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Roam Around

5 Days in the Berkshires Massachusetts Itinerary

Last updated: 2024 Jun 14

Exploring Lenox

Morning

Start your day with a delicious breakfast at Haven Cafe & Bakery, known for its fresh pastries and coffee. After breakfast, visit the historic The Mount, Edith Wharton's Home, where you can explore the beautiful gardens and learn about the life of the famous author.

Afternoon

Head to Ventfort Hall Mansion and Gilded Age Museum for a glimpse into the opulent lifestyle of the Gilded Age. Enjoy lunch at Nudel Restaurant, which offers a farm-to-table dining experience with locally sourced ingredients.

Evening

In the evening, take a leisurely stroll through downtown Lenox and have dinner at Brava, a cozy spot known for its tapas and extensive wine list.

Bedtime

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Art and Nature in Stockbridge

Morning

Begin your day with breakfast at Once Upon a Table, a charming cafe in Stockbridge. Then, visit the famous Norman Rockwell Museum, home to an extensive collection of works by the beloved American illustrator.

Afternoon

Have lunch at Red Lion Inn, an iconic establishment offering classic New England fare. Afterward, explore the beautiful grounds of Naumkeag, a historic estate with stunning gardens and architectural features.

Evening

For dinner, head to Main Street Cafe for some hearty American cuisine. End your day with a relaxing evening walk around Stockbridge's quaint streets.

Bedtime

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Cultural Day in Williamstown

Morning

Start your morning with breakfast at Spring Street Market & Cafe. Then, visit the renowned Clark Art Institute, which features an impressive collection of European and American art.

Afternoon

Enjoy lunch at Mezze Bistro + Bar, known for its contemporary American dishes made from local ingredients. Spend your afternoon exploring the beautiful campus of Williams College and visiting its art museum.

Evening

Dine at Coyote Flaco for some delicious Mexican cuisine. In the evening, catch a performance at the acclaimed Williamstown Theatre Festival if it's in season.

Bedtime

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Outdoor Adventures in Great Barrington

Morning

Have breakfast at Prairie Whale, known for its farm-to-table menu. Spend your morning hiking up Monument Mountain for breathtaking views of the Berkshires.

Afternoon

After your hike, have lunch at Baba Louie's Sourdough Pizza, famous for its unique pizza offerings. In the afternoon, visit Lake Mansfield Park for some relaxation by the water or rent a kayak to paddle around.

Evening

For dinner, enjoy a meal at The Prairie Whale again as it offers different menus throughout the day. End your evening with drinks at The Well Restaurant + Bar.

Bedtime

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Relaxation Day in Pittsfield

Morning

Begin your final day with breakfast at On A Roll Cafe. Visit Hancock Shaker Village to learn about Shaker life and see their beautifully preserved buildings and gardens.

Afternoon

Have lunch at Dottie's Coffee Lounge before heading to Arrowhead Museum, Herman Melville's former home where he wrote Moby-Dick.

Evening

'Enjoy dinner at Mazzeo's Ristorante' before catching an evening show or concert if available.

Bedtime

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