Whitney's Farm Market & Garden Center

1775 South State Road, Cheshire 

Open: Daily from 9 to 6

Let the kids 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 scale different structures in the play yard and once they have worked up an appetite, pick up lunch in the farm market. 

 

Don't miss the center's annual Pumpkin Fest happening every weekend through October, featuring pumpkin picking, hay wagon rides, glitter tattoos, and more. More information here. 

 

Berkshire Botanical Gardens

5 West Stockbridge Road, Stockbridge

Open: Daily from 9 to 5 

 

The 24 acre garden highlights plants that thrive in the Berkshires. Families can explore the "living classroom" and partake in different workshops held throughout the season.

 

The garden closes for the season at the end of October but will host a special Harvest Festival on Oct. 11 and 12. Check out our list of harvest festivals and craft fairs here. 

 

 

 

Hancock Shaker Village

1843 West Housatonic St., Pittsfield,

Open: Daily from 10 to 5 until Nov. 2; Nov. 3 thru 30 open from 11 to 4

 

The Village offers a portal into the past. Visitors can get a glimpse into how the Shakers lived explore trails, and partake in family-friendly activities.

 

The Discovery Barn offers hands-on activities for children. Kids can spin wool, construct a Shaker chair, or weave on a loom. Farm activities include watching baby chicks hatch or milking a life-size replica of a Holstein cow. Kids can also sit in on a 19th-century school lesson in the schoolhouse. 

 

The Village will also be providing families the opportunity to celebrate Halloween with its holiday themed events including Haunted Hancock for Kids and Halloween Pumpkin Extravaganza. 

 

Haunted Hancock for Kids is on Oct. 18 and 25 at 5 p.m. Children between the ages of 8 and 12 will take a 45-minute spooky walk through the Village and visit the Brick Dwelling. There is also an adult only version of Haunted Hancock. 

 

The Halloween Pumpkin Extravaganza, on Oct. 18, invites visitors to wear their costumes, trick-or-treat, meet Valerian the Garden Witch, decorate a pumpkin, and visit the Dwelling kitchen. 

 

Purgatory Road Junior

190 Cleveland Rd, Dalton

Open: Oct. 11, 12, 18, and 19 from noon to 3 p.m.

 

This not-scary child-friendly event helps raise funds to benifit Berkshire Coalition for Suicide Prevention. It features a short hayride, a corn maze, games, and more. Tickets are $10 for children and $5 for adults. More information here. 

 

There is also a scary adult version of Purgatory Road.

 

Clarksburg School's Haunted Hayride

Open: Oct. 18 from 6:30 to 9 p.m. 

 

The event features hay-covered trailers prepped for a ride down a glowing, pumpkin-lined road into the “haunted” camping area, where spooky scenes and decorations await. Tickets are cash only and cost $10 for ages 6 and up and $5 for ages 5 and under. More information here.

 

Ashuwillticook Rail Trail

 

In the fall the trail takes on an entirely new color palette. Bring the entire family along for a meandering walk or a brisk bike ride. Hop on the 12.7-mile converted railroad line anywhere between Adams and Pittsfield. The path officially starts on Lime Street in Adams and terminates in Pittsfield off Route 7.