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undefined Itinerary

Last updated: 2024 Jun 14

Morning
Start your day with a visit to the Tanglewood Music Center, the summer home of the Boston Symphony Orchestra. Take a guided tour of the grounds and learn about the rich history of this iconic music venue. Don't miss the opportunity to explore the beautiful gardens and take a leisurely stroll along the picturesque trails.
Afternoon
Head over to the nearby Berkshire Botanical Garden, a hidden gem in the Berkshires. Discover the stunning array of plants and flowers, and take in the peaceful atmosphere. Enjoy a picnic lunch in the garden and soak up the natural beauty surrounding you.
Evening
For dinner, make your way to The Old Inn on the Green, a historic and charming inn known for its farm-to-table cuisine. Indulge in a delicious meal made with locally sourced ingredients and savor the flavors of the region.
Bedtime
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Morning
Take a scenic drive to Mount Greylock, the highest peak in Massachusetts. Enjoy a hike along one of the many trails and be rewarded with breathtaking views of the surrounding mountains. Don't forget to pack a picnic lunch to enjoy at the summit.
Afternoon
After your hike, visit the Hancock Shaker Village, a living history museum that showcases the unique Shaker culture. Explore the beautifully preserved buildings and learn about the daily life of the Shakers. Don't miss the opportunity to participate in a traditional Shaker craft workshop.
Evening
For dinner, head to the Lion's Den, a cozy pub located in the heart of Stockbridge. Enjoy a delicious meal and live music in a warm and inviting atmosphere.
Bedtime
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Morning
Start your day with a visit to the Norman Rockwell Museum in Stockbridge. Explore the extensive collection of Rockwell's iconic paintings and learn about his life and artistic process. Take a moment to appreciate the nostalgia and American spirit captured in his works.
Afternoon
After your visit to the museum, make your way to the Berkshire Scenic Railway Museum. Take a scenic train ride through the picturesque Berkshire countryside and learn about the history of the railroad in the region.
Evening
For dinner, head to Nudel, a popular farm-to-table restaurant in Lenox. Enjoy innovative and seasonal dishes made with locally sourced ingredients. Pair your meal with a glass of wine from their extensive wine list.
Bedtime
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Morning
Explore the charming town of Lenox, known for its historic mansions and cultural attractions. Start with a visit to The Mount, the former home of author Edith Wharton. Take a guided tour of the estate and gardens and learn about Wharton's life and literary works.
Afternoon
After your visit to The Mount, make your way to the Ventfort Hall Mansion and Gilded Age Museum. Step back in time as you explore the opulent rooms and learn about the social history of the Gilded Age.
Evening
For dinner, head to Alta Restaurant & Wine Bar in Lenox. Indulge in a culinary experience inspired by the flavors of the Mediterranean, complemented by an extensive selection of wines.
Bedtime
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Morning
Start your day with a visit to the Berkshire Museum in Pittsfield. Explore the diverse collection of art, history, and science exhibits, and learn about the region's cultural heritage. Don't miss the opportunity to catch a planetarium show.
Afternoon
After your visit to the museum, make your way to the Colonial Theatre in Pittsfield. Catch a matinee performance of a Broadway show or a local production and immerse yourself in the vibrant performing arts scene of the Berkshires.
Evening
For dinner, head to Mission Bar + Tapas in Pittsfield. Enjoy a variety of small plates inspired by global cuisine, paired with craft beers and creative cocktails.
Bedtime
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