Answer: Driving the Mohawk Trail (Route 2) in Massachusetts is a beautiful way to experience the state's natural beauty, especially in October when the fall foliage is at its peak. There are plenty of places to stop along the way, offering scenic views, local charm, and some great spots for food and coffee. Below are some recommendations for your trip from Williamstown to Boston:

Answer: Spending three days in Pittsfield over Thanksgiving weekend offers a charming mix of history, art, outdoor activities, and excellent dining. Pittsfield is the largest city in the Berkshires and serves as a convenient base for exploring the surrounding area.

Answer: Welcome to Lenox! The Berkshires is a beautiful area, and even in the winter, there are plenty of family-friendly activities to enjoy. Since you’ll be visiting in February, here are some ideas that will be great for your kids and easy to access with a car:

Answer: Great Barrington in the Berkshires is a charming town that embraces Halloween, and even though it’s a smaller community, there are usually fun activities for families and trick-or-treaters. Late October weather in the Berkshires can be cool, so it’s a good idea to dress warmly and plan for outdoor activities accordingly.

Answer: Yes, Uber and Lyft are viable options for getting to and from Albany Airport (ALB) and Lenox/Pittsfield for Tanglewood during the summer. However, there are some important things to consider:

Answer: Your concern about staying in Pittsfield, MA is valid — no place is perfect — but it’s helpful to look at the data and local context to get a balanced sense of what to expect. Pittsfield does have higher crime rates compared with many towns in Massachusetts, but many residents and visitors say “crime depends a lot on the neighborhood and how you behave.” I’ll walk through what the statistics show, what’s meaningful on the ground, and how a short stay could still be reasonably safe — with some common-sense precautions.