Top 16 Winter Adventures

Winter in Southern Oregon is the time to enjoy skiing on snow-covered mountains, ice fishing on frozen alpine lakes, fly fishing on rushing rivers, storm watching on the wild coastline or sipping wine by a warm fireplace. Southern Oregon provides winter activities for everyone and here are some of our favorites.


Start your winter with the magic of Victorian Christmas in Jacksonville. This historic gold mining town is full of character all year round, but when Jacksonville gets dressed up for the holidays it’s magical. Celebrations begin with the town covered in white lights, a tree lighting ceremony, carolers dressed in period costumes, warm cider & cocoa, narrated trolly rides, Father Christmas, tours of the historic houses and an old fashion Christmas parade attracting over 15,000 spectators. For Details.


There’s nothing quite like the experience of driving up into the snow-covered Cascades or Siskiyou mountains to cut your own Christmas tree. It’s a fun family tradition that provides excitement, fresh air, and an appreciation for nature, and the best part is you only need a saw and a $5 permit. You can purchase a permit can be purchased on-line from the U.S. Forestry Service or BLM or in person at Blackbirds or the store at Lake of the Woods Resort. With the permit you will receive a map of areas to go, and because 24% of Oregon is National Forest, you’ll have lots of choices. Make a day of it and go explore the mountains in the winter. https:/ or http:/ For Details and to buy permits online.


With majestic views of the surrounding natural beauty, Mt Ashland provides terrain for skiers and riders of every ability. Offering fun steep terrain, tree glades, 44 runs, five lifts, night skiing and 240 acres of skiable terrain. A cozy Alpine lodge with rental shop, retail store, ski school, lounge, and several dining options. Make it a weekend getaway and stay at Callahan’s Mountain lodge, only a few minutes away, they offer ski & room packages. For the more adventurous you can cat ski Mt. Bailey from Diamond Lake lodge, which has been ferrying powder hounds into the backcountry since 1977. With an impressive average yearly snowfall of 600 inches and some of the lightest and driest snow on the west coast. Cat Ski Mt. Bailey operates on 6,000 acres of varied terrain ranging from glades, bowls, steep chutes, and everything in between. For Details. For Details. For Details.


The Applegate River is one of the best kept secrets in Southern Oregon, it’s a 51-mile-long tributary of the Rogue River, 8 miles from Jacksonville and easily accessible with the best parks being Cantrall Buckley County Park, Applegate Lake, and Jackson Campground. Open for hatchery steelhead fishing Janury 1st to March 1st. Use of bait allowed. No angling from a floating device. For Details.


Ashland Rotary Centennial Ice Rink, located in Lithia Park delivers frozen fun for all. Ice skating & figure skating lessons offered. For Details. Or you can skate at the Olympic-sized Bill Coller Ice Arena in the Running-Y resort in Klamath.


Crater Lake is most popular during the Summer, but in the Winter, it is magical. It’s known as one of the snowiest inhabited places in North America receiving an average of 43 feet of snow per year. With stunning views of the lake, and 183,224 acres of backcountry to explore, this is one of the top destinations for winter explorers and offers guided snowshoe tours every Saturday and Sunday, November through April. The snowshoe hike is 1-2 miles off trail on moderate to strenuous terrain and is open to ages 8 and up with or without snowshoe experience. You can even camp along the rim in the winter with a valid permit. Mt Ashland is another great place for snowshoeing/cross county skiing. Drive just past the Ski resort to the final parking lot where the road ends (Hwy 20), park in that lot and you’ll see the beginning of the trail. Diamond Lake is also known for cross county skiing. Check all the websites for weather conditions before you go. For Details. For Details.


There is no faster way to explore the winter landscape of the Cascades than snowmobiling and Diamond Lake Resort is one of the few resorts that rents them. There are miles and miles of groomed trails, and you can ride all the way to Crater Lake National Park. Rates run from $300 per machine for two hours to $575 for all day + fuel. For Details.


Every Super Bowl weekend you can experience a kite festival on Lake of the Woods. Walk out onto the frozen lake and under the huge professional colorful kites as they take to the skies. Kites are made to look like giant animals, cars or spinning wheels. Check the cameras on the resorts website to make sure the weather is clear enough to fly the kites. Don’t worry, if you’re a football fan there is a giant screen set up outside, next to a warm firepit at the resort as well as screens inside the resort that broadcast the Super Bowl. Before you go, make sure you check the L.O.W’s resort website for weather conditions, as it can be too stormy for the kites to fly For Details.

The Kite Festival has been cancelled for February 2024 due to our exceptionally warm winter that has kept the lake from freezing.


Upper Klamath National Wildlife Refuge is part of a complex of six National Wildlife Refuges in the Klamath Basin whose combined mission is to protect what remains of what once was the largest wetlands area west of the Mississippi River. This amazing scenic refuge plays host to up to 1.8 million birds at a time. Many of those are waterfowl migrating on the Pacific Flyway such as geese, swans, and ducks but the refuge also plays host to large birds of prey such as hundreds of bald eagles, red tailed hawks, and rough legged hawks. Other birds frequently seen in winter and early spring are white-faced ibis, sandhill cranes, herons, egrets, cormorants, grebes, white pelicans, quail, and pheasant.

