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Theatre and Music Tours
Tanglewood Music Festival

Heritage Tours

Performing Arts

Cultural Tours

Specialty Tours

New England Cultural Art Tours
Andrew DeVries Sculpture
Natural History Tours
Wildlife Presentation
Food Tours
Fine Dining
Theater and Music Tours
Jacob's Pillow
Dance Festival
Theater and Music Tours
Yo-Yo Ma, Cellist
New England Museums
Home of Herman Melville
New England Fall Foliage
Fall Foliage
New England Historic Home
New England Historic Home
Edith Wharton's
The Mount
New England Winter Tours
Horse Drawn Sleigh Ride
Theater and Music Tours
Shakespeare & Co.


Greylock Discovery Tours has been creating, organizing, and operating tours for seniors and adults since 1989.   Our emphasis has always been serving tour operators and travel agents by developing tour products that keep their customers coming back for more.   We pride ourselves on finding the right formula for every tour group, from the budget minded to groups that demand the best of everything.   Our aim is to deliver great tours and service in all price categories.


Below are some brief descriptions of themed tours we have operated in a variety of destinations.  Themed trips are meant to stimulate ideas for your group touring needs.  Each tour is customized and can be combined in various ways.  We are flexible in putting the right tour together just for you.  Any combination of the following themes is possible.  We would be pleased to send you a full itinerary for any tour upon request.  Give us a call and let’s work together to offer your clients the best tour possible. 



New England Cultural Art Tours


Historic Homes and Gardens

This two, three or four night program visits New England historic homes and gardens.  A sampling includes Roosevelt’s New Hyde Park Estate, Edith Wharton’s - The Mount, Joseph Choate’s Naumkeag, Daniel Chester French’s Chesterwood and Robert Todd Lincoln’s Hildene.

Massachusetts Living History Museums

Explore three living history museums depicting 18th, 19th and 20th century life in New England.  Our first stop is Plimoth Plantation to learn about the lives of the earliest settlers arriving in the new world, and the Native Americans they befriended.  Moving right along to the next century, we spend the day at Old Sturbridge Village exploring a more settled lifestyle when American craftsmanship and ingenuity became commonplace.  Our final stop – Hancock Shaker Village – samples utopian, religious life including a traditional Shaker style meal in the Meeting House.  This is a three-night tour program.

Great Estates

This tour program explores the great estates built during the mid 1800’s through the early1900’s, along the Hudson River, Berkshires and Saratoga.  Often called “cottages,” these summertime homes were playgrounds and resting spots for America’s elite families such as the Vanderbilts and Westinghouses.  Explore grand architectural masterpieces, outstanding views and lifestyles long gone.   Three to five-night programs.

New England Maritimes

New England history is first a story of the sea for that is how the very first settlers arrived here.  This tour explores that heritage from the New Bedford Whaling National Historical Park and Whaling Museum to Cape Cod, Boston and the North Shore of Boston, Massachusetts.   This program is four nights.

Mountains & Sea

This four or five night tour program combines the best of the mountains and the coast.  Groups explore a variety of places to give a complete vision of New England.  Visits include famous New England authors’ homes, whale watching and living history museums. 

Historic Hotels

 Stay in three popular historic hotels and discover old world charm again.  These stately properties define what hospitality meant decades ago and today.   Choose between the Red Lion Inn in Stockbridge, MA, Hotel Northampton in Northampton, MA, Middlebury Inn in Middlebury, Vt and the Gideon-Putnam Hotel in Saratoga, NY.  A great selection of attractions at each destination ensures your group’s satisfaction with their visit.  This tour is offered year round.

National Pastimes – Baseball and Basketball Hall of Fame

Who doesn’t like to watch two of America’s favorite pastimes every now and again (or even all day)?  This program visits the Baseball Hall of Fame in Cooperstown, NY, the new Basketball Hall of Fame in Springfield, MA and other attractions.  During the summer, we include tickets to a minor league baseball game.  Sports fans surely won’t be disappointed.  Two nights.

Antiquing in New England

Join us in May, July and September during the Brimfield Art & Antiques Fair.  This is the place to pick up that rare find you’ve always wanted for your home or office.  Before starting out, our resident antique expert gives the group a stimulating talk about the how’s and why’s of buying antique furniture and art.  One to three-day tour program.  Includes some sightseeing.





