Check out the events happening this weekend including pumpkin fun, festivals, and spooky nights.
List of harvest festivals and craft fairs here.
Editor's Pick
Photo from Ramblefest 2021
Ramblefest 2025
Adams Visitor Center
Time: Saturday, noon to 5 p.m.
Bring the family and enjoy this free event with live music by Pete Boyd, Project Rewind and more. Also enjoy a variety of food vendors, drinks, and local artisan vendors. The festival precedes the 57th annual Mount Greylock Ramble on Monday.
Westchester Circus Arts offers a live and immersive show inspired by the industrial history of New England. Its all-new show is inspired by the Hoosac Tunnel and the town's first hot air balloon festival. More information here.
Pumpkinfest 2025
Whitney's Farm & Market, Cheshire
Every Friday through Sunday until Halloween
Join the festivities at Whitney's Farm on Route 8 with hay rides, games, glitter tattoos, and more. Kids can venture off into the corn maze or make a new acquaintance at the petting zoo that includes a mini pony, baby goats, sheep, and a peacock.
Children can also scale different structures in the play yard and once they have worked up an appetite, pick up lunch in the farm market. Whitney's is located at 1775 South State Road in Cheshire and is open from 9 a.m. to 6 p.m. daily. More information here.
Harvest Festival
Berkshire Botanical Garden, Stockbridge
Oct 11 and 12
Berkshire Botanical Garden is hosting its annual Harvest Festival this weekend, continuing its beloved tradition that started in 1934.
The garden, located at 5 West Stockbridge Road, will be hosting festivities including family entertainment, a tag sale, a plant sale, a farmers market, and more.
Children can enjoy hay and pony rides, be spooked in a haunted house, or participate in the various other events.
Tickets are $15 and children 12 and under are free. More information here.
13 Nights Returns
Jiminy Peak Mountain Resort, Hancock
The terrifying favorite returns to provide a fright-filled weekend to participants brave enough to enter the haunted house.
Take a group of friends to participate in "13 Nights at Jiminy" every Friday through Sunday from 6:30 until 10:30 p.m. through the month of October.
The age recommendation is 10 and older. Tickets are $29.
You can also ride through the darkness with the resort's Mountain Coaster for $16; The Scream and Scare Package includes one trip through "13 Nights" and two rides on the coaster for $49.
The Christiansen's Tavern will be open to purchase drinks, dinner, or a snack Friday and Saturday.
Gaze at Berkshire County's fall foliage on Berkshire Scenic Railway Museum's Speedliner featuring the two classic Budd Rail diesel cars, New Haven 41 and Baltimore and Ohio 1960.
Tickets range from $13 to $28. More information here.
Naumkeag Pumpkin Show
Naumkeag, Stockbridge
Oct. 1 to 31 on Wednesdays thru Sundays from 5 to 9
More than 1,500 jack-o'-lanterns will grin back at you. Pumpkins, mums, and gourds decorate the mansion's grounds and are sure to be a spectacle the entire family will enjoy. Hot cider and fall treats will be available for sale on-site. Tickets can be purchased here.
Friday
PRIDEOWEEN
Stationary Factory, Dalton
Time: 8 to 11 p.m.
Get ready for a night of drag of some of your favorite musical icons. You’ll be sure to dance the night away. Tickets are $22.
General admission is $22. More information and tickets here.
Saturday
Zombie Pub Crawl
Downtown Pittsfield
Time: 5 to midnight
Unleash your inner zombie while fundraising for Hospice. Wear your most creative undead costume for a chance to win prizes, and gather friends to follow the pub crawl root, starting at Hot Plate Brewing and ending at The Madison at 10 p.m.
There will be live music and a dance party at the Madison, featuring tunes by DJ Pup Daddy.
Sweetwood is hosting its second annual fall festival perfect for a family day outing. Enjoy free admission where you can enjoy local artists, vendors, and eats. There will also be face painting, bounce houses, games, bike raffle, and more. Visitors can also check out a fire truck and police car. More information here.
Tamarack Hollow Berkshire Drum Fest
Windsor Town Hall
Time: 10 a.m.
The 16th annual Tamarack Hollow Berkshire Drum Fest is this weekend featuring multi-level drum, song and cultural classes with Namory Keita, master drummer and cultural ambassador of the Malinke people.
There will also be a community performance featuring Keita, Aimee Gelinas, Tamarack Hollow director, and Dan Cohen with members of Gaia Roots and the Berkshire Rhythm Keepers.
The Lee Farmers Market will be concluding its season with free pumpkin painting. More information here.
