Head South for the Winter to this Oregon Town

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Ashland packs a cultural punch throughout the year, including the winter months, making this town well worth the 4.5-hour drive from Portland.

Courtesy of Mt. Ashland Ski Area

Family Activities

Courtesy of Merrills on the Move and Travel Ashland

Ashland’s Festival of Light kicks off in November and lasts through the end of the year. The celebration starts with a tree lighting and parade the Friday after Thanksgiving, then fills the calendar with holiday-themed performing arts, including carolers and pop-up concerts downtown. Enjoy the roughly million lights strung throughout this Southern Oregon town and join the Chabad Jewish Center of Southern Oregon’s public menorah lighting during Hanukkah. Or meet Santa during one of his many public appearances and grab a ticket to A Gospel Christmas produced by the Rogue Valley Symphony.   

To take advantage of chilly days, skate your heart out at the Rotary Centennial Ice Rink in Lithia Park or strap on your skis, snowboard or snowshoes at the Mt. Ashland Ski Area. Kids 6 and under get free lift tickets! For those of you who are more indoor cats, explore interactive science exhibits at the ScienceWorks Hands-On Museum. Pro tip: The museum is free to OMSI members — just show your membership card — and starts at $10.50 without. Or go all-out with the sprinkles at the Ashland Food Co-op’s annual Cookie Party (December 14, free with food bank donation).

Family Dining

Courtesy of Caldera Brewing Company

Fuel a day of fun at Morning Glory, where you’ll order homey favorites like sourdough pancakes, house-smoked salmon scrambles and crepes. Enjoy Saturday morning live tunes alongside breakfast like challah french toast and pastries at La Baguette Music Cafe. Just don’t blame us if your kids sing 99 Bottles of (Root) Beer on the Wall for days after eating personal pizzas, pretzel bites and fish tacos at Caldera Brewing, with its display of countless bottles above the fabulously purple dining area.

Where to Stay

Courtesy of The Palm Motel & Cottages

Rest up in the budget-friendly Stratford Inn within sight of Grizzly Peak — and remember to pack your swimming suits to take advantage of the pool. Go retro-kitsch at The Palm’s quirky cottages, some of which include kitchenettes. Or stay a stone’s throw away from Lithia Park at the schmancy Ashland Springs Hotel. 

Catherine Ryan Gregory
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