Oregon's Cheery, Annual Christmas Festival Offers Tons Of Winter Holiday Fun

Europe is known for its Christmas markets, and for good reason. However, you don't need to pay a ton of money to travel overseas to experience a magical holiday wonderland. When the weather starts turning colder and every commercial features Christmas music, consider booking a trip to Jacksonville, Oregon, for its cheery and charming Victorian Christmas Festival, taking place every weekend from late November to Christmas.

Jacksonville is a small town of just under 3,000 residents as of 2025, but it goes all out for the holiday season. Originally populated by the Upland Takelmas Native American tribe, with the current town founded by miners who discovered gold nearby in 1851, Jacksonville is one of the coolest small towns in the America. It has some great shopping and dining, and it's the gateway to the Applegate Valley Wine Trail that takes you through 20 wineries in the area, all within 25 miles. Of course, you can also hit one or all of the seven tasting rooms right in town. Most of Jacksonville is a National Historic Landmark with lots of preserved buildings from the Victorian era, and its annual Christmas festival reflects that. There are costumed carolers, a historic home with tours that show you the way people of that era celebrated the holiday, and trolley rides to learn about history and to see the holiday lights. 

Jacksonville is only around 8 miles from Rogue Valley International Medford Airport. However, if you're flying into Portland International Airport, that's around 283 miles away, and you'll need a car. It's also not a bad idea to have some wheels if you're looking to explore the surrounding areas.

Jacksonville puts on all its holiday finery around the holidays, and the businesses and wineries have window displays and sparkling lights to celebrate the season. However, you don't have to walk around all night to check it out. Instead, take the town's Holiday Trolley Lights Tour, a 45-minute trolley trip around Jacksonville where you can see all the shimmering displays of festive cheer. Even the trolley is decorated. It runs every 30 minutes each night in December, other than Christmas Eve and Christmas Day, from 5 p.m. to 8:30 p.m. Tickets for the tour are $18 at the time of this writing, and they're limited, so make sure to reserve yours before your visit. In addition, you can purchase coffee or cocoa and bring it on board with you while you bop to some holiday tunes. You can also take the narrated history trolley tours for $15 on Saturdays and Sundays in December during daylight hours.

If you've got the little ones along with you for your Jacksonville winter vacation, they can get a picture with Father Christmas. The kids can tell him about everything on their holiday wish list, and you can take pictures for free. You read that correctly: There is no professional photographer there and no charge to take photos. You can find him at the U.S. Hotel at California and 3rd Street on Saturdays and Sundays. 

Jacksonville also hosts an annual tree-lighting ceremony in late November to start off the festivities, and Father Christmas makes an appearance in Jacksonville's holiday parade in early December. While you're shopping around town on the weekends, checking out the window displays, stop by the Jacksonville Chamber of Commerce where there will be carolers and bagpipers in period costume, as well as free hot apple cider to warm the cockles of your heart. You'll also see carolers around town. 

Make sure you don't miss a tour of the Beekman House, the Gothic Revival home built in the 1870s. During the holidays, you can get a tour from docents in period costume where you'll learn about the way Victorians celebrated the holidays. That includes a sample of some sugar cookies and a Christmas Bazaar (which is separate from the tour and free) to get a bit of your gift shopping done. Tickets for the tour are $10 for adults and $5 for kids 12 and under.

If you're hungry, stop by Back Porch Bar & Grill, which has been around for close to 40 years. It has Texas-style barbecue, burgers, and other hearty fare. You can also visit The Miners' Bazaar, a funky art house and cafe inside a house that's over 150 years old. You can do crafts, find souvenirs and gifts to purchase, have a drink, or try delicious dishes from the nearby Jefferson Farm Kitchen that are brought in, like meat or veggie shepherd's pie, cheese and meat trays, tuna melts, and mac and cheese. Finally, if you have your car with you, it's worth hitting the nearby Rogue River for some outdoor winter activities, around 20 miles away.