Where to Find 1,500 Carved Pumpkins in the Berkshires

The event you need to add to your fall bucket list: Spend an evening at Naumkeag in the Berkshires exploring a historic Gilded Age mansion surrounded by 1,500 hand-carved jack-o-lanterns.

Each fall I make a trip out to the Berkshires to experience the Incredible Naumkeag Pumpkin Show, and it's easily one of my favorite annual events. This historic property is transformed into a fall display with over 1,500 hand-carved jack-o-lanterns, along with hundreds of mums, pumpkins, and gourds spread across the gardens and grounds.

What is Naumkeag?

Naumkeag is a historic estate in Stockbridge, Massachusetts, set atop a hill looking out to incredible views of the Berkshire Hills, including Monument Mountain.

The property features a 44-room Gilded Age style home, which was built in 1884 as a summer home for Joseph Choate, a prominent New York attorney, and his wife Caroline. Naumkeag was home to several generations of the Choate family.

The house was designed by the renowned architectural firm McKim, Mead & White, with Stanford White playing a key role in its design. It has a distinctive shingle-style design that feels very different from many of the grand Gilded Age estates you'll find throughout New England, like those in Newport, Rhode Island.

The property is best known for its gardens, which were designed in the 20th century by landscape architect Fletcher Steele in collaboration with Mabel Choate. Mabel inherited Naumkeag in 1929 and spent more than three decades working with Steele to create the distinctive garden spaces you can explore today, including the famous Blue Steps.

In 1958, Mabel Choate transferred the property to The Trustees along with many of the Choate family’s household furnishings and fine art. Today, the property is open to the public to explore and enjoy.

And if you’re interested in learning more about Naumkeag, I recommend taking a tour of the property during the summer season, when the house and gardens are open to visitors for general admission, typically late May–early September. For more details on Naumkeag and for the latest dates and tour details, visit the Trustees’ website: https://thetrustees.org/place/naumkeag/.

About The Trustees

The Trustees is a Massachusetts nonprofit that manages over 120 special places across the state, including historic homes, gardens, farms, beaches, and hiking trails. It's the nation's first land conservation nonprofit, founded in 1891. The Trustees offer annual memberships which get you perks across the properties including early access to purchase tickets for events like the Incredible Naumkeag Pumpkin Show, free parking at trails, or discounted (or free) admission to properties. If you visit Trustees properties often or are looking to start exploring more, I recommend a membership. I have been a member for several years now and get so much use out of it.

And now on to the show!…

The Incredible Naumkeag Pumpkin Show

This annual event features over 1,500 jack-o-lanterns along with hundreds of mums and pumpkins. The pumpkins are all hand-carved by Trustees staff and volunteers at Naumkeag and the designs are really creative.

On your visit, you’ll follow the outdoor path lined with pumpkins and Halloween displays. You'll find pumpkins throughout the property, and the displays change each year.

Past years’ events have featured displays including a Jurassic section of dinosaur themed carvings and volcanoes, Harry Potter themed pumpkin displays, and a Hokus Pokus display with glowing green steam rising from a giant cauldron.

One of my favorite parts of the show is walking through the pumpkin tree displays - that’s right, pumpkins are even decorating the tree branches!

And there is even a decorated greenhouse to explore.

Along the way, you’ll also find two cute snack stands where you can pick up a tasty treat, like a cider donut and fresh apple cider. There is usually a cozy fire too where you can stop and enjoy the evening.

After continuing along the path, you’ll make your way up to the mansion where you can explore the first floor of the home. The rooms are even decorated for the season and feature many of the Choate family’s original furnishings.

Planning your visit

When: The event runs each year in October, from Wednesday-Sunday. Hours are generally 5-9 pm with lower capacity early hour tickets available from 4-5 pm. Exact dates and hours may change each year; for the most current dates and times, visit thetrustees.org/halloween.

Tickets: This is a timed-entry event and tickets are sold online in advance only. Tickets typically go on sale to Trustees members first in early September, then to the general public shortly after. The event often sells out so I recommend purchasing your tickets as early as possible to get your preferred date and time.

My tip - Book a sunset time slot. The event is so much fun no matter what time you arrive, but my personal favorite is booking a timed entry that allows you to see sunset. Sunsets can be pretty spectacular here and you’ll have a chance to take in the beautiful Berkshire mountain views all along the way. I usually book a ticket around 6 pm.

Parking: Parking is located off-site and guests can take a convenient short shuttle ride from downtown Stockbridge to Naumkeag. Make sure to plan in a little extra time for parking and the shuttle.

What to wear: The event goes along an outdoor walking path which includes stairs, a steep hillside, and uneven footing at times. I recommend wearing sneakers, boots, or sturdy shoes for navigating the walkways. I also recommend wearing layers as the temperature can drop after sunset. I like to pack a couple different jackets and then decide what I need once I reach the parking lot.

If you're planning a fall trip to the Berkshires, I highly recommend adding this event to your fall trip itinerary. And if you can’t make it this fall, there are plenty of other ways to experience the property throughout the year. Naumkeag is one of my absolute favorite places to visit in the Berkshires year-round.

Winter: Winter Lights, advance timed-entry tickets required, November–January.
Spring: Daffodil and Tulip Festival, advance timed-entry tickets required, April–May.
Summer: General admission is available, and you can explore the gardens in full bloom and tour the first and second floors of the home, typically from May–September.
Fall: The Incredible Naumkeag Pumpkin Show, advance timed-entry tickets required, October.