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Weekend Outlook: Spooky Pumpkin Fun

By Breanna SteeleiBerkshires Staff
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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.
 
More information here
 
Multiple Days
 
Mill Town Circus
Noel Field, North Adams
From Oct. 3 through 13
 
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.
 
More information and tickets here
 
Fall Foliage Train Rides 
Hoosac Valley Train Ride, Adams
Oct. 11 thru 13; Departure Times: 11:30, 1:30, and 3 p.m. 
 
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. 
 
Crawl Route at times here
 
Sweetwood Fall Festival
1611 Cold Spring Road, Williamstown
Time: 10 a.m. to 3 p.m.
 
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. 
 
More information here
 
Kids' Day Pumpkin Painting
Park Square, Lee
Time: 10 a.m. to noon
 
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. 
 
More information here
 
TurnPark Fairy House Festival 
TurnPark Art Space, West Stockbridge
Time: 4 to 8
 
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
 
Monday
 
Adams Visiter Center, Greylock Glen
Time: 8 a.m.
 
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. 
 
More information here
 
 
Farmers Markets 

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. 
 
More information here
 
Otis
2000 East Otis Road
Saturdays: 9 a.m. to 1 p.m., through Oct. 11
 
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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Friday Front Porch Feature: An Attractive Home With a Pool

By Breanna SteeleiBerkshires Staff

CHESHIRE, Mass. — Looking for a beautiful and updated New England farmhouse with a place to relax in the sun? Then this is the home for you.

Our Friday Front Porch is a weekly feature spotlighting attractive homes for sale in Berkshire County. This week, we are showcasing 53 Depot St.

This home was built in 1860 and has a bedroom on the first floor with the full bath and two bedrooms and a bathroom on the second floor. The kitchen has been completely renovated with granite countertops and stainless steel appliances; the back door leads to a large composite deck and above-ground pool. It also has a wrap-around front porch, detached two-car garage and a pellet stove to keep you warm on those cold Berkshire nights. 

It is 1,756 square feet on a half acre and is listed for $384,900.

We spoke to listing agent Heather King of Alton and Westall Real Estate Agency.

What do you think makes this house stand out in the current market?

King: This property truly stands out for its attractive price point and the many upgrades completed by the sellers. The new owners can simply bring their belongings — everything that could have been done has already been taken care of.

Do you know any unique stories about this home or its history?

The home features unique historical details, including the original dining room mantel and hardwood flooring, both dating back to the home's original construction in 1860. While the seller has chosen to retain the original mantel, a new pellet stove has been installed in the dining room, providing an efficient and attractive supplemental heat source. 

Are there any standout design features and/or recent renovations?

This property has seen numerous updates, including a new septic system installed three years ago. The home features a newly renovated kitchen, along with fully updated plumbing and electrical systems. All windows are brand-new, every room has been freshly painted, and both bathrooms have been completely renovated within the past two years with tasteful, modern finishes. The front wrap-around porch and back decking around the pool has been updated with Trex decking in the last two years. 

What kind of buyer do you see this home being perfect for?

This versatile property can accommodate a wide range of buyers. The first-floor primary suite is ideal for those seeking the convenience of one-level living, while the three-bedroom layout also makes it a great option for a family. Enjoy outdoor living with a beautiful deck and pool — perfect for relaxing and entertaining throughout the summer months.

What would sellers like about the location?

Located in Cheshire, the home benefits from low taxes and convenient access to Route 8. Travel south to enjoy all that South County has to offer, including Tanglewood, numerous theaters, and a wide variety of dining options. Head north to explore Mass MoCA, stroll the historic North Adams Main Street, or visit Williamstown and the renowned Williamstown Theatre Festival.

The property is also just a short walk from the Ashuwillticook Rail Trail, offering easy access to outdoor recreation right in town.

You can find out more about this house on its listing here.

*Front Porch Feature brings you an exclusive to some of the houses listed on our real estate page every week. Here we take a bit of a deeper dive into a certain house for sale and ask questions so you don't have to.

 
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