Pioneer Travel in the Berkshires


Created for alumni and friends of Saint John’s High School, the Pioneer Travel Program is a great new way to connect with good friends, meet fellow alumni and enjoy a vacation weekend with the Saint John’s community! What makes Saint John’s special is the incredible connection our alumni feel toward our community, and the Pioneer Travel Program is our way of extending that connection even further.

Bring your spouse, invite your Saint John’s friends and join us for 4 days and 3 nights in the Berkshires — July 16-19, 2020! A group of 15-25 alumni, staff and friends will spend time exploring classic New England towns, visiting the region’s best museums, taking in a concert at Tanglewood, seeing plays at the Williamstown Theatre Festival, dining at wonderful restaurants and golfing at the Berkshires’ best course. 

This all-inclusive Berkshires trip starts and ends at the Saint John’s campus in Shrewsbury, where tour guides will provide luxury van transportation for the week. Take a look a the full itinerary below! Call us at 833-641-0855 or reserve your spot using the form at the bottom of this page.


Day 1: Thursday, July 16

9:30am: Welcome Introduction at Saint John’s High School

We’ll kick off the trip with a welcome reception at the school where you’ll meet the other alums on the trip and get an overview of the weekend from our two expert trip leaders. 

10:45am: Depart for the Berkshires

Transportation for the week is in luxury Mercedes vans.

12:30pm: Arrival at the Norman Rockwell Museum for lunch

We’ll have lunch set up on the patio of the museum, enjoy sandwiches and salads catered by No. Six Depot.

2:00pm: Visit the Norman Rockwell Museum

The Norman Rockwell Museum is home to the world’s largest and most significant collection of Rockwell art. We will take a private guided tour to see many of the 998 original Rockwell paintings and drawings in the museum. After the tour, you will have time to explore the summer exhibits on your own and take in the scenic views around the campus.

4:00pm: Relax at The Birchwood Inn

The Birchwood Inn will be your home for the night. The Inn is the oldest deeded home in Lenox turned into a beautiful Bed & Breakfast located within walking distance of downtown Lenox. Take some time to relax before the evening performance!

6:00pm: Dinner at Bistro Zinc

Enjoy dinner at this modern French bistro that boasts locally inspired cuisine and a warm atmosphere.

8:00pm: Performance at Tanglewood

Tanglewood has been the summer home of the Boston Symphony Orchestra since 1937. Year after year, memories are made at the famed music venue! 

Day 2: Friday, July 17

7:30am: Breakfast at the Birchwood Inn

A delicious breakfast will be served in the dining and parlor rooms of the inn!

10:00am: Edith Wharton’s “The Mount”

A Berkshires landmark and the former home of Pulitzer Prize winning author Edith Wharton, The Mount includes sprawling gardens on over 113 acres in Lenox. You’ll take a private guided tour of the mansion and have time to explore the gardens on your own. (Pictured in the header — photo credit: Sarah Kenyon)

12:00pm: Al Fresco Lunch on the Terrace

Lunch will be served on the Terrace for you to enjoy the views of the gardens and grounds.

2:00pm: Golf at Taconic or a Private Tour of Mass MoCA

Choose to enjoy 18 holes at Taconic Golf Club, the premier course in western Massachusetts. Taconic provides golfers with a magical combination of spectacular scenery, a classically challenging course and superb playing conditions. 

Alternatively, you can choose to visit the Massachusetts Museum of Contemporary Art (Mass MoCA) for a private tour of the expansive 250,000 square foot museum. The museum includes one of the largest open space exhibits in the world, all in a uniquely renovated historic mill building.

4-6:00pm: Relax at the Williams Inn

Your luggage will be waiting in your rooms at the Berkshire’s newest hotel, the Williams Inn. The Inn, located in downtown Williamstown, has been designed to reflect the architecture of local area farms, built of stone and wood. 

6:30pm: Dinner at The Barn

We’ll enjoy dinner at The Barn, a new restaurant in the Williams Inn, offering locally-sourced classic American cuisine.

8:00pm: Performance at the Williamstown Theatre Festival

Since 1955, the Williamstown Theatre Festival has brought America’s finest actors, directors, designers and playwrights to the Berkshires. Past performances include Gwyneth Paltrow, Sigourney Weaver, Bradley Cooper, Paul Giamatti, Matthew Broderick, Uma Thurman, Jesse Tyler Ferguson and more!

Day 3: Saturday, July 18

7:30am: Breakfast at the Williams Inn

Enjoy a wonderful breakfast at the Inn, and take some time to walk through the town at your leisure.

10:00am: The Clark Art Institute

Known for its intimate galleries and stunning natural environment, The Clark is a must-see on any Berkshires visit. We will take a private guided tour of the permanent collection, which will be followed by time to explore and experience the summer exhibitions in the other galleries.

12:30pm: Lunch by the Three-tiered Reflecting Pool

Lunch will be available on your own in the museum’s cafe, which we encourage you to enjoy beside the three-tiered reflecting pool in the rear of the museum. You will have further time to explore the galleries or walk the scenic trails behind the Clark following lunch.

2:00pm: Matinee Performance at the Williamstown Theatre Festival

After seeing the Nikos Stage production on Friday night, we’ll take in the main stage performance today!

5:00pm: Relax at the Williams Inn

Relax and unwind at the Inn, or stroll through town at your leisure. Use this time to get ready for dinner.

7:30pm: Dinner at Mezze Bistro

Our farewell dinner as a group, where we will be joined by Headmaster Alex Zequeira, Warren Hayden, Director of Alumni Relations & Planned Giving, and John Ermilio, Chief Advancement Officer. Mezze is a Blank Canvas staff favorite with refined American plates, craft cocktails and boutique wines. 

Day 4: Sunday, July 19

7:30am: Breakfast at the Williams Inn

Enjoy a wonderful breakfast at the Inn, and take some time to walk through the town at your leisure.

8:30am: Mass at Saint Patrick and Raphael Roman Catholic Church

A merger between two Catholic churches in Williamstown, these two churches have served the spiritual needs of Williamstown for more than 130 years.

10:00am: Visit to the Williams College Museum of Art (WCMA)

WCMA offers a growing collection of more than 14,000 works with strengths in contemporary art, photography, prints and Indian painting. We’ll take a private guided tour of the museum.

12:30pm: Lunch at Spring St. Market

Enjoy lunch in Williamstown and walk through campus before we depart. Following lunch, we’ll head back to Saint John’s with an estimated arrival of 3:30 pm.

Pioneer Travel Reservation Form