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Berkshire Private Tours
Cranwell Golf Course
Indian Summer Tours
Killington Summit
New England Adventure Tours
Kayaking in New England
New England Autumn
Pumpkin Picking
New England Tours
Indian Summer Views
New England Historic Home
Fall Foliage Tours
Fall Foliage
Norman Rockwell Museum
Mountain Biking
Shaker Boxes
Cranwell Resort


Greylock Discovery Tours is proud to offer private, customized tour and outing programs for clients who desire a higher level of service and attention.  Designing, organizing and booking guided and unguided programs throughout New England and the Middle Atlantic States has been a specialty of our company for many years.

 Let us do the planning and organizing for your family retreat or friends getaway weekend, so you can have fun and not worry about the details.  We’re experts on the destinations we visit and can plan a program for 2 persons or 100 persons.  Everything will be organized including your accommodations, meals, transportation and sightseeing.  We provide maps, guidebooks and recommendations on your customized and personalized itinerary.

Private Tours are a great way to reconnect with old friends whose lives have gotten too busy to spend quality time together.

“I invited college friends that I hadn't seen in years to come along, and boy, did we have fun!” 

Judi Powell, Private Client, Montana

Berkshire Private Outings

Berkshire Tours
Berkshire Snowshoeing

Spend a few hours or the whole day with a local expert exploring the Berkshires natural history and cultural attractions.  We offer hikes, canoe and kayak trips, sightseeing excursions and historical tours from one to twenty persons.  See the area with someone who can guide you and add value to your visit.


Naturalist Guided Hike: Come see nature’s beauty in verdant Tyringham Valley.  Guests will hike along the historic Appalachian Trail through meadows and forest viewing classic New England scenery.  Hiking boots or sturdy walking shoes recommended.  Degree of Difficulty: easy to moderate.  Transportation and light snack included. 


Housatonic River Canoe Trip:  This 6-mile, flat-water, canoe trip takes about 2 hours, and wanders through one of the most scenic and wild areas of Lenox.  Exalt as your naturalist guide interprets the fauna and flora that make the river habitat their home.  Degree of Difficulty:  easy.  Transportation and light snack included.


Berkshire Cottages and Historical Tour:  Learn how and why artists, writers, musicians and others have flocked to the Berkshires over the last 150 years to make this area “Americas Premier Cultural Resort.”  Often called, the “inland Newport” due to the numerous “cottages” built during the “Gilded Age”, the Berkshires radiates with culture and history.  A walking tour of the Tanglewood campus, Village of Stockbridge and Chesterwood – home of Daniel Chester French – sculptor of Abraham Lincoln in the Lincoln Memorial – are included.  Three and half hours.  Transportation included.


Summit Chairlift Ride:  Take the easy way to the summit on the high-speed six-person chairlift at the Jiminy Peak Resort in Hancock, MA.  View the beautiful colors of autumn spreading across the valleys and mountaintops of the Taconic and Hoosac Mountain Ranges.  A short, naturalist guided walk along the mountain ridge will offer different views in all directions.  Refreshments will be served at the mountaintop lodge while you bask in the glow of autumn light.  Transportation included.


Landscape Photography:  Here’s a chance to bring home that classic New England fall foliage photograph.  Join award winning Berkshire photographer, Jamey Schumacher as he leads you to those special places where the light and colors are just right for that once-in-a-great-while snapshot.  Transportation included.


Two Great Museums – Part One:  The Sterling and Francine Clark Art Museum is world renowned for its collection of impressionist paintings – over 70 Renoirs alone!  Join the museum’s staff as they take you on a tour of what Berkshirites consider “our little jewel” in the woods.  The Clark also has fine collections of silver and early American paintings from the Hudson River School.  Then, it’s off to the Massachusetts Museum of Contemporary Art (MassMoCA).  This unique museum will eventually be the world’s largest museum dedicated to contemporary art.  Founded in 1997, the museum is located in a turn-of-the-century mill complex comprising 28 buildings.  Gargantuan sized galleries allow the public to view works of art rarely seen because of their size.  A very unique experience.  Transportation and admission included.


Two Great Museums – Part Two:  Norman Rockwell is without doubt, America’s favorite illustrator.  See the “Four Freedoms”, New York Post cover collection and many other well-known paintings that offer a snapshot of America during the 1940s, 50s and 60s.  Afterwards, we journey just down the road to the home and studio of Daniel Chester French – our country’s premier turn-of-the-century sculptor.  Mr. French is best known as the sculptor of Abraham Lincoln in the Memorial in Washington, D.C.   Transportation included.


Backcountry Bike Riding:  Enjoy a stimulating bike ride in the refreshing, cool autumn air.  Backcountry roads take you along scenic byways and through quintessential New England villages, stopping to explore various historic or cultural sites.  Transportation, bikes, helmets and lunch included.


Berkshire Antiquing:  Join antique expert Charles Flint on a fun-filled antiquing tour of the Berkshires.  Charlie will entertain and educate as the group travels from shop to shop seeking out those rare and…well, not so rare finds.  There are well over 100 antique shops in the Berkshires and Charlie will bring you to the best of the best.  Transportation and light snack included.


Pontoon Boat Trip:  Spend the afternoon cruising Onota Lake against the majestic backdrop of the Taconic Range.  The lake provides one of the best views of the Berkshires.  Transportation and light refreshments included.


Fly Fishing:  Local fishing guides take small groups of 2-3 persons to their favorite fishing haunts.  Instruction provided for beginners and novices.  Whether river, lake or stream, you are sure to enjoy a pleasant day outdoors near the water.  Transportation and lunch included.


Kayaking Adventure:  Enjoy the quiet and solitude of kayaking on scenic Goose and Upper Goose Ponds.  Naturalist guides offer instruction for all levels of accomplishment.  Transportation included.


Theater, Dance and Music Festivals:  The Berkshires is alive with the Tanglewood Music, Jacob’s Pillow Dance and a multitude of theater festivals from May through October.  Enjoy a theater performance by Shakespeare & Co. or music under the stars at Tanglewood.  Pre- and post performance events including dinner or desert parties can be arranged as well.


Hancock Shaker Village Dining:  Enjoy a special evening at Hancock Shaker Village with a delicious candlelit dinner in the meetinghouse.  Experience life as the Shakers did well over a century ago.


Portrait Photography:  Master photographer Edward Acker captures couples, individuals and group “personalities” in black and white portrait photography and spontaneous snapshots.   He has worked with President and Mrs. Clinton on Martha’s Vineyard, Arnold Palmer, Arthur Blank and Bernie Marcus (Home Depot), Madonna and many other corporations, organizations and personalities.


Berkshire Ballooning:  Rise and shine to meet the day in this early morning take-off.  What better way to see the beautiful fall foliage along mountain ridges and fertile valleys.  Transportation included.


Dried Flower Arranging:  Learn the art of collecting, preserving and arranging dried flowers.


Dine Around History:   Your group is divided into smaller groups to dine around in Berkshire History.  Imagine yourself dining in a Shaker Meeting House by candlelight as the Shakers did over a century ago, or contemplating Moby Dick where Herman Melville’s once dined.  A fun, fact filled evening of food and history.

New England and
Mid-Atlantic States
Private Tours

Mid-Atlantic Tours
Cape May Marina

Greylock Discovery Tours has planned and operated many customized self guiding tours throughout the Middle Atlantic States for couples and friends traveling together. Call us to help you plan an itinerary.

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