Bennington, VT, USA to Pittsfield, MA, USA from $10: 3 ways by bus, train, flight or car

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Get detailed, step-by-step directions below for your trip from Bennington to Pittsfield with 1Map travel planner. Easily compare ticket prices, explore various transport options, and find the best routes for a seamless and cost-effective travel experience.

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1h  15m

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2h  30m

Estimated price

$10-15

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Distance: 32 km

Duration: 1h 15m

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Average Duration

2h  15m

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Traveling From Bennington to Pittsfield

The journey from Bennington to Pittsfield offers a delightful contrast between the charming Vermont landscapes and the vibrant cultural scene of this Massachusetts city.

Best Neighbourhoods in Pittsfield

Pittsfield boasts vibrant neighborhoods, each offering unique experiences.

Downtown Pittsfield

• Home to lively arts and cultural events.

• Diverse dining options and local shops.

Lenox

• Known for its historic charm and cultural venues.

• Close to Tanglewood performing arts for music lovers.

Pittsfield State Forest

• Offers beautiful hiking trails and scenic views.

• Perfect for outdoor enthusiasts seeking tranquility.

Best Times To Visit Pittsfield's Attractions

Timing your visits can elevate your experience in Pittsfield's highlights.

Berkshire Museum

Weekdays in the morning offer a quieter environment to explore exhibits.

Tanglewood

Attending weekday concerts in July and August avoids large weekend crowds.

Pittsfield State Forest

Visit in early morning or late afternoon for serene hiking and stunning views.

Pittsfield Weather: What to Expect Year-Round

Pittsfield experiences a varied climate, with warm summers and cold winters, making it essential to plan your visit according to the seasons. Spring and fall are ideal for enjoying outdoor activities, while snowfall in winter creates a picturesque backdrop perfect for winter sports.

Dining Recommendation in Pittsfield

Try the braised short ribs at On A Roll, where the vibrant flavors and modern atmosphere create a stark contrast to the more rustic dining options in Bennington. The use of locally sourced ingredients and creative flair here brings a fresh twist to your culinary journey.