Hike #1488; Gaylordsville/New Milford Loop

Hike #1488; 6/6/22 Gaylordsville New Milford Loop with Kirk Rohn, Diane Reider, Mary F, Jim ? and Pam ?

This next one would be a return to an area I had not been in years, a series like so many others that I had walked away from and occasionally have the thought to return.

This would be the Housatonic Range series.

We had done the Appalachian Trail as a series in Connecticut, which pretty much all runs through the Housatonic Valley, and covered all of it in Connecticut. Then, we covered all of the former Appalachian Trail, now known as the Mohawk Trail, through the same area.

After completing that, we continued to the south.

The Housatonic Range Trail is one of many blue blazed hiking trails maintained by the Connecticut Parks and Forests Association. I had done so much of this system, and I absolutely love these trails.

 They’re always exciting and diverse.

My first hike south from the AT was one I’d put together from the Herrick Trail. This trail breaks off of the AT into the Herrick Trail Preserve, owned by a non profit. It was great, and then a short walk into the little town of Gaylordsville brought us to the start of the Housatonic Range Trail.
My plan for his had been to head far to the south, but it ended up running too long and we had to cut out early. The trail was far more difficult than anticipated as well, but I wanted to give it another go.

This time, I planned on a hike that would do the side trails from Housatonic Range, alternate routes, and then loop back to the same place by using the New Milford River Trail and the Sega Meadows.

On the previous hike through the area, we had lunch at the Gaylordsville Diner, and the parking lot was really big. I decided that this would be the best place for us to start and end a hike in the area.

Joining us this time were two newcomers, Jim and Pam. It’s always interesting when you get new people out on a hike, because you just never know what they’re going to think of our out of the ordinary style.

After meeting at the diner area, at a little strip mall, we started walking to the south a bit. 

I figured we could try to walk out of the strip mall in the back where we had the last time we walked through. This didn’t go as planned really because there wasn’t a good way through. We ended up in a sort of contractor’s area and there was a guy operating a machine. I stopped and asked him if there was a way through, and he confirmed we could walk through out the back. This brought us easily out onto Gaylord Road.

There was almost immediately points of interest, starting with the historic Gaylord School House on the right, built in 1740, now a private residence. 

We pushed just a little further ahead, and the Gaylordsville Cemetery was on the right, with beautiful giant white pines in front.

Just a little past this point, the Housatonic Range Trail goes into the woods on the left. We cut in here, descended a bit, and then crossed over the Morrissey Brook on a foot bridge.

The trail started climbing pretty much immediately on the other side via switchbacks.

I didn’t remember just how steep and crazy this trail was, and I thought maybe I could have gotten the stroller through on this, but there was no way.

Pretty soon, we skirted the north end of Strait Rock, a crazy rock outcropping. The foot way also got very difficult, more so than I remembered.

We went to the east of the rock, then climbed very steeply to the top of it. In a stand of pines, we got a bit of a view to the north where we could see the strip mall the Gaylordsville Diner was in. Things leveled off on the ridge top from this point for a while.

I pretty much hit it off with Jim when we started talking. We talked trail and such like most people do at the start, but then we started getting into it about food. It turns out he’s as much of a food fanatic as I am, and he immediately started in it with Pam that she always says he’s the only one that talks like that. “See Pam, it’s not just me!” and she said something to the effect of stopping encouraging him.

The mountain laurel was beautifully in bloom at the top of this slope, and we meandered along on a very pleasant route to the south.

We came out of the very nice woods onto Squash Hollow Road. Here, the Housatonic Range Trail turns to the left for just a bit, and then turns right again to climb further to the south and east.

We continued to the south a bit more, and pretty soon we came to the intersection with the Tory Cave Side Trail. When I was here before, we just continued on the Housatonic Range Trail south and didn’t bother with this because it would add to much. This time, I factored it in.
We turned left down the hill, and reached another side trail to the right which would be our return route back up to the top. We had to descend a bit more to reach the Tory Cave below.

The Tory Cave is a marble solutional cave, said to have provided a hiding place for a tories during the American Revolution.

This is the only "true cave" In Connecticut. While there are a lot of caves, they are otherwise rock pile caves with crevasses, not something that goes back into the mountain like this one.

