Pillsbury Mountain is one of those peaks that is in the middle of nowhere, at least so it seems when you are driving there. A maze of backroads will get you there, but you need to take it slow as they can be very rough at times. Pillsbury is one of the Adirondacks 100-highest peaks.
How to get there
From the intersection of Route 28 and Route 30 in Indian Lake, follow Route 30 toward Speculator. Continue for just over 16 miles and turn right on Perkins Clearing Road on the right and follow it to Perkins Clearing, a T-Intersection. Take a right onto Military Road, then turn right at the Sled Harbor intersection to get to the trailhead.
From the trailhead you will descend slightly to cross the Miami River before starting your climb, which is steep out of the riverbank and then moderate for a bit. Some areas have tough footing and muddy tread to contend with, but all-in-all it's not too bad.
The trail leads to a ridge where views start to open up through the trees. The ridge mellows out and soon the fire tower appears. Small views can be had from the rocky summit area over the trees, but the best views are had from the fire tower's cab. The fire tower is open to the public. The observers cabin is near the tower.
1.6 miles to the summit
The Jessup River Road is closed during the winter making this a very long snowshoe approach. While you could ski the road to the trail for quicker access, plan on a much longer day with a trail that might be unpacked.
The trail section is not recommended for cross-country skiing.