This refuge is free to visit and can be traveled by car, where you can cruise along at a few miles per hour taking in the abundance of awe-inspiring birds of prey while drinking hot coffee and blasting the heater. The best time to visit is in the months of February and March. This is one of the most beautiful and awe-inspiring winter landscapes in Southern Oregon so don’t miss it. For Details.


Jacksonville is the hub for the Southern Oregon Music Scene. Known mainly for the summer Britt Festival, but the live music continues all year long. Top places for live music are the Bella Union where on Thursday nights you can have live music with Oysters & Ale, then live music on Friday and Saturday nights. South Stage cellars offers dinner with live music in a cozy atmosphere with a warm fireplace on Wednesday nights, then live music again on Friday and Saturday’s. New this year is world class Classical Music playing upstairs at the Jacksonville City Hall. See their website for concerts in January, February, and March.,,


Winter brings frozen Alpine Lakes and Ice Fishing. The best place to fish is Lake of the Woods, where the resort rents everything you need including an Ice tent to keep you warm. You can rent an augur to drill the hole in the ice, or they will drill it for you. For Details.


There’s something truly magical about the Oregon Coast during the winter. For some it’s the howling sea; for others the crashing waves, or the warmer temperatures. The winter weather in Brookings is typically 10 degrees warmer than Rogue Valley, which makes winter a great time to visit. The best place to visit is the Samual H. Broadman Scenic Corridor which runs 12 coast hugging miles north from Brookings. This stretch of highway features one turnoff after another, each with access to picnic areas, viewpoints and trailheads that connect an 18-mile segment of the Oregon Coast. For Details.


The best location to go tubbing is Diamond Lake. You can rent a one or two-person custom tube but make sure you buy your tickets on-line. The fun starts with the ride uphill on the 470-foot-long wonder carpet conveyor to the top of the hill where you will find multiple lanes to slide down. This is fun for all ages. Other great sledding areas are Grouse Gap Sno-park past the ski resort on Mt. Ashland, Table Mountain Sno-Park by Hyatt Lake, and Farewell Bend Snow play area on Hwy 62 on the way to Crater Lake. For Details. For Details.


Southern Oregon is populated with hundreds of beautiful wineries that you can visit year-round. This is a chance to see some of the most beautiful landscapes around while enjoying a glass of wine, great food, and often live music. It’s not about the wine, it’s about the total experience, and being able to enjoy an afternoon at some of the most beautiful locations imaginable. Our favorites are:

  • DANCIN for the atmosphere, best wine, great food, and stunning vistas of the west hills.
  • Red Lily Vineyards for its location along the majestic Applegate River, Spanish wines, and good appetizers.
  • Parkhurst Cellers for its one of a kind 5-star appetizers and food pairing.
  • Belle Fiore Winery for its opulent, Napa Style facility, great food and views of its vineyards and chateau.
  • Dos Mariposas Vineyards for its family friendly atmosphere and its Lavender farm.
  • Rellik Winery for its great food, Alpaca farm and live music.
  • Schmith Vineyards for its extensive landscaped grounds, ponds, and great gourmet pizzas.
  • Hummingbird Estate for the beautiful estate it’s located in, and the amazing views of the Rogue Valley.
  • Woolridge Creek Winery & Creamery with its quaint location, house made artisan cheese and unparalleled mountain views.
  • Roxy Ann Winery, located on 200 acres in the 1900’s Medford Hillcrest Orchard Estate, offers a family friendly environment and live music every Friday and Sunday.
  • Cowhorn Vineyard & Garden, great biodynamic wines, amazing scenery, and woodfire pizza. Their gardens provide ingredients for Cowhorn Kitchen which is their restaurant in Jacksonville.
  • Naumes Suncrest Winery, located in a farmhouse of an old pear orchard owned by the Naumes family for over 100 years, provides great wines and panoramic views of Mt Ashland and the Siskiyous mountains.
  • Edenvale Winery, located in the iconic 1885 Victorian Voorhies Masion, they produce classic wines, estate-grown pear cider and are the venue for many memorable events.

Southern Oregon has three major mountain ranges, so the hiking opportunities are unlimited. In the winter, the Rogue Valley and lower sections of the Applegate Valley are usually free of snow, allowing for great hikes. Our winter favorites are the Jacksonville Woodlands, RoxyAnn Peak, Table Rocks, Forest Park, and the East Art Trail off Sterling Creek. In the winter you will find fewer hikers, raging waterfalls and swollen creeks, and the loss of the Oak and Maple leaves provide for many sweeping views.


Southern Oregon is unusual in that it has so many live theaters for year-round entertainment. Seeing a play live is a wonderful way to enjoy a cold and rainy winter day. One of our favorites is the Oregon Cabaret Theater, located in an old church in Ashland. It’s a small dinner theater that puts on well-done plays, often musicals or comedies. They offer entertainment all year long and currently they are playing “Clue” based on the 1985 movie. The dinners are as good as the plays. The Camelot theater in Talant is also open all year providing plays that are often musically oriented, currently on-stage is a spotlight on Sonny & Cher.

The most well-known and impressive theaters are the three that house the Oregon Shakespearean Festival which begins its new season in March and ends in November.,, For Details.

Remember to check the weather forecast before enjoying the outdoors. The winter weather in Southern Oregon varies from day to day, so make sure you are prepared.