undefined Itinerary

Spend the morning exploring the historic downtown area of Great Barrington, filled with charming boutiques, art galleries, and antique shops. Then, head to the Berkshire Botanical Garden for a leisurely stroll through the beautiful gardens and grounds.

For lunch, try the Berkshire Mountain Bakery for fresh-baked breads, pizzas, and pastries. After lunch, head to the nearby Butternut Ski Resort for some outdoor adventure, including skiing, snowboarding, and tubing in the winter, and hiking and mountain biking in the warmer months.

After a day of outdoor activities, relax with a glass of wine and some small plates at Allium Restaurant and Bar, featuring farm-to-table cuisine and a cozy atmosphere.

Start the day with a visit to the Barrington Stage Company, a Tony Award-winning theater company showcasing a variety of productions throughout the year. Then, head to Lake Mansfield for a morning of kayaking or paddleboarding on the peaceful lake.

For lunch, try the Berkshire Co-op Market for organic and locally sourced groceries, as well as a delicious deli and cafe. After lunch, explore the historic and picturesque town of Stockbridge, home to the famous Red Lion Inn and the Norman Rockwell Museum.

In the evening, catch a movie at Triplex Cinema, a classic movie theater featuring a mix of independent and mainstream films.

Spend the morning exploring the nearby Appalachian Trail, featuring stunning views of the Berkshires and a variety of hiking and walking trails. Then, head to the Berkshire Museum for a cultural experience, showcasing art, science, and history exhibits.

For lunch, try the Prairie Whale for farm-to-table cuisine featuring local ingredients and a cozy atmosphere. After lunch, check out the local craft breweries, including Big Elm Brewing and Wandering Star Craft Brewery, for some delicious beer tasting.

In the evening, enjoy a delicious dinner at the Castle Street Cafe, featuring live jazz music and a menu of American and international cuisine.

Start the day with a visit to the Mahaiwe Performing Arts Center for a morning of yoga and meditation, followed by a healthy breakfast at the Fuel Coffee Shop. Then, head to the Berkshires Yoga and Wellness Center for a relaxing massage or yoga class.

For lunch, try the Xicohtencatl Mexican Restaurant for authentic and delicious Mexican cuisine. After lunch, explore the nearby Catamount Ski Resort for some outdoor adventure, including skiing, snowboarding, and tubing in the winter, and hiking and mountain biking in the warmer months.

In the evening, enjoy a delicious dinner at the John Andrews Farmhouse Restaurant, featuring farm-to-table cuisine and a beautiful setting.