but due to its small size and refreshing price point, it truly is a wonderful place for families. Mt. Ashland’s motto is, ‘It’s steeper here’, and they mean it! The runs are steep, but they’re not too long, allowing families to feel comfortable letting older kids and teens do some exploring. Mt. Ashland’s historic lodge is old school: the roaring fires and wood-cut benches are the real deal. (Sack lunches are welcomed, though the counter service restaurant serves a mean veggie burger, too.) You’ll find a ski and board rental shop and repair shop next to the lodge, reasonably priced (that seems to be a theme) lessons, and kids six and under ski or board for free.

Where to stay: Mt. Ashland doesn’t boast overnight accommodations, but thanks to Ashland’s world-famous Shakespearean festival, the town has no shortage of wonderful places to stay. If you plan to spend most of your time on the slopes, stay at the base of the Mt. Ashland access road at Callahan’s Mountain Lodge, but if you plan to spend any length of time exploring Ashland proper, I recommend staying in walking distance at boutique (and historically preserved) Ashland Springs Hotel or more economically at the Best Western Bard’s Inn, one of the nicest of its brand. Many B&B options also line the streets, and home rentals are usually available via HomeAway.

Where to eat: If you opt for a hotel room, no worries: given the culinary fame of this town, you won’t mind the lack of a kitchen! With kids, I recommend the filling (and innovative) breakfast options at either Dragonfly or Munchies. For an apres ski dinner, head to the cozy fireside dining room upstairs at Alex’s.

What to do when not on the slopes: Right in town, you’ll want to stop at the Ashland Centennial Ice Rink for a spin around this outdoor arena (across from gorgeous-in-all-seasons Lithia Park), before warming up at ScienceWorks Hands’ On Museum. You’ll also want to set aside time for some quaint shopping; even the kids will enjoy it, given the number of great toy and book stores. If your kids are old enough to appreciate great theater (and are able to stay awake after a day of skiing) evening tickets to a show at Ashland’s Oregon Shakespeare Festival (ongoing in their Globe and indoor theaters) are a must.

How to get here: From either CA or WA, take I-5 north or south. If flying, fly into Medford International Airport (MFR), located 15 miles north of Ashland.

Read more Best Ski Town picks!

About the author

Amy Whitley AUTHOR: Amy Whitley is the founding editor of Pit Stops for Kids and content editor of Trekaroo. She writes on staff monthly as a family travel expert at Go Green Travel Green and Practical Travel Gear, and contributes to Outdoors NW as an outdoor adventure traveler. Find Amy at Google.




  1. If you need a break from skiing the slopes, Ashland has many outstanding trails above the town for hiking, running or cycling. It’s a great combination being able to ski the mountain in the morning at 25°F and, within a short drive, be on the local trails at 45-65°F through most of the winter. Also, no trip (especially with kids) is complete without great pizza – Martolli’s in down town Ashland (38 East Main St.) is excellent. Happy skiing and enjoy beautiful Ashland.

  2. Danya Greene says:

    “Simply Sitters of Ashland operates with the utmost professionalism in matching the needs of clients with quality child care solutions. Freedom from fear ensures stress free time while away from your most precious asset. Be assured that Simply Sitters of Ashland consistently provides a safe, nurturing, and fun environment for your children while providing the parent peace of mind.” ~Robert L., Ashland, OR

    Our local team of highly qualified, trustworthy Sitters are on call and available to care for your child(ren) in the safety of your vacation home or hotel. We have personally interviewed and screened each Sitter to make sure each individual meets our high standards. Each Sitter is 19 years of age or older, First Aid and CPR Certified and background and referenced checked and is highly experienced. Contact us by email or phone at 541.261.2002. We are an Ashland Chamber of Commerce Member. Visit us on Facebook.

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