Holiday theater, warm mineral water and a few welcoming shops and tasting rooms, about an hour and a half up the road.
The morning starts the way most winter mornings do here: coffee at the round table by the stove, frost on the garden, and one of you checking the road report on a phone. The pass looks clear. By the time the sun is fully up over the valley, you're heading north on I-5, climbing over the Siskiyou Summit toward Oregon. A few hours later you're walking through downtown Ashland with a bag of something from a local shop, and by dark you're back in Scott Valley, boots off, telling the stove all about it.
Ashland is our favorite winter day out from the house. It's an artsy, welcoming town with real theater and a strong holiday season. Before you go, see what's on around Etna on our events calendar, then use this guide to plan the day.
Getting there: Siskiyou Summit, chains and daylight
Ashland is roughly 75 miles from Etna by way of Yreka and I-5, about an hour and a half in good weather. Check the drive in your maps app before you set out. The road north crosses the Siskiyou Summit on I-5, which can close in winter storms. That's the part to take seriously.
Check Caltrans QuickMap before you leave for chain controls, closures and road cameras, or call the Caltrans line at 1-800-427-7623. Check again before you head home.
Carry chains that fit and know which wheels drive your car. When chains are required, expect about a mile between the sign and the checkpoint, and drive 25 to 30 mph with them on.
Drive in daylight and stay together. Leave after breakfast and plan to be back over the summit before dark.
Pack the basics: a scraper, shovel, flashlight, water, food and blankets, with a full tank. Caltrans has more winter driving tips.
If a storm is forecast, pick another day. Ashland will still be there, and the stove is a fine consolation.
Holiday theater: Anne of Green Gables
Oregon Cabaret Theatre closes its 2026 season with Anne of Green Gables, a holiday musical running November 20 to December 31 at 241 Hargadine Street. It's dinner theater, so the show and the meal come together. Showtimes are on the box office page. For a day trip, look for an earlier performance that gets you home before dark, and book ahead in December.
A choir in Medford: December 18
The Southern Oregon Repertory Singers perform A Scattered Light in Winter on Friday, December 18, from 7:00 to 9:30 PM at the Holly Theatre in Medford. It's one of the group's most popular holiday programs, with Whitacre's "Stopping by Woods" and carols from around the world, and tickets run $13 to $62 (Jefferson Public Radio listing; group site at repsingers.org).
We'll be honest: it's an evening concert, so going means driving home over the summit after dark. We'd only plan it with a clear, dry forecast, with QuickMap checked before you leave the theater, and we'd skip it if the weather turns.
Festival of Light (confirm before you go)
Ashland's Festival of Light kicks off the holiday season downtown on the day after Thanksgiving every year, which would be Friday, November 27. The 2026 schedule hasn't been announced yet, so please confirm before you go. Last year it ran from 3 PM with performances on the Plaza, Santa's parade at 5 PM, and then the Grand Illumination of downtown (Ashland.news). The lights come on after dark, so if you go, it's another evening drive home. Plan it the same careful way.
The ice rink (confirm before you go)
The Ashland Rotary Centennial Ice Rink, near Lithia Park, was closed all of last season for a canopy retrofit. The city says it's on track to open in November, but there's no firm date yet, so confirm on the city's page before you plan around it. An afternoon skate and a walk through the park would make a good daylight half of the day.
Jackson Wellsprings (check hours and policy first)
Jackson Wellsprings, at 2253 Highway 99 North in Ashland (541-482-3776), is a naturally alkaline mineral spring with no added chemicals. It has a large pool around 80°F, a hot tub at 100°F or warmer, private tubs, a sauna and a steam room. A long soak on a cold day is hard to beat. Directories disagree about hours, prices and the evening policy, so check the current details on their website or by phone before you go.
Cafes, wine and shops
Ashland has a well-earned reputation as a welcoming, artsy town, and plenty of its local businesses are part of that. Travel Southern Oregon's LGBTQ+ travel guide is a good list of local favorites. A few from it that suit a winter day:
Sammich for a casual lunch stop between the theater and the shops.
Circadian Cellars for a wine tasting. Keep it to the passengers if you're driving the pass later.
Latitude Wine Tours if you'd rather someone else did the driving between wineries.
Winter hours change, so check ahead. Then spend an hour wandering the downtown shops for holiday gifts before you turn for home.
A simple Ashland day
Morning: check QuickMap, then leave after breakfast.
Late morning: a long soak at Jackson Wellsprings, once you've confirmed the hours.
Midday: lunch, then the downtown shops.
Afternoon: a skate if the rink is open, or an early show at the Cabaret.
Before dark: back over the summit to Etna, with QuickMap checked again.
Where you come home to
The best part of a day out is the drive back into Scott Valley as the light fades. The house is quiet and yours, the stove is a match away, and every bedroom has blackout curtains for a slow morning after. At founding rates for Sovereign Circle members, low season (November to February) is $555 a night, three nights from $1,090, and a week for $2,000, with cleaning and every fee included. The 14% county lodging tax is shown before you pay. For four adults, three nights is $1,242.60 all in, about $311 each. Joining the Circle is free through December 31, 2026.
Common questions
How far is Ashland from Etna? Roughly 75 miles by way of Yreka and I-5, about an hour and a half in good weather. Check the drive in your maps app before you go, and allow extra time in winter.
Is I-5 over the Siskiyou Summit open in winter? It can close in winter storms, and chains are sometimes required. Check Caltrans QuickMap before you leave and again before you head home.
Is Ashland a good day trip from Mount Shasta and Scott Valley in winter? Yes, with holiday theater, a mineral springs soak, downtown shopping and the ice rink once it opens. Plan the drive for daylight.
Is Jackson Wellsprings open in winter? It's listed as a year-round spring, but hours, prices and the evening policy vary between sources. Check jacksonwellsprings.com or call before you go.
Good to know
Anne of Green Gables runs November 20 to December 31. The Festival of Light and the ice rink opening are expected but not confirmed, so check both first.
Drive in daylight, stay together, carry chains and check QuickMap both ways.
Check-in at the house is 3 PM and checkout is 11 AM. No pets.
Our concierge can help you plan the day. Text 530 572 1122 or email Concierge@blossomsanctuary.com.
Pick a clear day, then check dates and price your stay. For more ideas close to home, see what's on around Etna on our events calendar and our guide to three days in Scott Valley.
