8 Reasons to Visit the Berkshires in Late Fall
On a history- and art-filled girlfriend trip, guest contributor Laura E. Kelly finds that the Berkshires region of Massachusetts really shines in October.
The Berkshires area is famous for its vibrant summer arts scene, but because my friend Maureen was traveling from Grand Haven, Michigan, to the East Coast for a wedding in late October, we decided to check out what the Berkshires were like in the fall.
We set out on a four-day adventure focused on the historic Berkshire County villages of Lenox and Stockbridge, drawn by that area’s art, scenic landscapes, and Gilded Age charm.
We hoped for crisp air, colorful foliage, and minimal crowds—and the Berkshires delivered beyond our hopes.
Highlights from Our Late Fall Berkshires Trip
1. Norman Rockwell Museum
We kicked off our visit with a morning at the Norman Rockwell Museum in Stockbridge. This hillside gem has many permanent exhibits, including all 323 Saturday Evening Post covers by Rockwell, plus ever-changing special exhibits.
We loved “Illustrators of Light: Rockwell, Wyeth, and Parrish” from the Edison Mazda Collection, and spotted a fun-sounding upcoming “Jazz Age Illustration” show.
Don’t miss the outdoor sculptures by Peter Rockwell, Norman Rockwell’s son, and Norman’s historic carriage-barn studio, where he worked for the last 21 years of his life (a separate tour ticket is required).
2. Pumpkin Spice Lattés in Stockbridge
Next, we explored Stockbridge’s Main Street, which looked straight out of a Rockwell painting—probably because we’d just viewed the artist’s iconic 1967 “Home for Christmas” painting in the museum! In October, Main Street was festooned with pumpkins instead of wreaths.
Autumn was in full display at Main Street Café, situated in the village’s former general store. Our first pumpkin spice lattés (PSL) there kicked off a three-day informal PSL crawl through the area’s restaurants, hunting for more of those delicious seasonal coffees.
Our Stockbridge day wrapped up with browsing interesting local shops, and then people- and dog-watching from our wicker chairs on the wide porch of the historic Red Lion Inn (founded in 1773 as a stagecoach stop).
3. Leaf peeping at High Lawn Farm
The next morning, a tip from a Berkshires shopkeeper for a “don’t-miss scenic fall drive” led us to High Lawn Farm, outside the nearby town of Lee.
High Lawns is still a working dairy farm, 100 years after Cornelius Vanderbilt’s great-granddaughter built a summer house/estate there.
Near the turreted clock tower on the property, we met Paris, Bon Bon, Fire, and the rest of the pedigreed Jersey girls who provide the milk for all the delicious ice creams and cheeses sold in the farm’s creamery.
In addition to wonderful vistas and cute cows, at the High Lawn farmstead in autumn you’ll find heirloom pumpkin-patch displays, seasonal ice creams, and various fun Halloween events.
4. Edith Wharton’s literary haven, The Mount
After visiting the dairy farm, we drove north a short distance to spend a leisurely afternoon at The Mount, Edith Wharton’s 35-room house (with more than 100 windows!) located on a wooded hill in Lenox.
The American author designed the Mount to her “unfussy” specifications, and it was completed in 1902, towards the latter end of the building frenzy of the Gilded Age summer cottages (they were called “cottages” to downplay their grandeur).
The Mount’s house and gardens had fallen into disrepair by the end of the 20th century, but have now been beautifully restored.
On the interesting three-level guided house tour ($22), we learned all about Wharton’s literary career and love life. She lived at The Mount for 10 years, writing her first five novels there, including bestsellers Ethan Frome and the bittersweet The House of Mirth, before divorcing her husband and decamping to France.
After the formal tour, Maureen and I wandered around the house and grounds while taking far too many photos of the restored gardens and glowing fall vistas. We especially enjoyed browsing The Mount’s unexpectedly large gift shop, featuring items from all over the world.
5. Ventfort Hall — A House and Gilded Age Museum
While The Mount represents a successful restoration of one of the Gilded Age mansions, Ventfort Hall, a short walk from downtown Lenox, offers visitors an interesting glimpse of a restoration-in-progress.
The 50-room Ventfort (French for “strong wind”) Hall was built in 1893 for Sarah Morgan, sister of J. P. Morgan. After a long decline in the house’s fortunes, in June 1997, the house was rescued by the community-run Ventfort Hall Association.
For close to 30 years, the nonprofit has been painstakingly restoring the vast mansion room by room, accepting donations of period furnishings (we saw lots of fainting couches!), as well as establishing a national museum of the Gilded Age within its walls.
We went on an illuminating house tour, starting with the stunning Great Hall and plenty of “before and after” photographs.
