Your Fall Festival & Event Guide

The Berkshires come alive with farm fun, fright nights, art, music, and much more. Mark your calendar so you don’t miss a thing.

By Amy Krzanik
Photo above courtesy of Felix Carroll & Berkshire Botanical Garden


FESTIVALS AND EVENTS


FALL FOLIAGE & HALLOWEEN TRAIN RIDES
Adams | Through October 26
Hop aboard the Hoosac Valley Train and take a family-friendly journey from Adams to North Adams and back while leaf-peeping, trick-or-treating, and learning about local history.
berkshiretrains.org

TURNPARK FAIR HOUSES FESTIVAL
West Stockbridge | October 11
Immerse yourself in a fairytale atmosphere with twinkling lights, hands-on activities, live performances and delightful food and drinks. Want to submit your own handmade Fairy House? Entries are due October 2-5; see site for details.
turnpark.com

OKTOBERFEST AT BOUSQUET
Pittsfield | October 4
Sample more than 24 craft beers and ciders with your commemorative glass, savor delicious food, and enjoy live music with the best view in the Berkshires.
bousquetmountain.com

BERKSHIRE BOTANICAL GARDEN HARVEST FESTIVAL
Stockbridge | October 11-12
This popular annual event transforms the 24-acre property into a family-friendly celebration of all things autumn. Enjoy a botanical bakery serving sweet and savory treats, a beer garden, food trucks, games, more than 80 craft vendors, a huge plant sale, live music, and more.
berkshirebotanical.org

CONNECTICUT GARLIC & HARVEST FESTIVAL
Bethlehem, CT | October 11-12
It’s the 20th anniversary of this fest celebrating all things garlic at the Bethlehem Fairgrounds. Learn how to grow and cook garlic, enjoy live music, kids’ activities, and crafts, and don’t miss the garlic-themed food court.
garlicfestct.com

HAWTHORNE VALLEY HARVEST FESTIVAL
Ghent, NY | October 11
This free event is held annually to celebrate agriculture, ecology, education, art, and community. Enjoy live music, local vendors and artisans, and organic food, plus hay and horse rides, children’s activities, cider pressing, and more!
hawthornevalley.org

RAMBLE WEEKEND
Adams | October 11-13
This year’s RambleFest party on Saturday (rain date: Sunday) will include live music, food trucks, a beer tent, and tons of craft vendors. Monday’s Ramble is your chance to hike the tallest mountain in Massachusetts, Mt. Greylock, and receive a certificate at the top to prove it.
exploreadams.com/ramblefest

SHAKER SUPPERS
Pittsfield | October 16 & November 29
Suppers include a presentation from an expert interpreter of the Shakers and a communal, Shaker-inspired meal featuring meat and produce from the farm prepared by a local chef.
hancockshakervillage.org

FILMCOLUMBIA
Chatham, NY | October 17-26
Happy 25th anniversary to this festival! Over 10 days, the fest screens the best upcoming American and international films at Chatham’s historic, and newly refurbished, Crandell Theatre. Stay tuned for the last-minute announcement of Saturday night’s Sneak Preview film.
crandelltheatre.org/filmcolumbia

ROOTED IN PLACE
Stockbridge | November 9
Berkshire Botanical Garden’s ecological symposium is an immersive day-long gathering, this year featuring horticulturalist and author Abra Lee giving the keynote speech “Cultivating the Untold Stories of Black Gardeners and Growers.”
berkshirebotanical.org

WANDERING DANCE FESTIVAL
Pittsfield | November 9-15
Wandering Dance returns to downtown Pittsfield for a week-long celebration of movement, creativity, and community, culminating in a dynamic showcase performance at The Colonial Theatre.
milltownfoundation.org/wanderingdance-festival

FARMS


WOODLIFE OKTOBERFEST
New Lebanon, NY | October 11
Stop by for food, brews, and music!
woodlifefarmmarket.com

SAMASCOTT’S GARDEN MARKET & CORN MAZE
Kinderhook, NY | Through October
Each fall, Samascott’s offers a newly designed, 7-acre corn maze in which visitors can get lost. Find the eight hidden items while you’re in there and win a prize! After all that walking, you’ll want to grab apple cider, donuts, and ice cream for the road.
samascott.com

WHITNEY’S FARM MARKET PUMPKIN FEST
Cheshire | Through October 26
Pumpkin Fest returns each September with a haunted corn maze, hay rides, a bouncy house, a petting zoo, and, of course, lots and lots of pumpkins. Stop inside to grab a sandwich or a homemade sweet treat while you’re there.
whitneysfarm.com

IOKA VALLEY FARM
Hancock | Through October 26
Fall weekends mean a trip to Ioka for pumpkin-picking, a kid-sized corn maze, a giant pumpkin house, and more. Have lunch at the Calf-A, serving the farm’s roast beef and maple BBQ sandwiches, snacks, and more, plus desserts to go.
iokavalleyfarm.com


