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Sample Family Itinerary

Posted on December 10, 2015Written by Lindsey Schmid


Arrive in the Berkshires

Overnight Lodging Check-in – Jiminy Peak

Jiminy Peak Mountain Resort is the largest ski and snowboard resort in southern New England, summer home to Mountain Adventure Park and the only mountain resort in North America to generate its own energy using alternative wind power. Jiminy features extensive conference and wedding facilities for groups up to 400 people. Since opening in 1948 Jiminy Peak has evolved to become a 4 season resort, offering something for everyone. While at Jiminy Peak, make sure to make time to visit their Adventure Park and Aerial Park. Jiminy Peak Mountain Adventure Park and Aerial Adventure Park are fantastic for the whole family. There is an alpine slide as well as a new mountain coaster, along with a rock wall, a giant swing and an aerial park that is great for ages of 6 and up. All of Jiminy Peak is great/fun for kids!

Lunch Lickety Split – MASS MoCA

Yum, yum this is a delicious spot for the whole family to enjoy. Café fare, homemade soups, quiche, desserts. Join us in café or eat under the upside down trees! Espresso bar & homemade Herrell’s ice cream!

Afternoon Tour – MASS MoCA

Since opening in 1999, MASS MoCA has become one of the world’s premier centers for making and showing the best art of our time. With annual attendance of 120,000, it ranks among the most visited institutions in the United States dedicated to new art. More than 80 major new works of art and more than 50 performances have been created through fabrication and rehearsal residencies in North Adams, making MASS MoCA perhaps the most fertile site in the country for new art. The museum thrives on making and presenting work that is fresh, surprising, and challenging. Kidspace at MASS MoCA is a not to miss for families. It is a contemporary art gallery, studio, and educational programs promote the understanding and teaching of art through experiential learning opportunities designed for elementary and middle school students, teachers, and families.

Dinner & Show – Williamstown Theatre Festival

WTF Picnics on Family Friday nights, include picnicking and free tickets! Bring a picnic and join other families on the front lawn before curtain. Then it is, buy one Main Stage adult ticket at full price and a child is free. Perfect for the summer musical! Through 56 years, the Festival’s goals remain constant: to attract top talent, cultivate young artists, produce reinterpreted versions of classics and new plays from gifted playwrights and to continue to attract audiences with the quality and ambition of our work.


Breakfast – Bascom Lodge

Enjoy a leisurely drive up Mt. Greylock. Eat breakfast at Bascom Lodge, a rustic 1930’s arts & crafts lodge. Hike or enjoy the view atop Mt. Greylock. At 3,491 feet, Mt. Greylock is Massachusetts highest peak. The Mount Greylock State Reservation, which surrounds Bascom Lodge, covers more than 11,000 acres. Hikers can enjoy 50 miles of trails over a variety of terrain, including a section of the Georgia to Maine Appalachian Trail. For those who enjoy natural history, a variety of birds, trees, mammals and geological formations are found within the park.

Lunch – Baba Louie’s Pizza

Everyone in the family will find something they can enjoy at Baba Louie’s! Every meal served comes from the highest-quality ingredients. Local artisan bakers at the Berkshire Mountain Bakery in Housatonic, MA, provide them with the delicious and nutritious sourdough pizza crusts. We select the freshest veggies, fruits, cheeses, and meats to create our wood-fired pizzas and heaping salads.

Tour – Hancock Shaker Village

Available EVERY day, our hands-on Discovery Room at Hancock Shaker Village offers make-and-take crafts, Shaker costumes to try on, a demonstration beehive, child-sized looms and “Mary Jane” a fiberglass cow that can be milked. Kids 6 and under are free at HSV, and 7 to 12-year-olds only $4. This beautifully restored village, set amongst acres of farm, woodland, and pasture, is home to the premier collection of Shaker buildings and artifacts. Graceful Shaker furniture, crafts, and household items are exhibited in 20 historic buildings, each an architectural gem. The Round Stone Barn, most famous of all Shaker buildings, is a testament to Shaker efficiency, innovation, and design. See the Village come to life through tours, exhibitions, demonstrations, and participatory activities. Talk with artisans working in authentic Shaker shops. Learn about the heritage breed animals that roam the pastures and the heirloom crops in the gardens while soaking up the beauty of Shaker architecture. Sing along to “Simple Gifts.” Your children can even take a lesson with a “Shaker” schoolteacher.