We also learned how the 1999 movie The Cider House Rules featured the exterior and some interior shots of the then-neglected Ventfort Hall, giving the house a much-needed injection of Hollywood funds for its reconstruction.
Ventfort Hall features Gilded Age tours, ghost tours, and an intriguing-sounding Masquerade Macabre Ball in October.
6. Naumkeag’s Pumpkin Show
Naumkeag, a well-cared-for Gilded Age estate in Stockbridge with much of its original furnishings and decor, hosts events and tours all year long. The Stanford White–designed brick-and-shingled house has priceless views of rolling hills, complete with grazing sheep.
Add in the Pumpkin Show’s more than 1,500 jack-o-lanterns, hundreds of mums, pumpkins, and countless gourds winding around the exterior and interior of the property in late September and October, and this house visit becomes an autumn-in-the-Berkshires must-do.
We visited festive Naumkeag at 4 pm before all the jack-o-lanterns were illuminated in the evening, so we got a discount on our tickets (proceeds go to support Berkshire Land Conservancy).
7. Naturally, Art
We stopped by the Berkshire Botanical Garden near Stockbridge for a short nature walk, and the salesclerk in the gift store directed us across the street to the Garden’s rather hidden Leonhardt Galleries, situated in a rustic 18th-century house.
There, we enjoyed an extensive and imaginative watercolor painting exhibit called FLOCKS, by artist and book author Robin Crofut-Brittingham, which gave visitors a window into the world of some very colorful, real-life birds.
The friendly docent at the gallery told us there are special art shows with nature themes throughout the year at the Leonhardt Galleries.
8. Lingering in Lenox
One of our favorite things turned out to be just rambling around the walkable village of Lenox while yellow and red leaves drifted down around us.
There were no crowds in late October, and all the Lenox art galleries, book and gift stores, and restaurants were open and welcoming.
Below are just a few of the impressive buildings we saw in a few short blocks.
On our first evening in Lenox, we filled up on delicious salads at Antimony Brewing, just down the road from our hotel on Pittsfield Road. Other nights in Lenox we enjoyed wood-fired Neapolitan craft pizzas at Pizzeria Boema, and signature cocktails and appetizers while lounging by a fireplace at Dulu, the swanky café at the new nine-room Doctor Sax House boutique hotel in one of the village’s former Gilded Age cottages. (We asked: the hotel is named after a Jack Kerouac book.)
Our aforementioned PSL crawl was capped off at Lenox’s Haven Cafe and Bakery.
Even though performance venues like Tanglewood (the summer home of the Boston Symphony Orchestra) and Shakespeare & Company had wrapped up their summer seasons by October, there were still live shows to be seen, including at the WAM Theatre right in downtown Lenox.
Of course, Maureen and I didn’t have a chance to see and do nearly everything on offer in the larger Berkshires region over our four days, but we know one thing for sure: we both would certainly pick October again as the time to visit.
Laura E. Kelly is a New York–based writer and artist and has written previously for More Time to Travel.
IF YOU GO
- The Berkshires hills country in Western Massachusetts and Connecticut is nearly 1,000 square miles, and comprises the larger cities of Pittsfield, North Adams, and Great Barrington, and many smaller towns and villages such as Lenox, Stockbridge, and Lee. The Appalachian Trail intersects several of these towns.
- Lenox, MA, is approximately a 3-hour drive north from New York City, a one-hour drive southeast from Albany International Airport (over the Hudson River and a few mountains), and 2.25-hour drive west of Boston.
- Amtrak’s Berkshire Flyer is a picturesque 4-hour train that travels from NYC to Pittsfield, MA, along the Hudson River. However, at this writing, the Berkshire Flyer train only runs in the summer months, ending in September. There are also trains and buses from Boston. But you would need a tour bus or a car to get to many of the local sites we visited.
- We recommend our hotel, the comfortable and affordable new Element Lenox Berkshires (by Marriott), a 5-minute drive north of Lenox.
-
- We enjoyed a free wine-and-cheese happy hour every night at 5 pm in the Element’s open-plan lobby bar, and were very happy with our free self-serve breakfasts every morning, with everything from yogurt & fruit and fresh-baked goods to tasty scrambled eggs and pancakes cooked by a kitchen chef. Maureen especially loved the state-of-the-art gourmet coffee maker.
-
- The Element Lenox is a long-stay hotel so its rooms come with kitchenettes (handy for stowing away any leftover pizza, we found). The hotel also has an exercise room, indoor pool, and a small self-serve laundry facility.
**Please refer to the Welcome to the Berkshires information website for more trip-planning info.
Save to Pinterest!!
