This 4000 footer is great to start winter hiking on because the trail is usually broken in well and the view at the top is amazing!

The hike starts across the street from the AMC Highland Center on route 302, which means there is plenty of parking and when you finish there is a fireplace and snacks to warm up with! It starts at the Webster Jackson trailhead and after 1.4 miles breaks off onto the Jackson trail. At that point you could take the Webster trail to create a loop that summits Webster and Jackson, but after the 3 feet of recent snowfall, the trail had not been broken in very well to create the loop. If the conditions were better, reaching both summits would add an extra 1.1 miles to the overall distance. 

The Jackson trail continues up another 1.2 miles to reach the summit of Mount Jackson, which provides 360 degree views of the surrounding mountains, including an unbeatable view of Mount Washington (especially on a clear day)! The trail itself gradually gains elevation during the first 2.4 miles, and then the last 0.2 miles is incredibly steep. Make sure you are comfortable using snowshoes and following a trail because it can definitely get dicey at the end.The snow pack underfoot was over 4 feet deep and the trail itself is difficult to keep track of. We ended up wearing snowshoes the entire way, but conditions in the whites can change quickly, so I would recommend also having crampons because normally the summits get extremely icy.

The trail up Jackson also breaks off to Elephant Head near the beginning, which is 0.2 miles off the trail. We didn't take the time to check it out, but it would be an easy side trip!

After the hike we stopped in North Conway at Moat Mountain Brewing for some well deserved beers and burgers!

For a summer hike, check out Hike to the summits of Mt. Jackson and Mt. Pierce

Pack List

  • Snowshoes and poles
  • Crampons
  • Base layers
  • Down coat
  • Rain coat (on a sunny day at lower elevation the snow will be melting off the trees, which was essentially like walking in a rainstorm)
  • Camera
  • Snacks
  • Water in insulated water bottles (it will freeze in a camelbak)
  • Warm gloves
  • Toe/hand warmers
  • Small butt sled (the trails were in perfect condition for sledding down!)
Show More
RT Distance 5.2 Miles
Elevation Gain 2300 Feet
Activities Chillin, Photography, Snowshoeing, Hiking
Skill Level Intermediate
Season Winter
Trail Type Out-and-Back
Dog Friendly
Easy Parking
Family Friendly
Food Nearby


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