Perfect Fall Berkshires Day Trip Itinerary
The Berkshires region of Massachusetts is located in the far western side of the state, bordering New York state. It’s such a picturesque part of the state to visit year-round with beautiful mountains, lots of scenic trails, historical properties, restaurants, and a vibrant arts scene.
I especially love visiting in fall with the cooler temps and the leaves changing colors. You can easily spend multiple days exploring the Berkshires or pack a full day of activities into a single day trip.
This Berkshires Fall Day Trip Itinerary covers the central Berkshires region including Stockbridge, Lenox, Lee and Richmond.
Welcome to the Berkshires!
But First, Coffee - West Stockbridge
Start the day with a coffee or latte from small batch coffee roasters No. Six Depot located in West Stockbridge. This is my favorite coffee shop in the Berkshires! They always have delicious coffee beverages and pastries too. And for my gluten free friends - this spot has an amazing selection of gluten free baked goods! I had a gluten free morning glory muffin on my visit and it was amazing. And on top of the deliciousness this spot has to offer, they have fabulous decor and great indoor and outdoor seating options.
Cider Donuts and Apple Picking - Richmond
Enjoy the freshest cider donuts from Hilltop Orchards - so fresh that you can actually watch your donut be made! Then head out into the orchard for apple picking with beautiful mountain views. Hilltop Orchards also offers wine and cider tastings.
Normal Rockwell Museum - Stockbridge
Visit the Norman Rockwell Museum which houses the largest collection of Norman Rockwell’s art.
Explore the museum, take a self guided studio or gallery tour, and walk the trails located on the property.
The Mount, Edith Wharton’s Estate - Lenox
Walk through the beautiful gardens at The Mount, Edith Wharton’s Estate and explore the hiking trails on the property.
This historic property was once the home to Edith Wharton who designed and built the estate in 1902 along with architect Ogden Codman. The two also partnered together to publish the interior design book, “The Decoration of Houses,” which is still relevant today. Edith has several other published works as well, which you will find in the estate today. The home is open for ticketed tours daily through the end of October and on weekends in November - December.
The outdoor grounds and gardens are free to explore and open daily from dawn to dusk. From the parking lot at the main entrance, it’s just a short walk to the house. Visitors can opt to take the main road or a trail through the woods.
After exploring the beautiful gardens of the estate, continue on past the gardens to explore more hiking trails, including the Beaver Pond Loop trail. This trail takes you through the woods and fields along the pond. The trails are very well maintained and marked.
Ice Cream at High Lawn Farm - Lee
Enjoy an ice cream at High Lawn Farm including seasonal rotating flavors like apple crisp or pumpkin. The farm uses milk from their own cows who you can meet while visiting. They also serve grilled cheese and cheese boards and offer a variety of items for purchase. In the fall there is also an amazing selection of pumpkins for purchase.
A Gilded Age Museum - Lenox
Tour the Ventfort Hall Mansion and Gilded Age Museum. This 1893 mansion continues to be restored and provides visitors with an opportunity to travel back in time. The home was originally built in 1893 for Sarah Morgan, the sister of JP Morgan. At that time the home had 28 rooms including 15 bedrooms.
Venfort Hall is open daily from 10 am to 4 pm for self-guided tours. Admission is $18 for adults and $7 for children.
Balderdash Cellars - Richmond
Sample delicious wines at Balderdash Cellars while taking in some beautiful views. My favorite wine was the Sauvignon Blanc. (Richmond)
Naumkeag Pumpkin Show
Close out a perfect day in the Berkshires with the Incredible Naumkeag Pumpkin Show, located on the beautiful historic Naumkeag property maintained by The Trustees. Naumkeag is an incredible 44-room Gilded Age style home that sits at the top of this property, high on the hill for the perfect view of the mountain range. The home is a really unique design and you can learn more about the construction and style of the build on the Architecture tour.
The home was built in 1884 for Joseph Choate, a prominent New York attorney, and his wife Caroline. Since then, Naumkeag was home to several generations of the Choate family. Thanks to their daughter Mabel Choate, who transferred the property to The Trustees in 1958, the public can now enjoy this beautiful space.
The annual Pumpkin Show at Naumkeag features over 1,500 jack-o-lanterns along with 100s of mums and pumpkins. The pumpkins are all hand-carved by staff and volunteers at Naumkeag and the designs are absolutely amazing. There is a concession stand open with local cider donuts and fresh apple cider. You can also tour the first floor of the inside of the home.
