"In the woods is perpetual youth" - Emerson

Guided hikes: 1-2 hours north of NYC!


CT/MA Hikes | Appalachian Trail trips/lessons | Corporate/Youth Groups | Artists

Berkshire Hiking services

Berkshire Hiking is set up so that you can find your own trail to disappear into but there are times when a guided hike might be preferred. Berkshire Hiking offers private hiking tours for individuals, friends, family, schools, businesses. Litchfield Hills and Berkshire Mountains offer something for everyone and all abilities whether your interests involve Appalachian Trail backpacking or short beginner hikes. All levels and abilities accommodated with a prices that work within your budget.



The bulk of the guided hikes offered through Berkshire Hiking are in western Connecticut and Massachusetts. Danbury/Kent/Cornwall/Salisbury corridor of CT is where Berkshire Hiking primarily focuses on as well as Massachusetts's highest mountain (Mt. Greylock) and Mt. Washington State Forest (CT/MA/NY tri-state boundary) regions. Nearly 150 miles of Appalachian Trail rise up and down through western CT/MA near the New York border which makes it ideal to explore. However, we can pretty much book a hike anywhere (hmmm..."anywhere" is relative term... but like the old cowboy song once declared "if you got the money, honey...I got the time..") so if big mountains of Maine or New Hampshire interest you we can recommmend a friendly, highly trained, wilderness guide.

If you're looking to join a large open hike group your best bet is to join Appalachian Mountain Club local chapters: New York, Connecticut, Massachusetts, or Boston or visit a local chapter of Audubon, or any nature center near you. They have a lot of activities to choose from and welcome individuals to join in with their group. They're extremely knowledgeable, reputable, and organized.

Boston residents and visitors: Berkshire County is a western MA outdoor paradise. Mount Greylock and the surrounding mountains are as good as it gets in the Berkshires. Wonderful, wonderful place that at times feels more like Alaska. Price range is $50 to $250 and that price is the same whether it's one or or a dozen people. The longer and harder the hike, the more expensive so beginner/intermediate hikes are reasonably priced and the guides are extremely knowledgeable. Email  203.788.7665

New York City residents and visitors: Hop on Metro North train out of Grand Central Station and 2 hours later you'll be on trail in Kent, CT a world away from NYC. Or take a ride in the car and meet the guide at the trail and your scenic trip will be just as nice as the hike itself. Short, medium, and long hikes are avavailable. Price range is $50 to $225 and that price is the same where it's one or ten people. Most of the hikes are in Kent or Cornwall, CT but higher mountains and other CT destinations are available so inquire. It's an underrated hiking destination and a beautiful region. It's a one-and-a-half hour train ride from Grand Central Station in Manhattan to Pawling, NY which is right near hiking destinations in Kent, CT. You'll be picked up at local train station, driven to nice nature spot, and back again to your train. You can plan out a nice day and be back in time for a late NYC dinner (which in NYC I suppose would just be normal dining hours!. Email  203.788.7665

Group outings (youth groups, schools, companies, etc.): Please contact us to get ideas and pricing. We can plan hikes to relax and enjoy but we also have a certified hiking guide experienced with combining hikes with leadership/communication games and lessons. The guide for group outings is highly trained and certified to handle any type of outing. Email  203.788.7665

Backpacking/camping lessons
Ever wonder how to properly pack and unpack a campground? Cook a meal out on the trail? Berkshire Hiking has a certified instructor in all things outdoors and available for private lessons for individuals or larger groups.
Email  203.788.7665

Team Leadership
Send out a group of friends, co-workers, young people, teammates on a hike where simple, fun, useless workshops are conducted along the way. The outing can be as casual or extensive as you'd like it to be. It can be something that really pushes the group to work and communicate together or something really mellow designed to teach a few basic communication techniques and group tasks
Email  203.788.7665

Artist's Inspiration
If you are an artist (amateur or professional) and looking to nature for inspiration, hire a Berkshire Hiking guide to lead you to magnificent places. Whether it's for a few hours, a day, or even weekend, Berkshire Hiking can be your personal tour guide and driver. We'll hike in with you to show you the more remote places or drop you off at a spot you've noticed along the way. We'll keep your supplies fresh, your stomach full, and be a personal assistant and local information guide.
Email or call for more information: Email  203.788.7665

A Berkshire Hiking guide can meet you at the trail head, or at a local establishment (gas station, restaurant, etc.) for a convenient rendezvous. If you're in the area without transportation we may be able to make pickups and drop offs.

Metro North's hiking getaways

Bus and Train info
1) At this time there aren't any bus lines that run through the heart of Litchfield Hills and Berkshire Mountains but you can search major bus lines for updates or routes that run nearby.
2) Metro North train that runs out of Grand Central Station in Manhattan and goes upstate New York has an Appalachian Trail stop which will drop you off right at the trail head near the Connecticut border. Check their website for information, Metro North getaway , and click on MAPS from the top menu and then Metro-North Rail for a visual of their stations. ). Metro North also wants it known they are pro hiking! They've created a page to help those looking to escape the city for some hiking. Outbound getaway . Berkshire Hiking as of now can pick you up along the Harlem Valley line such as the Appalachian Trail stop, but the Hudson line has some great stop offs (A.T., Harriman Park and Bear Mountain).

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