5 of the Best Winter Activities in Ashland, Oregon

From cross-country skiing to winery tours, there are so many ways to cure your winter weather blues in Southern Oregon. Read on to discover five of the best winter activities in Ashland, and if you are looking for more ways to brighten the holidays, simply unwrap our free Ashland Vacation Guide. Our carefully crafted guide is full of recommendations on Christmas shopping, award-winning restaurants, winter celebrations, and more!

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The Best Ashland, Oregon, Winter Activities

Stay Active

As the excitement of the Oregon Shakespeare Festival comes to a lull and the season ends, Ashland takes on a new face. Watch as the landscapes transform with powdered slopes and frozen waterways, making Ashland a premier destination for cross-country skiing, ice skating, snowshoeing, and more. While you may be tempted to hibernate for the winter, we encourage you to get out, stay active, and take advantage of what the season’s snowy weather offers. These activities only come around once a year, so enjoy them while you can!

Take a Winter Winery Tour

Wine tasting is one of our favorite activities throughout the year. However, winter offers visitors the opportunity to discover Southern Oregon for a quieter perspective. Enjoy a leisurely tour of the wineries in the Upper Rogue Valley and Bear Creek. Both of these wine regions are less than 30 minutes away from Ashland. If you’d prefer to stay in the city, there are many exceptional wine tasting rooms in Ashland. Come for the winter, and we guarantee you’ll find a blend you’ll want to sip all-season-long!

Complete Your Holiday Shopping

During your winter vacation in Southern Oregon, why not complete your holiday shopping? Locally made products always make the best gifts, and you will find plenty of unique, boutique shops to browse in downtown Ashland. Whether you are searching for handmade jewelry, authentic artwork, or home and garden decor, you will find a little bit of everything here. In addition, you can look forward to seeing much of the town glowing with festive lights and beautiful displays.

Indulge at the Spa

Snowy weather can often leave skin feeling irritated, and holiday stress paired with winter sports can take a toll on the body. These are a few reasons why a trip to the spa is so important. Deep-tissue massages, holiday manicures and pedicures, and hydrating facials are crucial in looking and feeling great throughout the season. Luckily, when you plan a trip to Ashland, you will find plenty of luxury spas nearby. For a full list of spa recommendations, remember to download your free Ashland Vacation Guide.

Celebrate the Season

Ashland hosts a handful of events throughout the season. From the Festival of Light Parade in November to the opening month of the Oregon Shakespeare Festival in February, there are plenty of reasons to smile when you attend any of the area’s fun, winter events!

Relax & Unwind at Country Willows B&B Inn

After a day of enjoying the best winter activities in Ashland, head home to our elegant bed and breakfast for a cozy night in. Grab your favorite book and snuggle The fireplace and couch in the Creekside Suite at Country Willows B&B Inn. up by the fireplace in The Creekside Suite. This elegant accommodations features a California king-size bed, living room with fireplace and television, and free high-speed internet. You can also enjoy an array luxurious amenities, including daily, farm-to-table breakfast, onsite hiking trails, and access to our outdoor, heated pool.

If you are ready to plan your winter vacation, check out our seasonal specials and book your stay. We can’t wait to host you at Country Willows B&B Inn!