Caldwell Woods

Caldwell is a lovely slice of the Cook County forest preserve. The Chicago river cuts through the woods and there are usually ducks hanging out by the bridge waiting for the kids to feed them.
It’s an easy access point to the north branch trail. So between that and the picnic area, the parking lot gets full quickly. There’s street parking as a backup plan.
And best of all, Super Dawg is closeby. Hello, Whoopskidawg.

one of my favorate hang outs its a way to unwind after a long day at work. also for a day off of work you can have much fun grilling, ball playing, and what ever kind of entertanment you can think up of.

Did you know they have a warming center for people sledding on a nearby hill in the winter? Do you even know what a warming center is?! Yeah me either and that’s only the half of it. Go and find the fuck out.

I am from out of town, first time I did this trail. Enjoyed it. I started at Caldwell Woods and went all the way up through the Botanical Gardens (~ 30 miles roundtrip). It’s well marked, solid asphalt [no cracks that I saw!] and a bonus is that if you have a hybrid or mountain bike there are «some» crushed limestone/​hard packed routes that parallel the asphalt trail which provide for a nice break — it’s not mountain biking but it’s still a nice diversion from the asphalt trail if you like some trail riding.
One thing that did disappoint, if you are looking for any civility from other riders — might want to go elsewhere. I do not need to know your life story, no need to say «hello» or acknowledge another human being with a pulse enjoying the outdoors like you with a head nod or «good morning», but there’s something called trail etiquette where you call at least call out «pass» etc. Apparently, there are such advanced riders on this course, they do not need to have any etiquette. It doesn’t cost extra to be nice people.

This is a great place to walk, bike, or have a bbq. If you take the bike trail make sure you pay attention to the trail map or you could end up biking all the way to Lake Cook road!

If you get here blindfolded the whole time, you wouldn’t think you were in Chicago. Thank god they didn’t cut down anymore of the wilderness, back when the city was in its early stages, because the forest preserve area is huge, especially by city standards. Plenty of parking, not too crowded, and surprisingly, there were a good amount of deer in the area. Plus, its a well kept area, no gangbangers around.

awesome forest. big. big freakin deer! It’s like texas. Everything’s bigger.
There a million entrances, exists, etc. The thing is so huge that it goes from mid-​chicago all the way up to lake cook road… so like 30 miles or more? Quite big considering the urban environment.

This place is fantastic, any time of the year, during the summer, we would take long bike rides all the way up to Niles and beyond with our young daughter in tow.
There are also kid parks, places to have awesome picnics and super cool trails through the woods. In the fall, we would go often to enjoy the foliage, and the winters we can cross country ski through the trails. We were fortunate to live right in front and there is nothing like the early morning smell of woods and the sight of the dew at the crack of dawn.
This is one of those places that makes all the seasons worth living through them.

We stopped here today because Christopher and I are Geocachers and we have maintained a cache in the woods here since 2002 and it was time to check it out and see that all was well. If you have a GPS, Geocaching and Unilocaling go really well together. We use Unilocal to pick a dining destination and then combine it with some good old caching. Caches are peppered all over so it is easy to find one or two to pair up with your Unilocal destinations. Makes for an eventful day.
Caldwell Woods is a really nice place. It has something for almost every interest. I am not so much about the recreational parts as the nature. Over the years I have loved to follow the development of the Bunker Hill Prairie. I used to come here quite often with a photographer friend of mine and spend hours taking pics of the prairie plants and insects. Even though the woodlands in our forest preserve system are damaged, it is still nice to spend time here.

A great place to bike or picnic on the weekends. Lots of families and friends hanging out here on warm summer days. Plenty of room for frisbee and volleyball, too.

Great big hills for sledding? Check. Winding paths for disappearing into the woods? Check. River full of ducks? Check. Deer everywhere at night? Check. Nice path or bikers/​bladers? Check.
Yeah, this place isn’t missing anything. Pretty clean and well kept. There are some really beautiful green patches in the woods, some nice picnic areas, and a couple good spots to sneak off with your girlfriend and get lost in the brush.
If you drop by here in the summer you’re bound to stumble upon a picnic full of friendly people offering you a burger, or later, high school students who’ve rolled in keg into one of the clearing, offering you a big red dixie cup. If you show up in the fall, make sure to take some time and enjoy the «Haunted Trails». Maybe not the scariest thing on earth, but even as an adult, it’s still fun.

This is the location of a lot of year-​round greatness. In the summer time you can enjoy the Whealan Pool aquatic center. The pool is zero-​depth which is nice for younger kids. They also have a pretty cool water play thingamabob with short slides and whatnot. Also, there’s a lap swimming area and two water slides. It’s a good place to take a picnic or to lay out in the sun on the chaise loungers they have everywhere. It’s a good place. I just called today and they should be opening some time in June and their hours are generally 1 – 8
Also, right next to the Jenson slides there’s a nice little area for sledding… or if you’re daring in the summer time you can go ice blocking. You can see my list for more info about ice blocking.
In addition, this area is the start of the North Branch Bike trail which is also a great place to ride-​you can go all the way to the botanic gardens!

UPDATE 12/31:They repaved! I dont know if they did the whole bike path or not, but at least by me there is all new asphalt down. Cant wait for spring to try the rollerblades on it! Yay!
The beginning of the bike trail starts at the intersection of Devon and Central and ends at the Botanical Garden in Glencoe. Yep, you can ride that whole way if you want to be all hard-​core and nutter about it if ya want. Me, I get to about Dempster and I’ve had it for the day. This is a beautiful Forest Preserve, though. Lots of open fields, wilderness and deer to see if you are lucky. It’s tough to rollerblade on, though, since the asphalt is kinda bumpy and old.

A great place in the summertime and the wintertime. In the summer there’s picnics going on there all the time and you can always take a dip in Whealan pool to cool off. In the winter time you can sled next to the Jensen Slides. I’m not sure if they still do this, but they used to have a «Haunted Trails» Halloween haunted woods which was a ton of fun!

This huge woods/​forest preserve covers so much ground that part of it’s property is in Niles, Il as well. Many beautiful acres of land are here and the north branch of Chgo. River runs thru the middle of this land. On the premises is also Whealen Pool that is one of the best pools that is part of the Chgo. Park District. There is also a bike path as well that stretches for well over a mile thru the forest preserve.