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Ashland, OR: Winter Weekend Trip

There’s much more to this charming town than theater.

People snowshoe on a trail on Mount Ashland in the snow, image
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Photo: maciej / Shutterstock
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The area surrounding Ashland turns into a winter wonderland each year.

The small town of Ashland in southern Oregon is famous for the Oregon Shakespeare Festival—and rightly so. But visitors who head to Ashland on a winter weekend will find the festival between seasons. The good news is that there’s much more to this charming town than theater, and plenty to keep you entertained any time of year.

Outdoor Winter Fun in and Around Ashland

Wintertime family fun can be had without leaving town. Every year, Ashland’s lovely Lithia Park becomes the home of the Ashland Rotary Centennial Ice Rink. Dates vary, but you can expect the rink to open in mid-November and last through February. Adults skate for $4, kids under 5 are free, and skate rentals are just $2.50.

A mere 22 miles from downtown, Mt. Ashland offers skiers and snowboarders 23 runs over 220 acres. It’s been a local favorite for winter recreation for decades, providing equipment rentals in case you don’t have your own gear. There are 17 miles of trails for cross-country skiers and snowshoers of all skill levels at Buck Prairie, 13 miles east of town. Stop at the Ashland Outdoor Store for information about either ski area and to pick up any cold-weather layers you might need.

The sun turns the sky, snow, and lake yellow as it sets behind Crater Lake in Crater Lake National Park near Ashland, Oregon, picture
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Photo: Sky Cinema / Shutterstock
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The sun sets behind Crater Lake.

Table Mountain Snow Park, 28 miles west of Ashland, has the area’s most popular sledding hill. It’s steep and long, but there’s an upward slope at the end so it’s safe as well as fun. (Getting there requires 4-wheel drive, so take care.) For a day trip further away, head to Oregon’s only national park, Crater Lake, about 75 miles from Ashland for a free, ranger-led, off-trail snowshoeing excursion through the meadows and forests along the rim of Crater Lake.

Read More: A Romantic Getaway to Crater Lake National Park

Indoor Fun in Ashland in Winter

When it’s time to come in from the cold, Ashland has cultural appeals aplenty. The Schneider Museum of Art at Southern Oregon University, with exhibits that change regularly, is free and open Monday-Saturday.

Travelers visiting on the first Friday of every month can join locals from 5-8 p.m. on the First Friday Art Walk, when galleries open new shows and art lovers can meet the artists.

Kids of all ages love the interactive exhibits at ScienceWorks Hands-On Museum, and parents appreciate that kids are learning while they’re playing. Admission for kids ages 2-12 is $10, and it’s $12 for teens and adults. The museum is open Tuesday-Sunday.

Winter Events in Ashland

The annual Festival of Light Celebration kicks off the holiday season in Ashland on the day after Thanksgiving with Santa’s Parade, carolers singing downtown, and a chance for the kids to meet Santa for photos. Special weekend events continue through December, including caroling on Saturdays. Pick up an event schedule and a holiday gift guide at the Ashland Chamber of Commerce or at one of many local shops.

The fun doesn’t stop come January 1. Ashland is home to the Oregon Chocolate Festival, which occurs in February or March (depending on the year). There are chocolate tastings, demonstrations, and contests, as well as an expo floor full of chocolate purveyors from near and far.

A cake with a chocolate ganache and chocolate roll sit on a plate at the Oregon Chocolate Festival in Ashland, Oregon, image
Photo credit
Photo: Courtesy of Oregon Chocolate Festival
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Indulge at the Oregon Chocolate Festival in Ashland.

Ashland Eats

Visitors from all over the world come to Ashland for the Shakespeare Festival, and more than 100 restaurants in town cater to every taste. Look for local ingredients on menus, such as Rogue Creamery cheese made in nearby Central Point and Branson’s Chocolate made by a longtime Ashland resident.

Try the farm-to-table comfort food at Larks Home Kitchen Cuisine in the Ashland Springs Hotel, where they pride themselves on using ingredients produced nearby and knowing their farmers firsthand.

Smithfields Restaurant and Bar is proudly meat-centric, with a variety of steaks and a selection of house-made charcuterie on the menu. Located across the street from their Smithfields Pubs and Pies location, the steakhouse follows "nose-to-tail" practices and works with local providers to round out the menu with fresh seafood, produce, and beer.

Adults can warm from the inside out with a visit to one of the local wineries or microbreweries for a tasting. Standing Stone Brewing Company in downtown Ashland prides itself not only on its craft beers but also on its commitment to sustainability, social responsibility, and eco-friendly business practices. Stop in to sip their brews along with a menu featuring meat and produce from their own farm.

Or head to the Ashland Wine Cellar for a local wine flight to easily sample pours from several nearby wineries without leaving town.

Holiday Shopping in Ashland

Harry & David boxes are a staple of holiday gift giving, and you can take a tour of their factory or browse their extensive shop at the Harry & David Country Village about 13 miles from Ashland in Medford, OR. In town, Branson’s Chocolate is perfect stop for small gifts and stocking stuffers.

The Holiday Market, which spent 13 years in Ashland, moves to its new home at the nearby Medford National Guard Armory in December 2018. Shoppers can expect the same great selection of local artists and artisans selling handmade souvenirs and gifts. For November visitors, the Ashland Armory Christmas Faire runs over Thanksgiving weekend in the Historic Ashland Armory. Entry to both markets is free and there’s live music to entertain you while you browse for special goodies to bring home.

Up Next: Best Mountain Towns for Winter

If you're planning on traveling to Ashland, talk to the Vacation Experts for free at AAA Travel.

This article was first published in December 2018. Some facts may have aged gracelessly. Please call ahead to verify information.