The cave is now closed and gated to protect bat population. We went down to have a closer look at it, and I had assumed it was going to be shut, so I wasn’t all that disappointed, but I was glad to have seen it anyway.

We made our way back up, to the previous trail we had seen, and turned left to follow it for a bit along the lower part of the mountain. This actually saved us a bit because the main trail goes to the top of Boardman Mountain just above us, and the side trail bypasses it. We didn’t really have to climb any more from this point, and reconnected with the main trail again just to the east, where the two come back together.

There was a trail marker post that had been in the ground in this area, and then was pulled out.

However, they did something really creative and cut a notch in a dead tree about six feet high, and jammed the post into it with the trail sign hanging from it. As a trail maintainer myself, I really get a kick out of this stuff.

The trail got a bit more complicated ahead. There were signs saying that the trail was closed ahead. It used to come out to Everwood Drive to the east, but apparently a private land owner built a house where the trail had come out, so it was now necessary to dead end or lollipop loop back on a new connection.

I had figured out a way around this when I was there last. We had used aerial images and GPS and bushwhacked through the woods to reach a water tower to the south. 

We did the exact same thing we had done the last time, only this time there was a bit more undergrowth because it was the Summer.

I watched my GPS closely, and we made our way down a somewhat steep slope. When it turned into a bit of a shelf of land, we turned to the right, and I got on the right trajectory to reach the clearing for the water tower.
Soon enough, we reached the water tower, and then went around the fence enclosure to the left to reach the access road for it.

We followed the access road downhill, and it brought us out to a dead end road known as Twin Oaks. We took a break in the grass and shade there for a little bit.

When everyone was ready to go, we simply cut through the weeds to the west, and it was a slight slope down to Everwood Drive, but not so near the houses. We turned right on Everwood, headed up a slight hill, and then the trail went into the woods on the left side just ahead.

It was an incredibly green scene through these woods, with puncheons over wet areas and lots of skunk cabbage.

We headed up a bit and crossed Squash Hollow Road again, then headed further into the woods where there was a bit more climbing. We passed through stone rows, and there was a side trail to the left I don’t recall seeing last time. This was a bypass trail that missed going to the next point of interest, the Suicide Ledges.

We climbed back and forth up a slope, and came to a slight view on a rock outcrop where we could see Pine Knob to the south. The trail would take us there pretty soon.

The trail continued along the top of the big rocks, and then abruptly turned left to pass through the cave portion.
Some of the aforementioned rock pile caves are at the Suicide Ledges, and the trail descends into them. I actually went down through one and came out of it the wrong way because I missed seeing some blazes, but it was still cool.

We skirted around the big boulders, and then began descending a bit more through more pleasant woods. The treadway got easier rather quickly.

The trail ended up in a very narrow swath of land between houses on Concord Way, and Victory Lane all the way out to Stilson Hill Road and Sherman Road. The trail turned right on Rt 37, Sherman Road, for just a bit, and then crossed at Candlewood Mountain Road to head directly up into the woods. It was here it began to climb Pine Knob. We got our group shot on a giant multi leader hemlock tree near the base of the hill.
There were two ladies who had just finished hiking and were getting back into their car when we walked down. They seemed kind of shocked to see anyone else going in.

We climbed up and there was a bit of an opening with a view. The trail then went to the east a bit and got somewhat closer to some homes than I was expecting it to. It even got really close to a very clear and easy looking woods road, but never got on it. 

It just stayed out along the edge, and then dipped down through more rugged terrain to the east.

We started climbing for the last ascent to the top in this area ahead. While walking, my buddy Tom at work called me to talk to me about an altercation with employees and to discuss what we should do about it. I managed to talk with him almost the entire time of the worst part of the ascent, but when we reached the very top, I realized I had made a wrong turn.

The Housatonic Range Trail turns to the right up a rocky mess known as The Corkscrew on Pine Knob. What we had followed was a bypass trail, and I did notice when there was another color painted on the lower part of the blazes. While everyone was waiting at the top, I decided I was going to go all the way back down and find the correct trail, and experience whatever The Corkscrew was.