Fall Fest
Herman Melville's Arrowhead, Pittsfield
Time: 10 to 4
The Berkshire Museum and the Berkshire County Historical Society is inviting the community to celebrate the fall with a variety of crafts, games, and hands-on activities for children and adults.
The free event features hayrides, lawn games, a cider pressing activity, and more.
For guests over 21, there will be samples of Berkshire Cider Project's hard cider.
The gallery is inviting artists, families, nature lovers, and imaginative builders of all ages to create and submit their own handmade Fairy House for display in its upcoming Fairy House Festival.
The fairy houses will be on display and will enter a juried competition with prizes awarded in multiple categories.
Guests can immerse themselves in a fairytale atmosphere while exploring the sculpture park grounds, wandering among twinkling lights, engaging in hands-on activities, live performances, and food and drinks.
The event will also feature an interactive quest game, meeting and talking with whimsical fairytale characters who will help you gather all the elements and create a brand new fair.
Tickets are $18; kids 3 to 12 are half price. More information here.
Sunday
Phantom of the Opera with Live Soundtrack
Adams Theater
Time: 7 p.m.
Enjoy a live soundtrack by The Invincible Czars to the classic silent film "Phantom of the Opera" for its 100th anniversary. Tickets are $20 for general seating or $35 for priority seating. More information and tickets here.
The Shire Harvest Market
Adams Theater
Time 10 a.m.
Earlier in the day, the theater will be having harvest market to celebrate the bounty of the fall season. The event features face painting, family activities, artisan crafts and vendors, and fall treats. More information here.
Woodcraft Showcase Event
Greylock Glen Outdoor Center, Adams
Time: 10 a.m. to 4 p.m.
Woodworkers, artisans, and makers all across Western Massachusetts will be showcasing their skills with hands-on demonstrations, displays, and more. More information here.
Social Karaoke
Steeple City Social, North Adams
Time: 6 to 9 p.m.
Sing Karaoke and socialize while enjoying the restaurant's regular wines, beers, and cocktails.
Nervous about singing? Ask your hosts to sing alongside you! Newbies and experienced singers alike are welcome. More information here.
Astrology 101 Workshop
Ventfort Hall, Lenox
Time: 11 to 1
In this two-hour lecture, the visitors will learn the basics of astrology so they can read a natal chart.
Tickets for the workshop are $35. Reservations are highly encouraged as seating is limited, with walk-ins accommodated as space allows. More information here.
Join the annual hike up Cheshire Harbor Trail to the state's highest summit. The round trip is 6.6 miles, moderately strenuous and takes about five hours. A shuttle will be making the loop between the Adams Visitors Center, the trailhead and the Greylock Glen Outdoor Center beginning at 8 and ending at 4 p.m. Bascom Lodge will be open for breakfast and lunch from 9 to 3.
Great Barrington
18 Church St.
Saturday: 9 a.m. to 1 p.m., through Nov. 8
The market is open every Saturday. Every week, locally grown food, flowers, and plants will be available, along with other local vendors. The market accepts and offers doubling SNAP, HIP, WIC, and Senior market coupons. More information is here.
Lee
The Town Park
Saturdays: 10 a.m. to 2 p.m., through Oct. 11
The market offers locally grown produce, prepared foods, locally created arts and crafts, and herbal products. YogaLee offers free community yoga from 9:30 to 10:30 on the first Saturday of each month.
The market accepts SNAP, HIP, Senior Coupons, and WIC Coupons and also offers Market Match. More information here.
New Marlborough
Village Green
Sunday: 10 a.m. to 1 p.m., until weather turns
The market has local vendors that offer a variety of goods from produce, eggs, baked goods, jams, hand-knit items, maple syrup, and more. More information here.
North Adams
Main Street
Saturdays: 9 a.m. to 1 p.m., through Oct. 25
The south side of Main Street from American Legion Drive will be closed to make room for the city's weekly farmers market, which will kick off this Saturday. Explore downtown North Adams and discover local businesses and fresh produce from local farms.
Held at Papa's Healthy Food and Fuel with local produce, crafters and performances. More information here.
Pittsfield
Pittsfield Common
Saturday, 9 a.m. to 1 p.m., through Oct. 11
Roots Rising, the region's first teen-run market, will hold an indoor farmers market this Saturday. The event will feature live music, chef demos, workshops, children's activities, and more. More information here.
Sheffield
125 Main St.
Fridays: 3 to 6 p.m., through Oct. 10
The market features healthy food and products from a variety of local vendors, aiming to nourish the community by supporting "local small farms, land, bees, and economy." More information here.
Williamstown
Spring Street
Saturday, 9 a.m. to 1 p.m., through Nov. 1
The market features a diverse range of local food and artisan vendors, along with local services and live music. More information here.
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