Sample Itineraries

Looking for inspiration? Then take a look at our sample itineraries and starting planning your groups Berkshire itinerary today.


Are you looking to get out and move? Then get to the Berkshires and discover our great outdoors that rivals any place in the world. There will never be a dull moment whether you only have time to do a hike to wind down your day or whether you are looking for a day full of swimming, zip lines and bird watching. We have it all.

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Performing Arts

The performing arts in the Berkshires are truly world class. We are the summer home of the BSO at Tanglewood and our theater and dance venues make us one of the cultural meccas of the United States. Any itinerary in the Berkshires must include a visit to one of our outstanding performing art venues, so whether you are here for ½ a day, a day, a week or longer be sure to order your tickets today.

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Museums & Historic Sites

When visiting Massachusetts be sure the Berkshires is on your itinerary or else you will miss out on a chance to experience our rich culture of museums & historic sites. From world-class modern art to gilded age “cottages” the Berkshire’s has something for everyone’s taste.

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DAY 1 – 10:00 AM

Arrive in Lenox, MA located in the heart of the Berkshires and Enjoy Breakfast at 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 they need a fresh cup of great coffee to go, a healthy delicious breakfast to sit down with, a tasty life enhancing meal to take home or if they are planning a catered event for dozens of friends and family…

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DAY 1 – Overnight Lodging Check-in at 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…

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