I watched as I went back down, and when the color changed to the solid sky blue again, I knew I was on the Housatonic Range main trail again.

I watched to the west to see if I could see it, and sure enough I found it, although it was kind of obscure from a fallen tree.

There were tons of rock piles immediately. I had to climb over these things, and then came into an odd sort of cave. The trail then went in two directions. There was a steeper one that required more hand holding, and then one really rough reach to the left, and then another somewhat simpler one to the right that was up through a hole among the rocks. I first tried to pull myself up the one to the left, but it wasn’t happening.

While doing water system work for my job, I had felt a pop in my hand, and had found that all of the muscles in it were inflamed. I was on orders not to lift more than ten pounds, so this was kind of hard for me.

I went to the right up through the hole, at which point the trail shifted hard to the left, and went to another rock that I had to flop my stomach onto and pull myself up. It was a really cool little side trip I was glad I tool. The trail leveled off just ahead, and I joined the others.

Jim and Pam regretted not having gone on that route, so we all agreed to take a longer break to let them both head back down and climb the Corkscrew as well.

Once they came back, happy they went, we continued on the trail to the south.

We continued climbing a bit more along Candlewood Mountain, and eventually found where the Kelly Slide Trail went to the right. This side trail is a big longer, goes down the mountain to the east a bit, passes a view, and then goes back up to the main trail again. I offered to the group that they would not have to follow me if they chose not to, and only those of us who wished to go to Kelly Slide would do so.
Only Kirk, Jim, and I decided to do the Kelly Slide. The others I told to go up the trail a bit, and watch for the intersection where the side trail came back in, and wait for us there. I wrongly assumed that this location would be obvious.

Earlier, a guy went running up the mountain past us at a pretty good speed, and as we were going down the Kelly Slide Trail, he was passing us coming back. He made mention of some of it being sketchy or something.

When we went down as far as the trail was going to go, we turned right to skirt the land contour. Views opened up of the Housatonic River looking down stream, and of the hills to the east. We soon reached what was referred to as Kelly Slide itself.
This was a pretty dangerous spot. At some point, the slide referenced was probably land that had eroded away and created this rock slide free of all vegetation. This also provided a splendid view of the Housatonic River valley toward Sherman area.

Abandoned old trail segment

We had to go up the slop off of the trail for a bit to get across the slide. There was loose ground with evergreen needles and leaves, and if we were to slide going across that, which would be easy to do, we’d be done for. I would suspect the Kelly Slide will grow more with visitation to the site for certain.

We took a short break to take in the view, then continued to the south and back up to the main trail. The climb there was really nasty, and there is apparently a current trail and abandoned old trail. Neither were well marked, and we ended up definitely on the old one going over serious rocks until we reached the obscure junction with the Housatonic Range Trail.

None of the rest of the group was there. We assumed they missed it and went ahead.

We reached the crest of the Candlewood Mountain, and the group was there waiting for us near to the top. The trail continued in more sparse woods, with some flat open rock, made a hard right turn, and reached the very top of the mountain where there was a stone pile. This was the southern terminus of the Housatonic Range Trail, a dead end.

This historic mountain top is so named because it was where Native Americans taught early settlers to make candles from pine pitch as a substitute for unavailable wax. It is said much of the Housatonic Range Trail were early native paths.

While everyone else took a break, I went over the aerial image maps of where to go next.
There was a woods road just to the west of the top of the mountain, so we wandered over to that and started following it to the south a bit. When I realized it was getting away from where I knew the trail was supposed to go, we turned left off trail through the woods.

It wasn’t really bad bushwhacking. Mostly sparse understory. We continued down into a saddle in the mountain, then had to climb steeply again straight ahead.

I was feeling pretty tired from all of the climbing that I had not been expecting at this point, but I led the way and grunted my way up to the top of this next bit, beyond which it was pretty easy.

There was more sparse undergrowth, but we were approaching a southern peak of Candlewood Mountain.
My goal here was to reach a spot shown on Google maps as Lookout Point. It was a high point with a steep cliff to the right that was once part of Housatonic Range Trail.
We crossed over an old woods road of sorts, which crossed over the mountain east to west, and then continued along to a couple of nice views through the trees to the left. This was what Google maps noted as the Lookout Point. Just then, I found a worn in trail that was overgrown and mossed over, as well as one remaining blue blaze on a tree. We’d certainly found the old trail route.

