Milwaukie, Oregon

Looking for the best chillin in Milwaukie? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Milwaukie. The detailed guides, photos, and reviews are all submitted by the Outbound community.

Top Chillin Spots in and near Milwaukie

  • Lyons, Oregon

    Henline Falls Trail

    5.0
    1.71 mi / 312 ft gain
    The trail is a washed out, old mining road making its way through a lush forest with a mix of ferns, moss covered trees, and towering Douglas Firs with trees blown over from wind storms lining both sides of the trail. I call those Big Foot traps. The trail comes to a fork, stay to the left you ar...
    Read more
  • Lyons, Oregon

    Cedar Flat and Kopetski Trail Loop

    9.62 mi / 958 ft gain
    On Saturday, I slid into the backseat alongside weekend belongings crammed in the car trunk. Backpacks with patches and streaks of dust. Bags of food that could be cooked over the flames of a fire. We drove south on the 5, leaving Portland and crossing through Salem, as Lake Street Dive albums p...
    Read more
  • Lyons, Oregon

    Swim at Three Pools

    5.0
    To get there from Salem, Follow Hwy. 22 east to Mehama. Turn on Little North Santiam Road (FS 2209) and proceed for 12 miles to Three Pools Day Use Area. Three Pools is by far one of the most popular swimming holes in the Northwest. With multiple swimming holes within just feet from one another i...
    Read more
  • Government Camp, Oregon

    Camp at Trillium Lake

    4.5
    The reflection of Mt. Hood on the lake makes this trip definitely worth the visit.Try to arrive during the day so you can watch the sunset. For photographers, the south side of the lake is an amazing spot to take photos, especially on a windless day. For those looking to kayak or fish, there is a...
    Read more
  • Government Camp, Oregon

    Snowshoe or Cross-Country Ski to Trillium Lake

    5.0
    3.6 mi
    Starting at the parking lot for Trillium Lake located right off of Highway 26, go past the locked gate and begin walking downhill. After about a mile, you will see a fork in the road. Either way will eventually take you to the lake, but going left will be much quicker and take you to the best spo...
    Read more
  • Government Camp, Oregon

    Photograph the Wildflowers at Timberline Lodge

    4.0
    From the mount hood scenic byway in Government Camp, Oregon turn on the road that heads up to the Timberline Lodge. Follow that road to the end and park in the lot all the way at the top. In the ski season you need a pass to park there, but if you go in June, July, Or August (aka when the wildflo...
    Read more
  • Clackamas County, Oregon

    Bike the Timothy Lake Trail

    4.5
    15 mi
    Located about 2 hours outside of Portland, Timothy lake is a great home base to adventure from. It has many campgrounds, lots of lake access and great loop around the lake that is open to both hiking and Mt biking. While the hiking loop is 13 miles, the Mt. bike loop is 15 since you need to make ...
    Read more
  • Stevenson, Washington

    Wind Mountain

    5.0
    2.5 mi / 1037 ft gain
    Once you reach the parking lot, walk down the hill and find the trail head, which is easily seen as it is marked. Begin your trek up the trail. The way up is pretty much all uphill, and is a great workout for the legs. You will walk through forests and over many rocks on the way up. As soon as y...
    Read more
  • Clackamas County, Oregon

    Camp at Timothy Lake

    4.5
    Timothy Lake is one very large, man-made lake in the heart of Mt. Hood National Forest, and can be considered one of the best summer camping spots in the area. With more than ten campgrounds to choose from, this area can accommodate almost every type of camping possible - everything from cabin re...
    Read more
  • Mount Hood, Oregon

    Kayak Laurance Lake

    5.0
    This lake is found about 25 miles south of Hood River, Or. $5 for day use and now other passes are accepted, just keep that in mind. There are camping sites all over the lake as well, so if you are thinking of making a weekend out of it.  It wasn't very crowded on a weekend during the summer so y...
    Read more
  • Government Camp, Oregon

    Camp at Clear Lake

    4.0
    Located just 1.5 Hours from Portland and on the east side of clear lake, this campground offers multiple water activities such as Kayaking, SUP, Fishing, and Swimming. What's great about this campground is that the sites are large and are shaded by the old growth trees which makes it feel more s...
    Read more
  • Hood River, Oregon

    Punchbowl Falls

    4.5
    0.42 mi / 92 ft gain
    Getting to Punchbowl Falls is a super quick hike to a fun cliff-jumping swimming hole and waterfall. Be careful hiking the steep trail to the falls. Make use of the rope. Be VERY careful approaching the edge of the cliff higher up and know your limits when it comes to jumping. Always walk down a...
    Read more