Since more and more people I run into are interested in hearing about the various day hiking opportunities in the Stamford/Norwalk area, I figured I’d save myself some time and just write it down once. So here’s a quick list of local hiking spots and my opinion of each. For the record, you should make your own judgments as to difficulty and what you can handle; my opinion might differ radically from yours. Make sure you are prepared for the hike you are doing.
Mianus River Park – Stamford, CT – Great hiking, very easy trails, very close. Makes a good spot to go if you just want to get outside for a bit. Only major downside is that it isn’t that large and is very heavily trafficked.
Babcock Preserve – Greenwich, CT – Only been there once so far and it was a nice enough place. Very small though; the largest loop you can do is just over 3 miles. Depending on how sensitive your hearing is, you may be able to hear traffic noise throughout. Some of the trails are very well marked, but you’ll need to pay attention on the Red Trail. Some of the blazes are missing and the trail gets confusing a points. Not too bad.
Devil’s Den Nature Preserve – Weston, CT – A the largest of the local preserves, Devil’s Den has several long loops you can do with lots of hiking space. Once you get away from the trail head, the trails are pretty much deserted. This is one of my favorite places to go hiking in the immediate area. One major problem though, the area is completely bug infested during the summer. I skip it during the summer months and go elsewhere instead.
Ward Pound Ridge County Park – Westchester County, NY – Despite not being in CT, Pound Ridge is within easy driving distance of Stamford. (1/2 hour easy) While not as hilly as Devil’s Den, Pound Ridge has lots of space and plenty of trails. All the trails I’ve been on were well marked and easy to navigate – almost too much so. Pound Ridge would also be a good place to trail run. Particularly on the colored trails which are wide and relatively flat. (I’ve been on Red, Green, Yellow, & Orange. Can’t say anything about the others, though I expect they’re similar.)
Harriman State Park – New York near 287 & 87 junction – A bit further away (1 hour by car), but if you want to get out into the wilderness and do some serious hiking (either day hikes or backpacking) this is the closest decent place I know of. I’ve done several hikes in Harriman and enjoyed each of them. Trail difficulty varies wildly so make sure you know what you’re getting yourself into.
One additional resource I’d point you to is Michael Brochstein’s list of day hikes near New York City. He has a lot of good hikes in there, many of which I’ve done myself. Only catch is that most of his hikes are a little further away. Also be warned, I find myself often disagreeing with his difficulty estimates, but not in any consistent way.
Another resource I just discovered covers many of the smaller nature areas in and around Westchester County. I haven’t hiked any of these yet so I really can’t say anything for the quality of the list