I didn’t know where the trail used to end, but I assume it went to what was pointed on the maps as Candlewood Lookout Tower. I can’t find any information on this tower or if it still exists at all.

Candlewood Lake made some sort of history as the first lake to ever be dammed for water storage as I understand. It is the largest body of water in Connecticut, and has a lot of recreation around it. This was actually the first time I had ever seen it on one of my hikes. Jillane and I took a walk along it once several years ago, but I never incorporated it into anything until this time.
We had a bit of a view of one of the beaches at the lake, and good views of the hills beyond.

We did not continue from the Lookout Point. The route to the south was going to take a long while, and we needed to get back down to begin on our way back loop, or so I thought.

Later on, I discovered about where the old trail used to go. It didn't go all the way to one of the points near Candlewood Lake or where google maps said the tower Was. 

It actually only went down the escarpment ahead of where we were, and then turned to the left along the Rocky River. It apparently crossed twice and followed the Rocky River out to the Housatonic River, or close to that anyway, and ended according to the old maps. 

I decided that the woods road we had seen earlier might be the best choice for part of the way down.
We continued on the way we came, and I think we found more of the trail that we hadn’t on the way up, but then turned off of it to the right a bit. I didn’t want to hit the woods road at the same spot we did before if we could cut a bit of a corner.

We passed through some interesting rock formations, over fallen trees, and eventually reached the woods road. It was not really used at all in the first bit, but then looked like it was used by ATVs. We followed the route, and at one point the ATV route deviated from the old road route, but it eventually took us on through to a high point on more improved quarry road or something.

Google maps shows a NE Utilities Access Road, but it did not follow any of what we were on until we were nearly at the bottom of Candlewood Mountain.
The wider road did some switchbacks, turned around a corner, and reached some steep vertical quarry walls. There was a clearing to the right with another view of Candlewood Lake. We could see speed boats moving and their wakes very prominently from this south facing view.

We passed some quarry walls and views, got back into the woods, and made another switchback to the right, which then took us along another level of quarry.
Based on the amount of weeds growing through this, nothing had been quarried at all in quite a long time.

We passed through one more open area, and then made the final descent to a wide open area at the base of the quarry. There was one big concrete abutment type of thing, probably for major loading purposes. 

The road was obviously used somewhat recently. I think I heard or read somewhere that these former quarries were going to become some sort of a housing development, but I’m not sure and haven’t read into it any further yet (or I tried googling it and found nothing).
Based on the old maps, when we reached the lower level of the quarry and started walking back out to the road, we were back on the former route of the Housatonic Range Trail. It ended about where the quarry access is today.

The road took us around a corner and out to Route 7, Kent Road.

I was really thirsty. Possibly the worst I’ve been in years. I brought extra water with me, but was not anticipating just how difficult the section of the Housatonic Range was going to be. I could have brought more, but I figured just after the halfway point we would be passing some civilization, and I would refill.
When we got to Route 7, Kent Road, I figured we would walk a very short distance to a hotel to the right, and then get more water there.

We did just that, reached the highway, turned right, and the hotel was closed. I was a bit concerned at this point. I had no water.

I figured we would pass something, and so we turned back to the north on Rt 7. If it got to be really bad, I’d just ask someone at their home if they minded if I used their hose or something.
We passed by a business to the right and walked through the lawn, utilizing whatever shade we could, and then reached Robert’s Garage. As we walked through the front lot parallel with the road, I saw a guy and asked if I could use their hose for some water. The guy didn’t speak any English, but he motioned to someone else who was some kind of boss.

He was friendly as could be, and escorted me to the back of the building where there was a restroom and deep sink for filling my bottles. I drank a generous amount before I even left the place, and had a full bottle when we left.
This water was outstanding. It tasted as good as Poland Spring or Deer Park for sure. I thanked them and we moved on up the road.

After a little bit of time, we reached the intersection with Boardman Road, where we turned right over the bridge across the Housatonic River. Right next to it was the closed original Boardman Bridge.

