New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

Roam Around

3-Day Berkshires Adventure

3-Day Berkshires Adventure Itinerary

Last updated: 2024 Jun 14

Exploring Nature and Art

Morning
Start your day with a visit to the iconic Mount Greylock, the highest peak in Massachusetts. The panoramic views from the summit are breathtaking, especially in the morning light. Enjoy a leisurely hike along one of the many trails, taking in the natural beauty and tranquility of the area. After your hike, head to Highland Restaurant for a hearty breakfast to fuel up for the rest of your day.
Afternoon
In the afternoon, immerse yourself in art and culture at The Clark Art Institute. This renowned museum features an impressive collection of European and American art, set amidst beautiful grounds. Take your time exploring the galleries and enjoy a stroll through the outdoor sculpture garden. For lunch, stop by Muse Cafe, located within the museum, offering delicious meals with a view.
Evening
As evening approaches, make your way to Tanglewood, the summer home of the Boston Symphony Orchestra. Enjoy an outdoor concert under the stars in this picturesque setting. Before the concert, have dinner at Nudel Restaurant, known for its creative and locally-sourced dishes. End your day with a relaxing evening enjoying world-class music in a stunning location.
Bedtime
Find amazing hotels in Berkshires.
activity-image

Meteora

star4.68

click to access prices

activity-image

Great Ocean Road

star4.85

click to access prices

Historic Charm and Outdoor Fun

Morning
Begin your second day with a visit to Hancock Shaker Village. This living history museum offers a fascinating glimpse into Shaker life with its well-preserved buildings and engaging exhibits. Participate in hands-on activities like traditional crafts or take a guided tour to learn more about this unique community. For breakfast, try Shaker Mill Tavern, which offers classic American fare in a cozy setting.
Afternoon
In the afternoon, head to Berkshire Botanical Garden where you can explore beautifully landscaped gardens showcasing native plants and flowers. It's an ideal spot for nature lovers and those looking to relax amidst serene surroundings. Have lunch at Garden Cafe, located on-site, which serves fresh salads and sandwiches made from locally-sourced ingredients.
Evening
Conclude your day with some outdoor adventure at Ramblewild Adventure Park. Test your skills on their aerial courses or take a peaceful walk through their forest trails if you prefer something less strenuous. For dinner, visit The Old Inn on The Green, offering fine dining in an elegant historic setting.
Bedtime
Find amazing hotels in Berkshires.
activity-image

Blarney Castle & Gardens

star4.53

click to access prices

activity-image

Meiji Shrine (Meiji Jingu)

star4.63

click to access prices

activity-image

Sydney Opera House

star4.68

click to access prices

Cultural Delights and Scenic Beauty

Morning
Start your final day with a trip to Norman Rockwell Museum, dedicated to one of America's most beloved illustrators. Explore his iconic works that capture everyday life in America along with special exhibitions featuring contemporary artists influenced by Rockwell's legacy. Enjoy breakfast at nearby Red Lion Inn, known for its charming ambiance and delicious morning offerings.
Afternoon
Spend your afternoon at Mass MoCA, one of the largest centers for contemporary visual art in North America housed in converted 19th-century factory buildings. The vast space allows for large-scale installations that are sure to impress any art enthusiast. Have lunch at on-site restaurant Lickety Split Cafe which offers casual dining options perfect for refueling during your art exploration.
Evening
End your Berkshires adventure with an evening visit to Jacob's Pillow Dance Festival, where you can enjoy world-class dance performances ranging from ballet to modern dance set against scenic backdrops unique only here! Dine beforehand at nearby restaurantHaven Cafe & Bakery offering delightful meals crafted from local ingredients ensuring both taste buds satisfaction while supporting regional farmers.
Bedtime
Find amazing hotels in Berkshires.
kayakFind the right stay during your trip.
Got a question about your trip?