A Little Background...
I grew up in western Connecticut and lived in Massachusetts for about 12 years before returning to Connecticut. The bulk of hikes listed here are all the hikes I've ever been on...although recently Ryan Auge has started adding great hikes in the northwestern part of Massachusetts (I encourage anyone else to do the same.)
As the youngest in a "guys only" family, I was allowed to tag along a lot. A favorite memory was driving up Route 7 to escape suburbia with my eldest brothers. They had a genuine love of nature but they also had other reasons for getting away...like escaping "the old man and the old lady"! Crankin' rock n' roll in beat up cars, which used to be considered cool, and finding a good place to hang out was a high priority. It was on one of these roads trips with a brother and his friends that my love of hiking and overviews began.
The overview fixation started at Cobble Mt. in Macedonia State Park when I hiked up the crest of a hilltop and walked towards the overview that faces west. I don't know why the scene hit me the way it did, but it did. As my brother and friends found a spot to chill out and talked about who-knows-what, I became fixated with the views. Rolling hills seemed to go on forever and farmlands everywhere...it was a crystal clear day with a big blue sky and just a few dabs of clouds. The Catskills loomed large in the way-off distance which I would later learn was an extra treat because they're not always seen depending upon atmospheric conditions. I had never seen anything like that before and the thought that you climbed hard to escape everyday life and arrived in a different world had strong appeal. To this day, I still love the idea that you can hike long and hard for a nice reward.
Now, as some of you know, Cobble Mt. really isn't that big of a deal nor are the views going to rival the Rockies anytime soon (and it doesn't help that recent home construction has sort of ruined the farmland and pristine views for me...but it's still nice!) but Cobble made a huge impact on me and ever since then I've loved the idea of climbing up a hill/mountain to check out the views. The love stayed with me throughout my youth and waned a bit in my early 20's but I starting hiking again in my late 20's-early 30's. As the Internet became mainstream I decided to create a hiking page in order to contribute to the free sharing of information. Every time I went on a hike I'd take some photos, write about, and post it on the web. I got some nice feedback so in 2000 I bought the domain name berkshirehiking.com to provide a resource for those looking for outdoor fun. I love this region because you can hop in a car, drive off, and easily find a good trail within a half hour. You can hike into or up a trail and get lost for awhile...without having to make major plans or spend hours and hours on a marathon hike loaded down with backpacks and supplies. In southern New England you can explore without having to be in world class shape or trained in any outdoor techniques.
Though this area lacks the awe inspiring beauty of the American West, the rugged majesty of the Swiss Alps, or boreal wonder of Alaska, I've come to realize it produces boundless hidden treasures that are well within reach of anyone who wants to venture out. That's what makes this area unique and a world class spot for hiking. A great nature experience is accessible to all. The awesome beauty of the Taconic Plateau in the tri-state boundary area can remind me of Ireland's sweeping views over rolling farmland, Austin's hill country peaking down on the city, Vermont's deep, dark pine forests, and even Hawaii has come to mind as I've hiked alongside small waterfalls cascading down smooth rocks and blanketed by lush forests. Southern Connecticut is postcard New England and at times the hill trails feel more like Adirondack Mountain trails. Massachusetts' mountains have felt like Maine or the White Mountains of New Hampshire. Northampton/Amherst hiking gave me a sense of Europe in certain spots as the hill trails surrounding these college towns produce postcard views of the region's historical buildings and modern day hustle and bustle. The river valleys, lakes, ponds, streams, and resevoirs can't be counted and create a whole different hiking experience altogether.
I went through a phase years ago where I got down on the area because of all the development, loss of open space, lack of affordable housing (lack of "affordable expensive" housing too!), increased traffic, etc. But in building this site I was reminded of a good childhood and youth. I've used the trails of Connecticut and parts Massachusetts to "get away from it all" with older brothers when we were kids, train for high school basketball, make-out with girls, study college material in places that make libraries seem cacophonous, and to gain some much needed solitude and refreshment as an adult. Throughout all those phases, nature continued to impress me. I have an endless slide show in my mind of great views, blazing sunrises/sunsets, meteor showers, sparkling water experiences, wild animal encounters, along with numerous other scenes that I can't recall right now but always seem to flash across my mind's eye in an instant, putting a smile on my face.
98% of my hikes were flawless and wonderful but not all of them have been pretty or fun. Being cold and hungry and hours from the car isn't fun...mostly done when I was young and stupid. Nearly getting struck by lighting isn't fun either because you shouldn't hike in a forest with all those wooden lightning rods nor make a crazed dash for the car through a massive open field while lightning explodes directly overhead (just because you're moving really fast doesn't mean lighting still can't hit the tallest object in a field)...done when I was young and stupid. Staying up on mountain to watch a colorful sunset and then the stars emerge is cool but not when you're alone, shouldn't be hiking in the dark, and haven't told anyone where you'd be...then badly twisting your ankle on a rock because the flashlight you didn't bring as a backup option couldn't light the trail to reveal the large ankle twisting rock...done when I was young and stupid. Bringing a "hot chick" to a waterfall and then convincing her there's another trail to a mountain top that really isn't that far, only to have her nearly collapse from exhaustion and then say in an alarmingly terrifying voice "I don't think I can make it back!!"...done when I was young and stupid. Although they weren't fun experiences they can bring on bursts of laughter and have certainly made me wiser, and therefore a better hiker.
And my new found "with age comes wisdom" attitude should make this website a reliable source of information for you in order to find choice spots in this great region. I'll do my best to provide you with timely information and precise directions. There are major search engines and plenty of map sites, but they only take you so far. Berkshire Hiking is about locals writing about local places...to get you outside on a nice day and provide you with reliable information and perfect driving directions. I hope you enjoy the site and let me know if there is anything I can do to improve it. And if you're looking for a hiking guide or someone to help you plan an outing, please contact me. I'd love to help you find, or show you, all the hidden treasures I've come to know.
To inquire about Berkshire Hiking Tours please click here to send email or call 203.788.7665.