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Southern Berkshires Culinary and Cultural Delights Itinerary

Last updated: 2024 Jun 14

Culinary and Nature Exploration

Morning

Start your day with a delightful breakfast at The Red Lion Inn Dining Room, known for its charming ambiance and delicious cuisine. After breakfast, take a scenic drive to the Mount Greylock State Reservation, the highest point in Massachusetts, for a morning hike and stunning views of the surrounding area.

Afternoon

For lunch, head to Mission Bar & Tapas in Pittsfield, a cozy spot with a great selection of small plates. After lunch, visit the Norman Rockwell Museum in Stockbridge to admire the works of this iconic American artist.

Evening

Enjoy a relaxed dinner at District Kitchen & Bar in Pittsfield, known for its farm-to-table cuisine. After dinner, take a leisurely walk around the charming town of Lenox.

Bedtime

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Tanglewood Music and Gourmet Dining

Morning

Indulge in a delicious breakfast at Alta Restaurant & Wine Bar in Lenox, a perfect spot for a leisurely morning meal. After breakfast, spend some time exploring the quaint shops and galleries in Lenox.

Afternoon

For lunch, savor the flavors of Malaysia at Flavours of Malaysia in Pittsfield. After lunch, relax and prepare for the highlight of the day - the Beck concert at Tanglewood Music Center. Make sure to arrive early to enjoy a picnic on the lawn before the show.

Evening

After the concert, enjoy a late-night bite at Barrington Brewery & Restaurant in Great Barrington, a local favorite for its craft beers and pub fare.

Bedtime

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Art and Culinary Delights

Morning

Start your day with a leisurely breakfast at Nudel Restaurant in Lenox, known for its fresh pasta dishes. After breakfast, visit the Mass MoCA in North Adams, one of the largest centers for contemporary visual and performing arts in the country.

Afternoon

For lunch, enjoy a casual meal at Papa John's Pizza in Pittsfield. After lunch, explore the charming town of Williamstown and visit the Clark Art Institute to see its impressive collection of European and American art.

Evening

Dine in style at The Red Lion Inn Dining Room in Stockbridge, a historic setting with a focus on locally sourced ingredients. After dinner, take a leisurely evening stroll through the picturesque streets of Stockbridge.

Bedtime

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Cultural Immersion and Local Flavors

Morning

Enjoy a hearty breakfast at District Kitchen & Bar in Pittsfield, known for its modern American cuisine. After breakfast, visit the The Mount, Edith Wharton's Home in Lenox for a glimpse into the life of the famous author.

Afternoon

For lunch, head to Mission Bar & Tapas in Pittsfield for a unique dining experience. After lunch, take a scenic drive to the town of Adams and visit the Susan B. Anthony Birthplace Museum to learn about the life of the women's rights activist.

Evening

Conclude your day with a memorable dinner at Alta Restaurant & Wine Bar in Lenox, known for its extensive wine list and Mediterranean-inspired dishes.

Bedtime

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Farewell to the Berkshires

Morning

For your last morning in the Berkshires, enjoy a leisurely breakfast at Flavours of Malaysia in Pittsfield, savoring the unique flavors of Malaysian cuisine. After breakfast, take a final stroll through the charming streets of Great Barrington.

Afternoon

Before you depart, have a farewell lunch at Barrington Brewery & Restaurant in Great Barrington, reminiscing about your culinary and cultural adventures in the Southern Berkshires.

Evening

As you bid adieu to this enchanting region, reflect on your experiences over a relaxed dinner at Nudel Restaurant in Lenox, savoring the last moments of your Southern Berkshires getaway.

Bedtime

Find amazing hotels in Southern Berkshires, Massachusetts.