The Old Boardman Bridge is a rare example of a lenticular truss structure, built in 1887-88 across the Housatonic River. It was open to vehicular traffic until 1984, and then closed even to pedestrian traffic in 1985 because the decking was deemed too dangerous.

There are only three bridges like it in Connecticut, and funds have been put aside to repair it in the past, but they went to the nearby Lover’s Leap Bridge (which will be part of a future hike as well), and this one remained closed. Talks happened in July 2017 to figure out how to rehabilitate and open the bridge to pedestrians because there are small parks on both sides, and there is apparently a trail on the other side, as well as a future trail going in which will make the crossing more important.
We had been to the Old Boardman Bridge on a past hike before, and I did a couple of then and now compilations of it. I am enamored by the style of, so unique.

We have only passed a few of them in the history of our hikes. One was the Neshanic Station Bridge in New Jersey. Another was the Waterville Bridge on the Appalachian Trail in Swatara Gap. They’re just not very common.

The word Housatonic means “beyond the mountain” in native language, which is very appropriate when walking the section we had ahead of us.

I had decided to do this hike for a few reasons, but the main reason was probably because the latter portion of the hike would provide us with swimming opportunities along the Housatonic River.

The other reasons were obviously because I had not come back to this series in so long, and the last was because it sort of fits into a series loop between Appalachian Trail and Empire State Trail in New York.
I had recently finished all of the Maybrook Line on the Empire State Trail save for the segment between Brewster and Danbury. 

The different trails in the Housatonic Range to the south of this point would lead to another railroad bed that went directly into Danbury. The route we followed on the Appalachian Trail and to Housatonic Range would sort of close as a full loop. I just kind of like the idea.

When I went over Google maps just randomly looking at the area and discovered Sega Meadows, I was blown away. This looked like a beautiful, easy trail along the river, and the entire section from Boardman Bridge back to Gaylordsville looked like a fantastic hike.

Once across the river, we crossed the tracks of the Housatonic Railroad, and then headed up slightly. There was parking on the left for Sega Meadows, and a gate.

The route apparently used to be a road all the way through at one point. It took us just up hill from the tracks, then crossed them at grade and descended to the river edge.
There were some beautiful giant trees; sycamores, pines, and then we skirted a wide meadow along the left side.

Pretty soon, there was a great little path down to the left and a deep looking spot into the Housatonic. I think almost all of us went in for a dip, and it was just a really nice time. I was really glad to have made three new friends who were totally on board with what we were doing, and all had enough in common to appreciate something like a dip on a hot day in a beautiful river.

The water wasn’t really even too cold. It was just perfect, and the view of Boardman Mountain beyond was really nice.

We continued on the path out through the middle of the meadow for a bit, and then into another area of trees. We came up on a foot path that came in from the left, and then another exited to the left. We must have missed a good foot path section here, but we weren’t going to miss the next one.
The path went down a section of really nice wooden stairs right to the edge of the river. There was a nice little sing hung in the edge of a Sycamore tree, and a pleasant sandy shore to the river.

The trail stayed pretty close to the river and went over some undulating terrain as it headed north. There were also other side trails going different ways. At one point, we ended up on one that was closer to the river that got a bit more grown in as we moved ahead. Some of these were probably just social trails, not official routes, from having so many visitors. We remained along that trail, which went much higher up onto the slopes above the river for a good while, and eventually came out to the parking lot for Sega Meadows.

From this point, the river greenway just turns left and follows River Road to the north.
This beautiful section of road is unpaved and just follows along the river closely.

We were all together at first, but then Jim, Pam, and Mary went ahead of us. We could see them around corners for a bit, but then they got to moving farther ahead and we ended up not seeing them again for the rest of the hike.

We were most of the time sandwiched pretty tightly between the Housatonic Railroad and the river. We passed one spot where a pipe was placed next to an old box culvert, which means it probably floods pretty badly here.

While we were walking this narrow road section, not all that many cars went by, but one pulled over to chat with us.

