Hike of the Week: Hemlock & Pine Mountain

This wondrous hike actually allows you to explore both Hemlock Hills & Pine Mountain-- honestly, this was a bit accidental, but I find the best journeys are often those unplanned ;) My original goal was to find the high point with the lookout, which I had been told was off of Pine Mountain Road. The day was foggy & cloudy, so I knew I wouldn't get the best view, but at least I could scope out the hike before bringing the kids next time. (It's always nice when I'm not lying to them, "We're almost there-- it's not that steep!" when really I have no idea! We moms are notorious liars.)

So I found the small parking area up Pine Mountain Road, and when I say small, I mean small. I'm lucky no one else was there that day. There are no facilities either, so be sure to potty first! (Which I did, but I still had to relieve my full bladder in the woods, another reason I was grateful for no other hikers around! It's tough to be a girl.) Now, here's where I went wrong but oh-so-right: I took the obvious trailhead. The one right in front of me next to the big sign.

The trailhead, by the way, is stunning. Not all hikes are gorgeous right out the gate, but this one was. It's the yellow trail and it begins with a very gentle downward slope. On a quiet fall morning you can hear the echoes of acorns dropping like mini cannonballs. Don't take it personally-- I had to convince myself there were no maniacally-laughing squirrels up in the treetops just hurling acorns at me. I knew the woods wanted me there. So I continued.

Right at the start you will see some beautiful rock formations and curlicue trees, and immediately, you will know this hike is special. It is one you will want to return to again and again-- magical and mysterious. Movies should be made here. Seriously.

At .22 you'll arrive at a little wooden bridge-- stand here & listen. It is otherworldly. If you disagree, you have lived in CT far too long & take it for granted. Open your eyes and ears a little more, & you will recognize the fairy-tale-likeness of this spot. I have added it to my Favorite Spots on the Planet List.

At .32 you'll have to traverse large boulders! Be careful! Adventurous kids will love this part, but be sure they are cautious. Also, while dogs are allowed here, if your dog tends to be a puller (like mine), I'd leave him/her home, simply because dogs are more agile than we are & forget that a 2-footed clutz is behind the leash! On the other hand, pullers are great to have on steep climbs ;) And a steep climb is upon you at this point of the hike!

Once you arrive at the blue-yellow fork, stay on yellow. Also keep your eyes on those trail markers-- they can be spaced far apart. At .5, it gets swampy-looking. In the summer, I'd be sure to have generous amounts of bug-spray on. It's not swampy for long, as you arrive to what almost looks like a landscaped set of stepping stones. At .64, you have the option to go left onto yellow-blue toward Lake Windwing or go straight onto Blue. But for this hike, turn around at this point, because you still have the grand finale to get to, and that's at Pine Mountain!

I actually did go down both trails for a bit before I realized I was heading into a much longer hike than I anticipated that day. If you are hiking without kids, you should definitely explore these longer trails. The blue trail will eventually take you towards Miry Brook, where you could hop on the orange to the parking lot on Ned's Mountain. Had I continued on the yellow-blue (the online trail map has this as a brownish orange line, very confusing to a girl alone in the woods!) I would have ended up down by Lake Windwing on the first Hemlock Hills hike I blogged about! See, I'm beginning to get my bearings & see how all these trails and parks connect! But the internet was quite confusing.

Anywho, go back, staying on the yellow trail. If you're lucky like I was, you'll run into James & Ray, mountain bikers who I coincidentally ran into also on last week's Farrington hike! Great minds think alike I suppose. They were the ones to kindly tell me I had missed my intended trailhead! I asked how long the hike was to the looking point, and they said I could do it in 10 minutes. So once I made the return trip to my car, I dropped off my backpack, retrieved necessary provisions for being a girl in the woods who has to pee very badly, and crossed the street, where right behind my van was the trailhead I had come for! The true trailhead was a bit down the road with a wood sign, but I took what was closest and was also clearly a trail, though it had no marking. So it'll be a bit before you see the official yellow trail markings.

Luckily the mountain bikers were right-- the Pine Mtn. Lookout (also known as the Ives' Cottage location, though no cottage exists there & now I want to know the history here) was not too far. But it is a very good climb! Be patient if you have small hikers with short legs-- this is a sweat-inducing hike. But when you tell them it isn't that far, you are not lying ;) This hike isn't nearly as pretty as the Hemlock Hills, but the view is spectacular once you arrive! Rest here, take a lot of photos. I've heard this is one of the highest points in Ridgefield-- it's definitely the best vista I've found so far. On a clear day, you can see the Long Island Sound. But I didn't get a clear day. Still, it was incredible to be above the treetops. I can't wait to return when the leaves change color even more!

Had I only done this hike, I would've continued along the yellow to see the chimney ruin and do the loop. There are red trails that connect to this as well, which lead to Bennett's pond or even Wooster Mountain State Park. I love the infinite possibilities of these trails so close to home! Because these trails all connect, there can be a lot of confusion as to trail names. This Pine Mountain hike has also been called Bennett's Pond because it eventually connects there. However, it is pretty far from the actual Bennett's Pond & Bennett's is another hike (off Bennett's Road) that I have yet to blog about that I did with the kiddos. It wasn't my favorite, but it's worth exploring.

For this hike, the lookout is your summit, then you will return down. In total, this Pine Mountain portion is just .9, so add that to the Hemlock Hills portion (about 1.3), and that gives you a perfect 2.2 mile hike. Because you'll want to take a lot of photos and give your kiddos some breaks on that climb, plan for 1.5-2 hours. This really is my favorite so far!

As always, wear good athletic shoes, bug spray, and pack plenty of water & snacks! It may be wise to bring hiking poles for the steep downhill stretches, but they're not mandatory. Feel free to share your own experiences in the comments!

Hemlock Hills from Pine Mtn Rd

Every good hike has a wooden bridge

The beauty of Hemlock Hills

Rocky terrain of the yellow trail, Hemlock Hills

More Hemlock Hills stunning beauty

Look for this rock formation at Hemlock Hills

Pine Mountain Lookout!