About 6 miles
Add 1.5 miles for side trip

To get to the first trailhead, (the blue outlined loop on the map) head through the park from the Taconic and Route 301, down past Canopus lake (on your right) then back up and over the next hill. After a short while you'll see a widespot along the sides of the road where people have often pulled off to hike. THe only landmark there is a red survey cross on a rock outcrop on the right side of the road. Look for the trail maker for the RED trail and head towards the northwest...

This loop is wonderful. I've marked it out in blue on the map but it consists of several different trail segments of various posted colors. Some brief directions:

From Route 301 take the red trail west for just a few hundred feet - a yellow trail will come in from your left - watch for it and take it! If you miss it, turn this paper upside down and follow everything in reverse.

This trail traverses several short ridges with deep wet rocky valleys filled with mountain laurel and comes out in 15 minutes on an old woods lane. Follow the road to the left and then jog to the right, through the cattle gate and into the Hubbard Farm. When you reach the road turn left then right. If it's a hot day the huge trees here are a good place to rest. Go through the cattle gate and up and over the fields - be prepared for the views! Also, don't be afraid of the cows if they're in the field. They're big but they'll be seperated from their calves and the bulls will be elsewhere so they're big (didn't I say that?) but they're passive and may come over for a visit.

The yellow trail follows across this field, then through another gate, turns north and follows a hedge row and then across that field to the west and into several hay fields before reaching woods again at about 1.5 miles. Another thousand feet brings you to a rock outcropping with passive views across the Hudson and up the valley you'll be walking in later.

The trail after here drops down the mountain to a valley and follows the Clove Creek along a private road, crosses that road and joins another where it will meet the blue trail after a short while. Turn north eventually to a large pond. There is [was] a red survey flag in a tree where a short side trail leads to a rocky outcrop where you can sit along the pond and look up at the farm fields you were on an hour earlier. It's a very pretty spot.

The blue trail continues along the side of this lake and crosses an inlet stream then bends uphill - here you have a choice:

if you're still energetic bear off to the left and follow the woods road north (above and) along the creek otherwise...

... continue on the trail to a junction with a red trail and to Beaver Pond which is a nice place for a swim. At Beaver Pond you will have joined a red trail (Charcoal Burners Trail) - follow that back about one mile to the car.

If you opt for the north woods road (yellow outline on map) , this will go through some rather isolated back country where you're more likely to see bobcats, pumas and bears than people. It eventually meets up with the Blue Trail (the top most section of the trail you left just before) near the site of an old summer camp. You'll see its fields through the trees and it too is a nice place for a stop. Continuing on the blue trail to the north or east you will climb a ridge that becomes dry and xeric and typical of the highland uplands - if you're in time the blueberries will be everywhere so be ready eat. After reaching the ridge top the trail swings south and there is a nice open view eastward off the side of the trail. The trail continues until it meets the red trail I spoke about in the paragraph above.

I don't know the total length of this hike but I've done it and it took a long time so I'm guessing about 7 or 8 milesThe red trail turns left off the road at a high point after crossing a creek and begins a short but steep climb to the top of East Mountain with a nice view over Philipstown and to the Highlands Gap in the valley. The trail back down the other side is rarely traveled so watch for red markers or other obvious markers of human trail building activity (old sawn logs, etc.,) until it once again reaches Schoolhouse Road. Turn south and follow the road out and back to your car.