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Caleb's Peak in Kent, CT. offers a nice woodland hike with some scenic views of the surrounding country side. Located on the Appalachian Trail just north of Kent center, Caleb's Peak is the kind of spot where you can sit back and relax after taking in some great views of the valley and mountains that shape the town of Kent. In addition to the great views, the trail takes you through some dense woodlands where you'll see old stone walls and remnants of farm life from years gone by. It's hard to believe that a few hundred years ago the forest in this region would have been all farmland and nearly void of any trees! If you take a close look at the width of the trees you'll notice that there are very few giant trees left (like oak or elm). As far as accessing Caleb's Peak, you have a few choices. For something a little challenging, you can hike up from St. John's Cliffs or from the Schagticoke Road/Kent School region. For a short alternative, you can drive up River Road from Kent School and park along the side of the road at the Appalachian Trail marker. From here it's a fairly easy hike to Caleb's Peak...but it would be a steep hike for those who are new to hiking...but very doable for anyone taking their time and not pushing themselves too hard.
The St. John's access is an interesting option in that you'll have to drive down a long, bumpy dirt road near Housatonic River to get to the trailhead (if you've got a brand new car or one that you like to keep in perfect shape, this may not be a good option for you...although you could park your car at the beginning of the dirt road and hike the one and a half miles to the trailhead). About one and half miles down the dirt road on the left side is a dirt parking lot. This is the trailhead for St. John's Cliffs. St. John's is a popular destination since it offers some of the best rock climbing in the state and is a good jumping off point for overnight camping along the Appalachian Trail. Don't be surprised if the parking is crowded...especially summer weekends. If there is overflow, just park along the dirt road far enough off the road so others can pass by. The hike up St. John's is steep and at times you'll have to use hands and feet to scramble up rocks. A few spots could be a little scary for those who don't like sheer drop-offs but it's more of a visual effect made by the cliffs; the actual trail is steep at times but not dangerous. The trail is well maintained and planned in a manner that takes you around the cliffs rather than straight up them. One thing is certain, you need to be in pretty good shape to hike up St. John's Cliffs...this would be a workout! Once you've gotten to the top of St. John's, take a break and check out the scenery. After resting, follow the trail as it goes up and to the left, eventually taking you over to Caleb's Peak. There are some nice eastern views as you proceed towards Caleb and the the peak area has a great southern view with plenty of space to find a spot and relax.
Schagticoke Road/Kent School to Caleb's Peak is a long hike but perfect for those who like to get out for extended hikes. As long as you bring water and lunch, the hike is challenging but not too bad. For someone in great shape, the round trip hike would be a good workout and an afternoon well spent (about 8 miles round trip). Start out at the Schagticoke Road/Kent School area (click here for Shagticoke description and directions). You'll go across some farmland, up a short and fairly steep climb, and along the ridge top that rises above Kent center. Along the way there are some nice views and a good woodland hike that's quite peaceful at times. Eventually you'll descend off the ridge top and come upon River Road. Crossing River Road and following the Appalachian Trail back into the woods, it's a short hop up the next mountain to Caleb's Peak. This option is a long round-trip hike but it's a great one for peace and quiet. The thick woodlands that dominate, kind of force you to be alone with your thoughts or have a good conversation with your hiking partner(s). The views that appear along the way break up the woodland hike and create some highlights that you'll likely remember for a long time.
Last, but certainly not least, is the River Road option
to Caleb's Peak. It's the easiest of all the options and a great choice
for those who love nice views but don't like (or can't do) strenuous
hikes. Directions: When you arrive in Kent you'll go west on Route
341. A half mile up 341 a bridge spans the Housatonic River at Kent
School. The very first right after the bridge, take a right
onto River Road. Set your odometer back to zero. 1.7 miles
later up River Road the Appalachian Trail crosses here. Park in the small
dirt cutout or along the side of the road where you see the white hash marks
signifying the Appalachian Trail. Go right, following the trail into the
woods as it rises steeply and on up to Caleb's Peak. It's a short but
challenging little hike to the peak but very doable for anyone.
Directions to Schagticoke If you want to tackle the Schagticoke Road option, don't take a
right onto River Road but drive another half mile on Route 341 to the intersection
of Schagticoke Road and Route 341. On your left will be a dirt cutout that is
parking for Appalachian Trail hikers. Across the road is some farmland. Follow the
Appalachian Trail over the farmland and into the woods. Proceed to Caleb's Peak's.