Let me just start by saying…I LOVE THE BERKSHIRES! They’ve been on my bucket list for awhile. Not because Dorinda from The Real Housewives of New York raves over it, but because it represents the fall to me. The Berkshires is a rural region in the mountains of western Massachusetts and sits in-between New York City and Boston, making it an easy drive for a weekend destination. The Berkshires offers numerous activities for extended stays, from hiking and lake days, to lead peeping or other cultural events.
We spent the majority of our time in the small town of Stockbridge, but visited Lenox, Lee, and Otis, as well. The drive to and from each town is quite magical, yet very relaxing at the same time.
Apparently, fall in The Berkshires is an experience not to be missed, so I WILL be back. Knowing how charming the Berkshires are during summer, I can only IMAGINE how incredible it is when the leaves are golden orange and mustard yellow. Even though it’s based in Connecticut, I felt like I was walking around the set of the Gilmore Girls in Stockbridge! I need to go back and wear cozy sweaters, blanket scarves, and step on some crunchy leaves as soon as possible.
STOCKBRIDGE, MASSACHUSETTS
WHO THIS TRIP IS PERFECT FOR
This trip is perfect for the Gilmore Girl lover who wants a fall experience in a quiet town where they can visit museums, go on beautiful tree-filled hikes, and read a novel by Edith Wharton.
WHERE TO STAY
- HIGHLY recommend staying at the Red Lion Inn
- Chambery Inn (in Lee, MA)
- Miraval Berkshires Resort & Spa
WHAT TO DO
- Take a tour of Edith Wharton’s house and travel back in time. Highly recommend!
- Walk/hike the Mary V Flynn Trail
- Walk around Main Street and visit the locally owned shops and restaurants
- Grab a drink at The Lion’s Den, a historic speakeasy
- Visit Naumkeag, a public garden and historic home
- Tour the Norman Rockwell Museum
- Go kayaking or have a lake day
WHERE TO EAT/DRINK
- Dinner at Widow Bingham’s Tavern at the Red Lion Inn
- Dinner Once Upon a Table
- Breakfast at The Lost Lamb (I’m still craving their gluten free cinnamon roll muffin)
- Lunch at Main Street Cafe
- Drinks at The Lion’s Den
- Ice cream and cheese at High Lawn Farm for a true dairy farm experience
HOT TIPS
- Grab a rental car! It’s much easier to get around yourself than to rely on public transportation here.
- You can fly into New York airports, but I recommend flying into Boston if you prefer an International Airport over a smaller one.
- Make reservations at restaurants! They book up quickly.
- Bring bug spray if you’re visiting during the summer. I learned this lesson the hard way!
- If you have the option to get a muffin grilled, DO IT.
- It’s a very casual, yet affluent area. Dress accordingly.
- Don’t turn down ice cream. Try every shop you come across!