FRIGHTFUL FUN


GHOST TOURS AT THE MOUNT
Lenox | Now-October
Edith Wharton’s former mansion offers a darker (literally and figuratively) guided tour of the house and grounds after sundown, with strange stories, mysterious sounds, and other unsettling phenomena. Family-friendly tours take place earlier in the evening.
edithwharton.org

13 NIGHTS AT JIMINY PEAK
Hancock | September 26-October 31
The terror on the mountain returns with 13 nights of spooky tours and nighttime Mountain Coaster rides for the brave.
13nightsatjiminy.com

THE INCREDIBLE NAUMKEAG PUMPKIN SHOW
Stockbridge | October 1-31
Naumkeag’s wildly popular Halloween extravaganza is always a hot ticket, so make your reservation soon. The show features more than 1,500 carved and illuminated pumpkins set in autumn vignettes around the property.
thetrustees.org/place/naumkeag

PRIDEOWEEN
Dalton | October 10
Berkshire Pride brings back an evening of spooky fun at The Stationery Factory with DJ BFG. This annual celebration brings the queer and trans community and allies together for a night of dancing, costumes, and connection.
berkshirepride.org

HALLOWEEN AT HANCOCK SHAKER VILLAGE
Pittsfield | October 17-30
Nighttime Haunted Hancock walking tours return, with special kids’ tours scheduled for October 18 and 25, and an all-day Halloween Pumpkin Extravaganza with trick-or-treating and pumpkin decorating on October 18.
hancockshakervillage.org

BOOSQUET HALLOWEEN BASH
Pittsfield | October 25
The 2nd annual bash offers a spooky good time that includes live music, a costume contest, a photo booth, snacks, and surprises.
bousquetmountain.com

SPOOKY TRICKS FAMILY DAY
Stockbridge | October 25
The Norman Rockwell Museum invites you to explore the mysteries and visual tricks hidden in the artwork of Walter Wick and Norman Rockwell on a guided gallery walk. Create your own spooky scene in the classroom, and follow an outdoor trail of curious clues that might lead to a surprise treat!
nrm.org

TRICK OR TREAT IN THE PARK AT ART OMI
Ghent, NY | October 25
Goblins, ghosts, and ghouls of all ages are invited to come in costume and enjoy an afternoon of free Halloween fun among the site’s eye-catching outdoor sculptural and architectural works.
artomi.org

DÍA DE LOS MUERTOS
North Adams | November 1
Celebrate Day of the Dead, the Mexican holiday of remembrance for those who have passed away with free admission to Vincent Valdez’s “Just a Dream…” The party continues under Spencer Finch’s “Cosmic Latte,” where you can contribute to an altar with your own ofrenda (offering), including photos or tokens of loved ones, and dance to local musicians. Kidspace will be open for art-making in the spirit of life and death, and a family story time.
massmoca.org


IN THE GALLERIES


BERKSHIRE BOTANICAL GARDEN
Stockbridge | October 18-November 30
“Flock: Watercolor Paintings by Robin Crofut-Brittingham” will feature the paintings from “The Illuminated Book of Birds” (Timber Press), alongside a selection of works from the artist’s ongoing fine art practice.
berkshirebotanical.org

CLARK ART MUSEUM
Williamstown | Ongoing
“Back Bay to the Berkshires: Celebrating 250 Years of Art in Massachusetts” (through November 16) looks at artists and artistic innovations associated with the Bay State, while “Raffaella della Olga: Typescripts” (on view November 22) is the artist’s first solo museum show; she uses typewriters and ink ribbons on a range of materials to make unique artist’s books.
clarkart.edu

HANCOCK SHAKER VILLAGE
Pittsfield | Through November 30
This season’s seven exhibits are up through November 30: Deborah Carter and Joanie Ciolfi’s “Couture from the World,” Maria Molteni’s “All Around the Room,” Kathy Greenwood’s “Elements of Harmony,” Laura Christensen’s “Imagining Shaker Sisters,” Steve Careau’s “Chaste,” Shany Porras’ “Simple Gifts,” and “The City of Peace,” photographs by Dylan Kubis.
hancockshakervillage.org

MASS MOCA
North Adams | Ongoing
Jimena Sarno’s “Rhapsody” (on view October 18) joins the summer debuts “POWER FULL BECAUSE WE’RE DIFFERENT” by Jeffrey Gibson and “Just a Dream…” from Vincent Valdez, plus many, many more long-term works on display.
massmoca.org

NORMAN ROCKWELL MUSEUM
Stockbridge | Starting November 8
Step back into the 1920s and 1930s with “Jazz Age Illustration,” an exhibition exploring the art of popular illustration during this transformative era. Featuring more than 100 works by Aaron Douglas, John Held Jr., and Frank E. Schoonover, the exhibit delves into the cultural impact of illustration during a time of dramatic social change.
nrm.org

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