Berkshires Travel Guide

Explore the best of Berkshires with our comprehensive travel guide, featuring a list of places to visit, hiking and biking routes, food and drink scene, where to stay, and more.


Introduction to Berkshires

Nestled in the heart of New England in Massachusetts, Berkshires is a beautiful region that offers a perfect blend of culture, history, and natural attractions. Surrounded by stunning scenic beauty, this area is home to charming towns, hilltops, and valleys that host an array of activities and adventures. From hiking and biking trails to museums and galleries, to delicious food and drinks, you will find it all in Berkshires.

List of Places to Visit in Berkshires

If you are planning to visit this beautiful region of Massachusetts, here are some of the top places you must visit:

Culturally Important Attractions: Museums and Historical Places

  • The Clark Art Institute
  • Norman Rockwell Museum
  • The Mount
  • Hancock Shaker Village
  • Berkshire Museum

Natural Attractions of Berkshires: Outdoor Adventures and Scenic Views

  • Mount Greylock State Reservation
  • Bash Bish Falls State Park
  • Taconic Trail State Park
  • Wahconah Falls State Park
  • Monument Mountain

Hiking/Biking Routes of Berkshires

Berkshire region is known for its diverse array of hiking and biking trails that are perfect for outdoor enthusiasts. Here are some of the best trails to explore:

  • Appalachian Trail
  • Pine Cobble Trail
  • Monument Mountain Reservation
  • Mount Greylock State Reservation
  • The Ashuwilticook Rail Trail

Best Things to Do in Berkshires: Activities and Tours

Berkshires has something for everyone, and when it comes to activities and tours, there are plenty of options to choose from.

  • Whitewater rafting on the Deerfield River
  • Tanglewood Music Festival
  • Jacob’s Pillow Dance Festival
  • Berkshire Scenic Railway Museum
  • Berkshire Theatre Group

Week-Long Itinerary for Berkshires

If you are planning a week-long trip to Berkshires, here is a sample itinerary to get the most of your visit:

Day Activities
Day 1 Visit The Clark Art Institute, and dine at Cafe Lucia
Day 2 Hike the Pine Cobble Trail and visit Mount Greylock State Reservation
Day 3 Visit the Norman Rockwell Museum and take a scenic drive through The Mount
Day 4 Explore Berkshire Museum and the Hancock Shaker Village
Day 5 Take a guided tour of Berkshire Scenic Railway Museum and attend a Tanglewood Music Festival
Day 6 Take a dance class at Jacob’s Pillow Dance Festival and dine at Nudel Restaurant and Bar
Day 7 Go whitewater rafting on Deerfield River and visit Wahconah Falls State Park

Food and Drink Scene of Berkshires

Berkshires is known for its farm-to-table cuisine and wide range of culinary options ranging from classic New England staples to international cuisine.

Must-Try Dishes

  • Lobster rolls and clam chowder
  • Berkshire Pork
  • Apple Cider Doughnuts
  • Berkshire Mountain Bakery’s bread
  • Grass-fed beef and organic vegetables

Local Beverages

  • Craft beer from Big Elm Brewery and Brewery & Tasting Room, Springside Brewing Company, and Wandering Star Craft Brewery
  • Wine from Balderdash Cellars and Furnace Brook Winery
  • Spirits from Berkshire Mountain Distillers, Inc., and Rubi’s Gin

Where to Stay in Berkshires: Hotels, Hostels, and Guesthouses

From luxurious resorts to cozy B&Bs, here are some of the best accommodations in Berkshires:

  • Blantyre
  • The Red Lion Inn
  • The Black Rabbit Bar & Grille
  • The Inn at Stockbridge
  • The Barrington

What to Buy in Berkshires: Souvenirs and Local Products to Bring Home

Berkshires is a great place to pick up unique souvenirs and local products to bring back home.

  • Handcrafted jewelry from Gray Raven Farm
  • Pottery from Jupiter Pottery
  • Maple syrup and honey from Ioka Valley Farm
  • Artwork from Sohn Fine Art and L’Atelier Berkshires
  • Apparel and sporting gear from the Berkshire Outfitters

Local Culture and Customs of Berkshires

Berkshire culture is unique with a blend of urban and rural lifestyles. The people of the area are welcoming, friendly, and embrace small-town values. Berkshires also has a strong arts and cultural scene, and many of the local customs and traditions are inspired by this.

Best Time to Visit Berkshires

Berkshires is a year-round destination, each season offering a unique and wonderful experience. The best time to visit Berkshires is from June to August when the weather is warm, and many outdoor activities, festivals, and events are in full swing.

Do’s and Don’ts of Berkshires

Do:

  • Hike on designated trails and take care of the natural environment.
  • Respect the privacy of the locals.
  • Attend the region’s cultural and sporting events.
  • Indulge in the farm-to-table cuisine

Don’t:

  • Don’t litter or harm the natural environment.
  • Don’t engage in any activities that are disrespectful or harmful to the local culture.
  • Don’t wander on private properties or disturb local wildlife.

Safety and Health

Safety in Berkshires

Berkshires is a safe place to visit, with very low crime rates. However, it’s always good to take basic safety precautions while traveling, like locking your car and keeping your belongings safe.

Health in Berkshires

Berkshires has several hospitals and medical centers providing health care services for residents and visitors. It’s a healthy and active place, and visitors can take advantage of the region’s outdoor activities to stay fit and healthy.

Getting to Berkshires: Transportation Options and Logistics

Airports Near Berkshires

  • Albany International Airport
  • Bradley International Airport
  • Logan International Airport

Bus Stations Near Berkshires

  • Peter Pan Bus
  • Greyhound Bus

Other Options

  • Private car
  • Taxi

How to Get Around in Berkshires

Berkshires is best explored by car, but visitors can also choose from alternate options like bike rentals or horse-drawn carriages.

Where to Go Next from Berkshires: Nearby Destinations and Excursions

  • New York City
  • Boston
  • Cape Cod
  • Newport
  • Hartford

Conclusion

Berkshires is a beautiful region full of charming towns, outdoor adventures, cultural attractions, and excellent cuisine. Whether you’re a solo traveler, family, or a couple, there’s something for everyone. Plan a visit to this beautiful area, and you won’t be disappointed!



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