Theater and Music Tours
Tanglewood Music Festival

Boston Pops

Join us for an evening of splendid sounds with one of the world’s greatest orchestras.  Conductor Keith Lockhart leads the Boston Pops orchestra through some of America’s favorite scores and patriotic tunes.  One or two night programs.

Music, Dance & Theatre Performance Series

During the summer, the Berkshires come alive with theatre, music and dance.  This tour includes all three during a four-night visit.   Sightseeing and relaxing afternoons are included during the day.

Classical Music Immersion at Tanglewood

A very special tour devoted to the listening pleasures of classical music.  Designed to introduce guests to the structure of music, and the personalities that created a sound that has not lost its luster over the last three centuries.  Professor of Musicology, Jeremy Yudkin, the author of two extremely popular books about understanding music, leads this tour.  Professor Yudkin’s talks are entertaining and informative.  The tour’s focal point is the music being played at the Tanglewood Music Festival.  Learn just why Beethoven’s Ninth Symphony sounds so good!  Two to four night programs.

The Show Must Go On...

Some of the best theatre anywhere is found in small villages that dot the New England landscape.  And the Berkshires are full of nationally known theatre companies including the Williamstown Theatre Festival, Stockbridge Theatre Festival and Shakespeare & Company.  Tour programs from two to four nights are available.  This program makes a great Hub & Spoke tour for a greater selection of performances.



Cultural Tours

New England Museums
Degas Sculpture
at the Clark Museum

Meet the Artist

This very special tour gives groups the chance to meet the artists and artisans that create the works we so admire.  We visit artist’s studios and see demonstrations on sculpting, pottery making and other art forms.  Programs vary in length between two and four nights in the Berkshires and Pioneer Valley.  We can even arrange a “hands on” demonstration at a local art school.


Literary Tours

If your group is full of bookworms, they will certainly appreciate visiting the homes and historical sites of some of New England’s greatest writers.  Emily Dickinson, Mark Twain, Hermann Melville and Henry David Thoreau are just a few of the authors the group will study to learn why their writings remain important for us today.  Three to five night programs.




Specialty Tours

Theater and Music Tours
Williamstown Theater Festival

Natural History

Who doesn’t love nature?  Take a lovely stroll around a pristine pond keeping an eye out for beaver.  Learn about bats and birds from a local naturalist.  Study wildflowers in the spring.   Go whale and seal watching on the coast.  Look for bald eagles at Quabbin Reservoir.  Visit the New England Aquarium in Boston.  Tour programs customized from two to five nights in various locations.

Soft Adventure Programs 

Our company was founded in 1989 as Berkshire Hiking Holidays, which I think says something about designing tour programs for groups that desire physical stimulation as part of their tour.  We offer canoe and kayak, walking and hiking, white and flat water rafting, bicycling, skiing and snowshoeing tours.   Of course, the soft part is staying at nice cozy inns serving great food to fuel the next day’s adventure.  Limited to groups of 20 persons.

Epicures Delight

Travel and dine at some of the best restaurants in New England.  These places are known for outstanding food, ambience and service.  Stimulating lectures on various food topics and visits to wineries and breweries are included.  A complete immersion in food, glorious food!  Strictly limited to 25 persons.  A gourmand’s delight.


Main Street Stockbridge – Norman Rockwell Christmas

A painting in the main gallery of the Norman Rockwell Museum depicts Stockbridge, MA in the 1950’s.   In 2004, Stockbridge hasn’t changed much.  This weekend tour program explores the recreation of Rockwell’s painting complete with period cars aligned along Main Street in Stockbridge.  A luminaria walk, caroling, holiday theatre performance and special holiday concert are all part of the program.  Two or three nights.


Food & Drink

This tour is a sampling of our favorite restaurants, wineries and breweries in New England.  A unique experience allowing guests to explore a variety of cuisines with menus specifically designed for our groups.   This is a chance for chefs to show off and they love it.   Includes lunches, dinners and special presentations.  Programs for three nights or longer.

Super Saver Tours

Travel can be expensive – especially if you want to stay in nice hotels, eat good food and fully explore more than one destination.   This two, three or four night program takes advantage of shoulder season touring, which has many advantages including less crowds, better pricing and service.  This tour is offered in March, April, May, November and December. 



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