I've lived my entire life in Berkshire County, and I know it’s easy to get lost in its own beauty. Winter, spring and summer all have their own special traits and qualities. I think, however, if you were to ask anyone who’s lived or visited this area they’d say fall is the best time of year. This year the fall equinox was September 22nd, though Indigenous Peoples Day is usually the biggest day of the season, with peak foliage falling around the first two weeks of October. Berkshire County has a plethora of places to see, food to eat, and drinks to… drink. Route 7, running north to south, is the spine of the county. It’s the main connector from Vermont to Connecticut. Most towns and cities in Berkshire County are not far off this main route. Almost all the stops I’ll talk about can be found not more than a five to ten minute drive from this central artery.
The first place to stop and look around is the highest point in Massachusetts: Mt. Greylock Reservation at 3,491 feet. From its peak on a clear day, you can see as far as 90 miles away. No matter when you visit, there's plenty to do and see. The park is open from dawn to dusk. For more information you can visit the mass.gov webpage about it.
As you continue south on Rt. 7 you’ll run into Stockbridge, home to the Norman Rockwell Center. Rockwell’s “Main St. at Christmas” is one of the most famous paintings in Berkshire County history. You’ll also find Chesterwood, home of sculptor Daniel Chester French who sculpted the Lincoln Memorial. Both these museums are perfect to visit during Fall as they are in the middle of peak forest conditions. Take a moment and visit the porch of the Red Lion Inn on Main St and enjoy a hot toddy. The red wicker chairs are worth the price of admission. It’s one of the longest standing hotels in the United States—some parts of the building are from 1773. Down the street, the Mission House will teach you about the Mohicans who lived on this land before any of us.
Our heart always seems to be in Great Barrington. Which is home to another peak one needs to climb. Monument Mountain is, famously, where Nathaniel Hawthorne and Herman Melville first met. They both called Berkshire County home. From the top of Monument Mountain, you can see three states.
Fall Festivals are in great demand in Berkshire County. There’s the Lenox Apple Squeeze in Lenox, the Harvest Festival in Stockbridge, the Lee Founders Celebration in Lee, and Fall Foliage Parade in Pittsfield. If it's food and gifts you crave you will not be disappointed. Falling in between the end of September and beginning of October, these four festivals define a true fall celebration. Parades, antiques, homemade goods, games, and—do not forget—food and beverages. Attending these celebrations is cherry on top of the fall atmosphere of Berkshire County.
Apple picking is a ritual deeply rooted in Berkshire County lore. There are many opportunities to dive into our local delicacy. These are three of the most popular places to get your apple picking itch scratched. Each has many activities and choices for taste buds craving locally grown apples.
Once you have experienced fall in the Berkshires you will surely be back year after year. No vacation anywhere else at any other time of the year is like our fall spectacular.
