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Looking for a fall getaway filled with glowing pumpkins, colorful foliage, historic haunts, and classic New England charm? The Berkshires are an ideal Halloween destination, with scenic mountain landscapes, welcoming small towns, and seasonal attractions throughout the region. From an illuminated Gilded Age estate to apple picking and haunted adventures, this weekend Halloween itinerary in the Berkshires, MA, will help you plan a memorable Friday-through-Sunday escape.
Friday Evening: Pumpkins and Ghost Stories
See the Naumkeag Pumpkin Show
Start Friday evening at the Naumkeag Pumpkin Show in Stockbridge. This historic Gilded Age estate transforms its gardens with glowing jack-o’-lanterns and festive fall displays. The evening setting makes it a beautiful first stop for enjoying both the Halloween atmosphere and Berkshire history.
The show typically runs on select fall evenings, so check current dates and purchase tickets in advance before visiting.
Take a Ghost Tour at Ventfort Hall
Continue to Lenox and Ventfort Hall Mansion and Gilded Age Museum. Built in the 1890s, this impressive mansion offers a glimpse into the Berkshires’ Gilded Age past.
During the Halloween season, ghost tours share stories of unexplained happenings and reported encounters inside the mansion. Check the current schedule, as seasonal tours may be offered only on specific dates.
Saturday: Orchards, Markets, and Halloween Thrills
Start at Bartlett’s Orchard
Spend Saturday morning at Bartlett’s Orchard in Richmond. Depending on the season, visitors can pick apples or browse the farm market for fresh cider, cider donuts, baked goods, and other fall favorites. Check picking conditions before visiting because apple availability changes throughout October.
Explore the All Hallows Lee Market
In the afternoon, head to Lee for the All Hallows Lee market. This seasonal gathering brings together local artisans, small businesses, and vendors, making it a fun opportunity to shop locally while exploring one of the Berkshires’ inviting towns.
Experience 13 Nights at Jiminy Peak
Saturday evening brings the biggest scares on this weekend Halloween itinerary in the Berkshires, MA. Head to Jiminy Peak in Hancock for 13 Nights, a nighttime haunted attraction recommended for ages 10 and older. For 2026, the event runs on select October evenings from 6:30 to 10:30 p.m. Visitors can also add an after-dark ride on the Mountain Coaster, which reaches speeds of up to 23 mph.
End the Night at Doctor Sax House
For a late-night Halloween experience, head to Doctor Sax House in Lenox. The venue hosted Death X Disco on Halloween night in 2025, featuring DJs, costumes, dancing, tarot readings, and Halloween-inspired cocktails. Because programming changes each year, check the current calendar to see whether Death X Disco or another Halloween event is scheduled during your visit.
Sunday: Foliage and Berkshire Art
Walk the Ashuwillticook Rail Trail
Slow down Sunday morning with a walk along the Ashuwillticook Rail Trail. Following a former railroad corridor through the Hoosac River Valley, the paved trail offers views of waterways, mountains, wooded landscapes, and brilliant autumn foliage. Choose a shorter section for an easy morning outing.
Explore the Norman Rockwell Museum
Finish your weekend at the Norman Rockwell Museum in Stockbridge. Along with its celebrated collection of American illustration, the museum offers changing programs and family activities. Check its events calendar for mystery-themed, interactive, or Halloween programming scheduled during your stay.
Plan Your Halloween Escape
A weekend Halloween itinerary in the Berkshires MA, combines spooky attractions with orchards, historic towns, art, and beautiful fall scenery. For more seasonal activities to add to your stay, explore our Pittsfield fall weekend guide.
