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Family-Friendly Destinations to Spend the Holidays Around Oregon
Family-Friendly Destinations to Spend the Holidays
written by Jean Chen Smith
Have you noticed there is a special energy that rolls around when the holidays approach? Maybe it’s just me, but I relish the warmth of twinkling lights, the joy of festive gatherings and the comforting sense of togetherness that fills the air. It is a time of family get-togethers and creating heartfelt traditions and memories.
It is also a great time for traveling and exploring, being fully immersed in the holiday season. From snow-covered mountains to cozy coastal towns, our state offers a magical mix of holiday destinations that are perfect for families. Whether you are looking to embrace the winter chill or enjoy festive small-town charm, here are some of the best family-friendly spots to spend your holidays in the state.
Powell Butte
Tucked into the high desert hills of Powell Butte, Brasada Ranch offers a family-friendly holiday experience that blends outdoor activities, cozy accommodations and festive events perfect for creating lasting memories together. With the majestic high desert landscape as a backdrop, the ranch offers a range of spacious accommodations designed for family comfort. The thoughtfully designed Sage Canyon Cabins provide privacy and convenience, with full kitchens, cozy fireplaces and private hot tubs. Larger groups will appreciate the multibedroom layouts that allow for togetherness without feeling crowded.
At the ranch, there is plenty to keep every family member entertained. Activities include swimming, biking, horseback riding, fishing, archery, crafts, hiking and a rotating calendar of special holiday activities. The property’s eighteen-hole championship course is open year-round, so even on winter days, it is possible to tee off under blue skies in the afternoon. While occasional snow may briefly pause play, the course’s elevation and climate make winter golf not just possible, but also surprisingly enjoyable.
The winter can also bring on some chilly weather, so for some indoor fun, the Athletic Center is a hit. Kids can burn off energy in the indoor pool or on the sport courts, while adults can sneak in a quick workout or a rejuvenating treatment at Spa Brasada, where seasonal massages and facials draw inspiration from the surrounding landscape.
And, of course, no holiday is complete without good food. The Ranch House serves elevated comfort food that is both locally sourced and family-approved. Think rosemary roasted chicken, warm apple crisps and handcrafted cocktails for the grown-ups. Many families even choose to spend Christmas or New Year’s Eve dining here, thanks to the ranch’s festive menus and stunning sunset views.
Medford
Looking for a holiday destination that blends outdoor adventure with the vibe of a small city? Medford offers the perfect setting for families to celebrate the season. Check in to the Compass by Margaritaville, a kid-friendly hotel featuring family rooms with bunk beds, an outdoor pool and a casual on-site restaurant with a kids’ menu. Guests can enjoy a complimentary breakfast buffet with their stay, which makes mealtime with little ones more convenient.
Nestled in the heart of the Rogue Valley, Medford is known for its crisp winter days, twinkling lights and easy access to nature. From ice skating and tree lighting events downtown to cozy cocoa stops along the Rogue Valley Food Trail, there is something for every age. Beautiful Crater Lake National Park, in its snowy glory, is open year-round and is about an hour’s drive away. Prior to heading out, make sure to check the National Park Service's website for accessibility due to inclement weather.
In the first week of November, Barnstormer’s Holiday Bazaar takes place at the Rogue X Complex. The two-day event is a huge shopping extravaganza of local crafters and artisans. Explore the rows of booths to find the perfect gifts for everyone on your list. Do not miss the Medford Winter Lights Festival, a free community event with live performances, which takes place on December 6 at Pear Blossom Park.
Known for the Oregon Shakespeare Festival, Ashland is a fifteen-minute drive away and definitely worth a stop. The town’s Festival of Light kicks off the season with a spectacular tree lighting and parade. Families can stroll through the decorated downtown, catch a family-friendly play or take a brisk hike in Lithia Park.
Portland
Located in downtown Portland, The Benson Hotel has one of the most festive holiday attractions in the city. The historic hotel lobby, with its wood paneling and marble floors, welcomes guests with vibrant, celebratory decor. The city’s annual gingerbread display, which has been a Portland holiday tradition for more than fifty years, will be on exhibit. An elaborate creation, notable for its size and intricate detail, is made entirely of edible confections. Prominent United States presidents have stayed at The Benson Hotel, including Dwight Eisenhower, John F. Kennedy, Richard Nixon and Bill Clinton.
Make reservations at G-Love for a delicious vegetable-focused meal. Although the casual restaurant does serve animal-based proteins, vegetables take center stage. Check out the winter menu, where the kitchen makes full use of the freshest ingredients of the season. The dishes are great for sharing and trying out new things, especially for little ones and picky eaters. Do not skip dessert—both the whip-a-licious passion fruit and storm cloud yuzu sorbet satisfy a sweet tooth.
