Windham County Complete

My pick for best waterfall in the county (even if it is man-made)

I don’t think I’ve taken enough time to sit back and digest what seems to be a pretty big milestone in the development of this site. Partly because I’ve been pushing against a self imposed deadline of the end of November, partly because this has been in some sense five years in the making, and partly because it seems like the work has only just begun. So really I’m just going to sit down, write, and see what comes out.

Windham County is 521 squares miles across 15 towns often referred to as the ‘Quiet Corner’ of Connecticut. Throughout my explorations I’ve added 107 locations to the map but because a location can have multiple recreational uses and multi-town trails might not get multiple listings on the site there are closer to 125 different hikes, 26 boating/fishing spots, 10 mountain bike areas, 7 overlooks, 7 waterfalls/cascades, 5 disc golf courses, 3 backpacking spots, two river trails, and 2 rock climbing/bouldering spots.

Now by saying ‘Windham County complete’ I am not claiming I’ve hiked every mile of every trail at every location. Perfection is the enemy of progress, and the progress made so far is reason to celebrate. I still haven’t paddled the length of the Quinebaug River, fished all the ponds, or mountain biked all the loops. I have, however, gotten the locations onto the map and updated all the guides to make it easy to find the ways that you want to explore the county. When I said in the opener that it seems like the work has only just begun I mean that the goal is to be a complete guide to all your Connecticut outdoor activities. Thus, there is still so much to be learned and shared about each and every location now present on the map.

I’ve been hiking in Windham County almost my entire life. A tag line I use on social media is ‘making a map to understand the territory’ because the entire process of this site has been, the more you dig the more you find. Before this site there were dozens of trails that I had driven past countless times and never even knew they were there. Now I can take a drive and point out a nearby hike in any direction.

Before this site there were spots in parks that despite having hiked or run so many times I’d never taken that unblazed side trail which lead to some secret view or some abandoned brick building. Or now I’ll read some seemingly unrelated article or newspaper clipping and discover some new bit of interest relating to some hiking location about the person who blazed the trail or why a feature is named. I’d never have learned about the Quinebaug Highlands, the native american word for important fishing place, or how much a ravine trail can change in just a few short years.

From back in 2016, one of my first years really exploring Windham County

I think that’s the biggest takeaway from this effort so far. Had I not taken the plunge to really get to know the area in this way I would never have known about all these places and experiences. And in turn, it nows sits as a kind of living document for anyone else looking for a way to explore Windham County and increasingly the rest of the state.

All that said, just for fun I’ve purposefully left two locations off the map, small spots without much weight, just in case anyone wants to nerd out, check my work, and try to spot them. And if I’ve somehow missed some great location altogether shoot me a message with the details and I’ll send you a ExploreCT t-shirt as a reward.

Either way I hope you’ll take some time to peruse what the northeast part of the state has to offer and as always I welcome any notes and feedback about ways the guides could be more useful to you. An idea for my next round of edits is a progression – as in here’s 1-2 great but easiest hikes, here’s 1-2 moderate hikes, and these are the two most challenging hikes in the county. Another is a curated day or weekend worth of exploring. Always a work in progress! And if you’re reading this at some point in the future, maybe it’s already there.

There is still much to explore and experience and connect in the Quiet Corner. History to uncover, trail connections to make, hidden gems to find. For now, Windham County is complete, right up until I hit publish 😉