Oregon’s Top 5 Uncommon Places to Go this Winter

Whether you’re looking for a skiing adventure or a counterculture getaway, these towns are our top five picks for winter destinations in Oregon.

Sunriver: Skiing and Entertainment

Sunriver Resort

Originally constructed as a resort destination in 1969, Sunriver has grown into a community with a year-round population of 1,400. Nestled among the trees at the base of Mt. Bachelor, the snow that usually stays throughout the winter months provides an idyllic winter atmosphere. In the village, families can test out their skating skills at the outdoor ice rink, then warm up with a warm cider or hot chocolate at Goody’s or one of the nearby cafes and bakeries. The village also has many local shops to explore, including places to rent snow equipment if you didn’t bring your own. Adventure lovers have close access to Mt. Bachelor and Hoodoo ski areas, while those who are more interested in the just playing in the snow can choose one of the many snow parks on the mountain.

Where to eat

Sunriver Brewing Co. | 57100 Beaver Dr. |

Village Bar & Grill | 57100 Beaver Dr. |

Where to stay

Sunriver Resort |

Ashland: Counterintuitive

While Ashland is known for hosting the annual Oregon Shakespeare Festival, the city offers plenty to experience in the winter. From Thanksgiving to New Year’s, Ashland hosts the annual Festival of Light, with a parade and live music performances throughout the season as well as an outdoor skating rink. If you are looking for alpine adventures, local ski destination Mt. Ashland offers twilight skiing on weekend nights, though snow has been tougher to come by in recent years. When you’re done playing in the snow, there are three craft breweries and seven local wineries and vineyards in the city. If you’re there in February, you can also catch a play, since OSF’s season begins that month.

Where to eat

Deux Chats Bakery | 222 A St. |

Swing Tree Brewery | 300 E Hersey St. #7 |

Where to stay

Green Springs Inn & Cabins | 11470 OR-66 |

Baker City: My Own Private Oregon

Baker County

Anthony Lakes Mountain Resort is farther afield (for most people) than other Oregon ski resorts such as Mt. Hood and Mt. Bachelor, but that just means you won’t have to battle the crowds to enjoy the slopes. The one-chairlift resort has the highest base elevation of the state at 7,100 feet, and it’s less than an hour away from Baker City, another favorite winter destination. The charming Eastern Oregon town of around 10,000 people is on the National Register of Historic Places. One of the best ways to view the whole town is to catch a sleigh ride that takes you through the historic district.

Where to eat

Lone Pine Café | 1825 Main St. |

Paizano’s | 2940 10th St. |

Where to stay

Best Western Sunridge Inn | One Sunridge Lane |

Depoe Bay: Coastal Cozy

photo by Ron Miller |

Oregonians don’t skip out on the beach just because it’s winter. One of our favorite coastal getaways is Depoe Bay, known as the capitol of whale watching on the coast. It’s also known as the world’s smallest navigable harbor. In late December and early January, you’ll have the best chance of spotting whales as they migrate south along the coast. At the height of seafood season, winter is the perfect time to try the fresh catch at local restaurants. When you want to warm up, Depoe Bay also has art galleries to explore.

Where to eat

Tidal Raves Seafood Grill | 279 NW US-101 |

Side Door Café | 6675 Gleneden Beach Loop, Gleneden Beach |

Where to stay

Whale Cove Inn | 2345 US-101 |

Joseph: Outback Extreme

Joseph is most often visited in the summer, but the small Eastern Oregon town is just as wonderful as a winter destination. Eagle Cap is Oregon’s largest wilderness area, with 556 square miles to explore by Nordic skiing. One of the best times to visit is at the end of January, when the community hosts the Eagle Cap Extreme, a dog-sledding competition that is also a qualifying race for the Iditarod and Yukon Quest. Enterprise is a ten-minute drive from Joseph and is home to a community ice rink. Skating is free, and local businesses rent out ice skates if you didn’t bring your own. If your family is new to skiing, the Ferguson Ski Area is a fun place to learn and close to the town. Spend the morning in the snow, and then head back into town for a warm lunch.

Where to eat

Old Towne Café | 8 S Main St. |

Where to stay

Wallowa Lake Lodge | 60060 Wallowa Lake Hwy |


A previous version of this article stated: “Eagle Cap is Oregon’s largest wilderness area, with 556 square miles to explore by Nordic skiing or snowmobiling.” Snowmobiling is prohibited in designated wilderness areas. We apologize for the error.

A previous version of this article listed Vali’s Alpine Restaurant and Delicatessen in Joseph in the “Where to eat” guide. The restaurant is closed during the winter months. We apologize for the error.

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