I never know what to expect with people, but this guy was a trip. I had handed Kirk my beer, and he tried to hide it kind of behind him since this guy was so close, but he clearly wasn’t concerned about anything. He was switching between putting I think a cigar in his mouth followed by a marijuana vape or something. I recall Kirk thought it was particularly funny.
He asked if we smoke or anything, and I took my beer back, swigged it, and said this was what I went with. It was one of the strong ones, I think a bottle of Weyerbacher Insanity from the latest batch. I offered him some, but he declined saying that he didn’t drink.

Out of the blue, the guy asked if we were Germans, and myself and Diane definitely have German last names. It was just an oddball exchange, and I wondered if this guy was one of the Schaghticoke tribe members.

The Schaghticoke Reservation is the only native American reservation the Appalachian Trail passes through, in western Connecticut. From what I’ve seen with them online, they can be some funny characters, and come across as very friendly like this one. There was one particular site was schaghticoke.net which claims not to be affiliated with the tribe. I’m not sure if the page owner is a member of the tribe, or just an eccentric person, but I absolutely loved it and found some great information on area trails there including the old trail map.

We were thoroughly amused by the character we’d met, and continued walking the road to the north some more. It moved away from the river a bit more after a couple more views, and then passed through dense woods with tons of multiflora rose along the sides.

As we started to approach the southern end of Gaylordsville, there was an enormous Sycamore on the left.

We passed by a farm and some residences, over a creek, and then further into town.

To the left, there was an oddball five tier house to the left side of the road. I didn’t know what practical use it used to be, or is, and didn’t think much on it right away.

Upon doing a little bit of research, I found that this was known as “The Spite House”, and it had quite an amazing story. Despite being a fan of Weird NJ/Weird US, I had never really heard of a Spite House before, but apparently it is a thing.
A Spite House is one constructed or modified in such a way as to intentionally irritate neighbors or other parties with land stakes. They are usually obstructive or flamboyant, and can be strange and impractical. This one is sometimes referred to as the "Cake House".
This particular house was built as "a monument to injustice" by Jan Pol, a man who adopted a young girl and had her taken away by the state because proper formal paperwork had not been done. There is also a story that the girl became pregnant, and was taken away when it was assumed the baby had been fathered by Pol.

And so, Pol constructed what was considered to be an eyesore in an otherwise charming and historic little village.

To the right, we had the Old Oak Tavern. This would be our late lunch/dinner stop.

This stop would tie directly in to the history of Gaylordsville itself.
The building was constructed as post office and general store by Reverend Peter Gaylord in 1805. 

Of course, communities grow around convenience and commerce. It was just on the east side of the bridge spanning the river.
Inside, original hand hewn timbers can still be seen.
The bar and restaurant takes it's name from the old Oak tree General George Washington met with his troops in 1789. Sadly, the tree fell several years ago; we walked by the site of the tree on the previous Housatonic Range hike several years ago. It’s always nice to at least have an understanding of the references in these places, because I knew exactly what the history referred to when reading it.

I suspect the first covered bridge over the Housatonic was built around the time of the store, but the second was constructed in 1876 to replace the original that was washed out.

The bridge was bypassed by a new structure of through truss design upstream, and the two coexisted for a time until whatever happened when the covered bridge was lost. There are still abutments remaining to the bridge, as well as a small pile of stones where the pier was in the middle of the river. The through truss bridge was replaced only in recent years with the current Rt 7 bridge that stands today.

We had a very nice meal, and I think I went all out on something more expensive but delicious. I forget what it was. I also had Backeast Brewery Citra Double Scoop IPA which was pretty good, to go with it.

When the three of us were done, we headed out and walked across the bridge where we could see the remnants of the original bridge.

We continued from there along Rt 7 to the south again, and it wasn’t too far to the diner where we parked. 

The other three had stopped for lunch at an Italian restaurant just before we got back, which was why we had not seen them. I’m sure it was good, but I was glad we went for the historic place.

The old Methodist Church was on the way back, built in 1826, and was one of those nice high steeple structures.

There was also a really beautiful Sycamore along the way as we continued back toward the lot.

It had really be a great day full of all sorts of interesting things. I was so glad to have done this section, and I really wish I lived closer to this so I could continue more easily with the series. We have great stuff where I live, but everywhere has its own charms. I love where I live, but visiting places as cool as this is certainly great.