Discover comprehensive travel guides to help you plan the perfect trip to The Berkshires.
Welcome to our collection of travel guides for The Berkshires. These guides will help you discover the best tours, activities, restaurants, and insider tips for your trip.
6 guides · tours, activities & local tips
Experience world-class performing arts and stunning natural beauty in The Berkshires.
Discover charming New England towns nestled amidst rolling hills and picturesque landscapes.
Enjoy farm-to-table dining and artisanal shops showcasing local craftsmanship.
Explore a rich history of artists and writers who found inspiration here.
Immerse yourself in a vibrant community known for its welcoming atmosphere.
Escape to a serene countryside offering both cultural richness and outdoor adventure.
The Berkshires experiences four distinct seasons. Summers are warm and pleasant, perfect for outdoor activities, while autumn brings spectacular fall foliage, crisp air, and cooler temperatures. Winters are cold with snowfall, ideal for cozying up by the fire or hitting the ski slopes. Spring offers a gentle transition with blooming flowers and milder weather.
Late spring through fall, from May to October, offers the most pleasant weather for exploring. July and August are ideal for Tanglewood, while September and October boast stunning fall colors.
Summer, particularly July and August, is peak season. Expect warm weather, bustling cultural events, and larger crowds, especially around Tanglewood and popular attractions.
Winter (December-February) is the off-season, offering fewer crowds and lower prices. While cold, it's perfect for enjoying cozy inns, winter sports, and a quieter, more serene experience.
Save up to 70% on car rentals in The Berkshires when you compare and book in advance.
Discover the best tours and activities in The Berkshires with AI-powered recommendations tailored just for you.