Visit the Lloyd Center Ice Rink, which lies just northeast of downtown Portland, for some fun on the ice. The rink is located on the first floor of the Lloyd Center mall and is a popular gathering space for families and friends during the merry season. With a large decorated tree, food court and lots of shopping options, it is a one-stop destination for holiday cheer, good eats and great gifts.
Even in the winter, Portland’s surrounding natural beauty is accessible and family-friendly. Try a brisk walk through Forest Park, one of the country’s largest urban forests, or take a day trip to nearby Mount Hood for snowshoeing or beginner skiing. Closer to the city, Washington Park and the Portland Japanese Garden offer peaceful seasonal strolls with a magical touch—especially after a light dusting of snow. Ride the forty-five-minute Holiday Express train, powered by vintage steam locomotives along the Springwater Corridor, offering views of the Oaks Bottom Wildlife Refuge.
Hood River
An hour east of Portland, Hood River is a scenic town with easy access to snowy adventures on Mount Hood. Horsefeathers Boutique Hotel offers elegant condo-style living with fully equipped kitchens, gas fireplaces and private outdoor decks. Some rooms provide washers and dryers, which makes it convenient for guests to pack lighter.
Hood River is famous for its world-class windsurfing and kiteboarding; however, there are many things to do during the colder months. Kick off the season on December 5 with Hood River’s signature tree lighting and street festival. Enjoy live music, local food vendors and holiday shopping in the downtown area.
Book a ride on Mount Hood Railroad’s Polar Express Train Ride, where you can enjoy hot chocolate and cookies while being greeted by a cast of Christmas characters. The magical ninety-minute ride weaves through the scenic Hood River Valley and arrives at “The North Pole,” where Santa greets passengers of all ages.
Eugene
Situated along the Willamette River, the recently renovated Valley River Inn combines comfort and holiday charm for a picturesque wintertime visit. During the holidays, the hotel dresses up with twinkling lights, garlands and a towering Christmas tree in the lobby. Kids will love spotting the seasonal touches, and parents will enjoy the relaxed vibe. With more than 250 rooms and suites to select from, larger families will appreciate the extra space the suites allow. Additionally, there is a wide assortment of amenities for families, including a seasonal heated outdoor pool, fitness center and spacious terrace. The hotel’s restaurant, Sweet Waters on the River, serves breakfast, lunch and dinner.
Next door is Valley River Center, Eugene’s largest shopping mall. It is especially convenient for families looking to squeeze in some last-minute holiday shopping or take photos with Santa. The mall also has a movie theater, which is a perfect stop on rainy days. For more outdoor fun, the hotel’s direct access to the Ruth Bascom Riverbank Path System means you can bundle up and take a family stroll or bike ride along miles of scenic trail. You might even spot wintering birds along the riverbanks.
There are a variety of family-friendly events in Eugene during the holidays. The Holiday Market at Lane Events Center is a big draw—the indoor artisan market features handmade gifts, festive food vendors and live music. It is an ideal place to pick up gifts for loved ones, while supporting small, local businesses. Or catch a family-friendly concert or holiday performance at the Shedd Institute, which is located in a stunningly restored church building dating back to 1915.
Florence
Storm watching in the charming coastal town of Florence is a thrilling family-friendly experience best enjoyed during the winter months, from November through March. The educational experience is a great opportunity for kids to connect with nature, although you will want to choose safe viewing spots and keep a safe distance from the water. The winter period coincides with the king tides, which are the highest tides occurring naturally each year. It happens when the gravitational forces of the sun and moon align perfectly with the Earth, causing an extra-strong tidal swell.
Driftwood Shores Resort makes an optimal base camp because of its family-friendly features, such as spacious oceanfront rooms with kitchens and balconies with stunning views. The indoor aquatic center features a heated pool, a children’s wader pool with splash zones and an oversized whirlpool tub, providing fun and relaxation for guests of all ages. Don’t want to cook? No problem. Driftwood offers “Holiday Dinners to Go” through the restaurant, Surfside Bistro.
Visit historic Old Town for the Winter on the Waterfront Festival, featuring live music, refreshments, a vehicle parade, hayrides and shopping. It all leads to the culmination of the Florence Holiday Festival & Tree Lighting. The Winter Music Festival takes place in late January at the Florence Events Center, featuring various types of music, including bluegrass, open-jam sessions and more.
