More than 1,500 hand-carved jack-o'-lanterns light up the gardens of this Gilded Age estate, alongside mums, pumpkins, and gourds, many grown right on the property. Cauldrons, cobwebs, fairy houses, and a volcano round it out, with hot cider and fall treats for sale. Timed tickets must be bought in advance and there are none sold on site. Everyone shuttles in from designated parking, and plan on about an hour on the grounds.

Lenox’s signature fall festival featuring more than 100 artisan and food vendors, live music, family activities, and a full downtown street fair experience. Free to attend, a day of family fun with music, food & kid’s carnival.  Musical performances throughout downtown.

Come check it out!!

A proper country fair on one of the most beautiful properties in the county. Live music, craft workshops and demonstrations, a quilt show and sale in the iconic Round Barn, a farmers market, craft beer and cider, antique tractors, farm animals, and dozens of vendors. There's a pie contest and a chicken race for the kids.

A hands on afternoon with the Abode Apothecary covering how elderberries are dried, tinctured, and cooked down into syrup, with time to walk the fall gardens afterward. Tickets are $35 and the session runs two hours, ending at 4 PM. Wear clothes you do not mind staining, because the berries win every time.

Make the drive up for one of American songwriting's true originals. Three-time Grammy winner Lucinda Williams brings her band to the Hunter Center behind her eighteenth studio album, World's Gone Wrong, a set of urgent, unflinching songs written in a burst of collaborative energy. Time Magazine once called her America's best songwriter, and 45 years into her career she still plays like she has something to prove. Tickets run $59 general admission, $99 preferred.

Author and teacher Robert Oakes leads a day-long storytelling workshop at this interfaith retreat center, where you build and deliver a personal account of something that falls outside the ordinary: a ghost encounter, a strange dream, a vision, a moment you have never quite explained. Tickets run $95 and include campus access plus a 6 PM dinner from the kitchen there, with the afternoon moving between writing time, walks on the old Shaker grounds, feedback rounds and readings. The night ends around a fire, where Oakes tells ghost stories from the Shaker community that once lived on this land and at nearby Hancock Shaker Village.

Dare Bottleshop hands its shop floor over to a mobile raw bar once a month, and the October edition opens the long holiday weekend. Oysters get shucked to order, Maine lobster rolls come out of the same setup, and a complimentary tasting is pouring alongside. Six hours is a generous window, so it works whether you are arriving early or coming back off a trail.

Devendra Banhart, Gyan Riley, and Noah Georgeson bring Hug to the Hunter Center stage. On paper it's a guitar trio, but the record wanders somewhere stranger and warmer than that, weaving folk, ambient, and experimental threads with field recordings and Sanskrit chant. Written and recorded in three weeks, it plays like three old friends thinking out loud together. Tickets are $46 advance, $56 week-of, $76 preferred.

A Berkshire tradition since 1934, spread across 24 acres at peak foliage. Main stage entertainment, a beer garden and botanical bakery, food trucks, a plant sale and tag sale, pony rides and hayrides, and dozens of artisan and craft vendors. Parking is free and ample. Saturday draws the crowds, so come Sunday morning if you want shorter lines and better vendor access.

Two hours at the forge with an instructor, one on one. Registration required and spots are limited. Also offered November 14th if October fills.

Raul Midón turns a single acoustic guitar into a full band, weaving soul, jazz, and Latin rhythms around a signature "mouth trumpet" that sounds like the real thing. The Grammy-nominated singer-songwriter plays two sets in the Indigo Room, the Mahaiwe's converted firehouse space with café-table seating and a bar. A later set follows at 8:30 PM!

NPR called them indie rap's favorite friendship, and they're bringing it to the Hunter Center for one night behind their collaborative album Pompeii // Utility. Earl Sweatshirt has spent over a decade building a catalog of dense, introspective, unmistakably his own records, and MIKE matches him step for step. With support from harrison (SURF GANG) and Anysia Kym. Tickets are $51.50 general admission, $88.50 preferred

One of the best evenings on the Lenox calendar, and it happens right outside your door. The Lenox Community Center and neighboring organizations set up a Trunk-or-Treat, then the whole crowd of costumed littles parades through the Village, stopping at participating businesses along the way. Free, festive, and over by 7:30, which makes it easy to fold into an evening.

The museum stays open late just for families. Wander select exhibitions after hours, catch live music and dance performances, make art, get faces painted, and take on the Museum of Mysteries Quest, working together to hunt down clues in the galleries and earn your own artist kit. Food and giveaways too. Free, with a suggested $5 donation. RSVPs are encouraged but not required.

Russell Lord, the museum's Chief of Curatorial Affairs, digs into Bill Watterson's art and creative process, the history of the comics, and the cartoonists who shaped him, including George Herriman and Charles Schulz. Held before public opening hours, so it's a quiet morning in the galleries. $20 plus admission, $10 for members. Reserve early.