Concert – Tanglewood

Don’t miss the Family concerts that are performed all summer at the Koussevitzky Music Shed. Tanglewood is the summer home of the Boston Symphony Orchestra and the host of summer music education centers. Located on the expansive campus are The Serge Koussevitzky Music Shed, the Boston Symphony Orchestra performance venue designed by local Stockbridge engineer Joseph Franz in 1938, and Seiji Ozawa Hall, built in 1994. Today Tanglewood annually draws over 350,000 visitors. Each season offers not only a vast quantity of music but also a vast range of musical forms and styles, all of it presented with a regard for artistic excellence that makes the festival unique. Performance Jacob’s Pillow Dance Festival

Performance – Jacob’s Pillow Dance Festival

Outdoor “Inside/Out” Performances, Wednesdays-Saturdays 6:15-7pm and are Free to everyone. Of the more than 50 dance companies presented at Jacob’s Pillow in 2011, more than half can be seen performing on Inside/Out, a unique outdoor performance space nestled in the bucolic hills of the Berkshires, for free. The free Inside/Out series includes presentations of emerging dance companies, artists from all over the world, and informal showings by the students of The School at Jacob’s Pillow. Tap dance, ballet, jazz, musical theatre, contemporary, hip-hop, samba and various other dance forms from all over the world are represented every summer. Bring a picnic for the family to enjoy during an Inside/Out performance and share the art form with all generations. All are welcome at Inside/Out, even the family dog Jacob’s Pillow Dance, lauded worldwide as a “hub and mecca of dancing” (TIME Magazine) and “one of America’s most precious cultural assets” (Mikhail Baryshnikov), is a treasured National Historic Landmark and home to America’s longest-running international dance festival.


Breakfast – Haven Café & Bakery

The priority at Haven is food and community. Their mission is to offer high-quality food and excellent service to all of their guests – whether you need a fresh cup of great coffee to go, healthy delicious breakfast to sit down with, tasty life-enhancing meal to take home or if are planning a catered event for dozens of friends and family.

Tour – The Mount, Edith Wharton’s Estate and Gardens

The Mount offers free admission to all kids and teens 18 years. This summer, go on a Scavenger Hunt at the Mount, detective eyes required! Children of all ages are encouraged to explore The Mount through one of our scavenger hunts. Scavenger hunts focus on both the house and gardens and give children the freedom to roam while engaging in careful looking. They must find all the images on the sheet before returning to The Bookstore to claim their special prize. All scavenger hunts are free and suitable for children (and adults) of all ages. Wharton designed and built The Mount in 1902, based on the principles outlined in her influential book, The Decoration of Houses (1897), co-authored with architect Ogden Codman, Jr. This classical revival house represents the only full expression we have of Wharton’s architectural interests. Edith Wharton was an authority on European landscape design as well as a passionate gardener. She envisioned her gardens as an elegant series of outdoor rooms and created unique architectural compositions planned in concert with the house and the surrounding natural landscape. Three acres of formal gardens surround the house.

Complimentary Lunch – The Mount, Terrace Café

Tour – Norman Rockwell Museum

Founded in 1969 with the help of Norman and Molly Rockwell, Norman Rockwell Museum is dedicated to the enjoyment and study of Rockwell’s work and his contributions to society, popular culture, and social commentary. Be sure to roam the grounds and check out the great sculpture and walking trails and then go to the children’s area where you can create your own artwork. The Museum, which is accredited by the American Association of Museums, is the most popular year-round cultural attraction in the Berkshires. The Museum houses the world’s largest and most significant collection of Rockwell’s work, including 574 original paintings and drawings. Rockwell lived in Stockbridge for the last 25 years of his life. Rockwell’s Stockbridge studio moved to the Museum site, is open to the public from May through October, and features original art materials, his library, furnishings, and personal items. The Museum also houses the Norman Rockwell Archives, a collection of more than 100,000 items, including working photographs, letters, personal calendars, fan mail, and business documents. Shopping Lee Premium Outlets

Shopping – Lee Premium Outlets

Of course, no vacation is complete without some shopping and these outlets, right next to the turnpike, are not to be missed, 60 Outlet Stores. Legendary brands. Over 60 designer and brand name outlet stores with everyday savings of 25-65%. If the children need a break while you continue to try on shoes there are Kiddie Rides available near Fragrance Outlet, the rides are located under a shaded gazebo. There are also strollers available to help you get the children around and these are located on the food court patio, Kiddie Kruzzer rentals offer kids the opportunity to choose a “cool” ride in a ladybug, police car, taxi cab and fire truck (fee applies).

Depart the Berkshires

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