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Weekend Outlook: Halloween Events, Ramblefest, and More

By Sabrina DammsiBerkshires Staff
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There are a variety of events this weekend, including Halloween-themed events, Ramblefest, live music, and more. 
 
See a list of Farmer's Markets here.
 
Editor's Pick
 
Purgatory Road Jr. 
190 Cleveland Road, Dalton
Oct. 12, 13, 19 and 20 from 4 to 7 p.m.
 
Although the annual Purgatory Road event is not taking place this year, there is still an opportunity to support the Berkshire Coalition for Suicide Prevention. This year, however, the event is kid-friendly. 
 
According to a Facebook post from the organization, the haunted house will return in 2025. This year, the event is designed with younger kids in mind and is not scary. 
 
It will include a path through a cornfield that should take about 15 to 20 minutes to walk through. As you stroll through the maze, you will be accompanied by Halloween music and decorations. There will also be the possibility of encountering some carnival characters.
 
The maze will also include games and obstacles for children between the ages of 3 and 8. During the games, children can win tickets and exchange them for prizes at the end. 
 
Face painting is offered to all ages. Food and balloons will be available for purchase. Tickets cost $10 for children ages 3 to 8 and $5 for adults and older children. 
 
More information here
 
Friday 
 
Prideoween
The Stationery Factory, Dalton
Time: 6  to 11 p.m. 
 
Celebrate identities and foster community connection, welcoming everyone regardless of identity with this Halloween LGBTQIA-plus pride event. 
 
The event includes a costume contest with prizes, a drag show featuring local Queens, access to community resources from partners like Berkshire Harm Reduction and Tapestry Health, and shopping opportunities for witchy goods and Pride gear. 
 
Tickets range from $15 to $50. More information here
 
Samirah Evans Performance
The Colonial Theatre, Pittsfield 
Time: 7:30 p.m. 
 
Jazz and blues vocalist Samirah Evans will be performing her dynamic New Orleans flavor. 
 
She has performed at various venues and festivals, released an album, and advocates for indigenous American music. Currently, she is an Artist Associate in Jazz Voice at Williams College. 
 
Tickets cost $30. More information here.
 
Greylock Glen Outdoor Center Grand Opening
Gould Road, Adams
Time: 11 a.m. 
 
The long-awaited center is opening this Friday with a ribbon cutting. The outdoor center will consist of retail and education wings, a food service area, space for support services, and an outdoor pavilion. 
 
More information here
 
Saturday 
 
Springfield's Gilded Age Walk 
Springfield Museums, Springfield
Time: 10 a.m. to Noon
 
Springfield Preservation Trust will host a walk around downtown Springfield to explore the city's legacy during the Gilded Age, America’s most prosperous period.
 
This tour, guided by Westfield Athenaeum Executive Director Guy McLain, will feature art and architecture from across Springfield’s metropolitan landscape.
 
Tickets range from $5 to $10. More information here.
 
Kids Paint and Sip
Artsy Avenue, North Adams
Time: 6 p.m. 
 
There will be Halloween painting for the kids. If your child is under the age of 8, attend with them. Send a message to the venue register. More information is here
 
DIY Cauldron Candle Workshop
20 Williamstown Road, Lanesborough
Time: Noon 
 
Join the Lanesborough Local Country Store to create a cauldron candle. 
 
Jenna from Berkshire Candle will provide the scents and wax. The ticket includes treats and a spooky-themed drink.
 
Tickets are $50. More information here
 
Two Piano Journey Benefit Concert
The Adams Theater 
Time: 4:30 p.m. 
 
Two Piano Journey is returning to The Adams Theater to perform a benefit concert in support of the launch of the 2025 Annual Fund. All proceeds will go towards planning for the theater’s 2025 season 2025.
 
Tickets range from $22.25  to $102.25, including fees. More information here
 
Bingo and Brew
Hot Plate Brewing Co., Pittsfield
Time: 4 to 8 p.m. 
 
The brewery will be hosting bingo and raffles. There will also be food from Flavorful Bites Food Truck. More information here
 
Maple Street Cemetery Tour
Maple Street, Adams
Time: 5:30 to 6:30 p.m.
 
The Adams Historical Society offers a tour of the historic cemetery with costumed presenters of some of the town's past notable figures. Meet at the Maple Street entrance, tour ends at the Quaker Meetinghouse. Walk includes up and down hills. Rain location is the GAR Hall at the Adams Free Library. 
 
More information here.
 
Sunday 
 
Ramblefest
Adams Visitors Center
Time: noon to 5 p.m. 
 
Ramblefest, a party to complement the annual Mount Greylock Ramble, is taking place this weekend and will feature live music, food, activities, and more. 
 
The event features food and drinks from local restaurants and organizations, including Bezzle's BBQ, Pizza House, Tres Ninos, Adams Lions Club, Antimony Brewing, Two Roads, Shipyard, and more.
 
More information here
 
Fall Bazaar/Kids' Fair
Maple Street, Adams
Time: 9 to 4
 
The Parish of St. John Paul II in Adams is hosting its annual fair in the former Notre Dame School building on Maple Street. 
 
It includes a chinese auction, baked goods, four shops — Christmas, fall, handmade and country store — and the kitchen offers hamburgers & hotdogs, sweet sausage grinders, French meat pie, corn chowder, and an array of Polish foods. Also jewelry, silent auction, books and CDs, and raffles, and kids' fair with games and prizes. 
 
Tarot Card Reading Workshop
Ventfort Hall Mansion, Lenox
Time: 2 to 4 p.m. 
 
The workshop will cover how to formulate meaningful queries and explore Tarot spreads. 
 
The workshop costs $45, and reservations are highly encouraged due to limited seating. Walk-ins will be accommodated as space allows. 
 
More information here
 
Sensing Nature: From the Outside In
Clark Art Institute, Williamstown
Time: 2 p.m.
 
A Clark educator will lead a new seasonal program at the museum, focused on connecting visitors with nature and art to enhance their wellbeing. 
The program includes a mindful walk in the woods to engage the senses with the natural environment, followed by a contemplative art-looking experience in the galleries.
 
The event is free. Advance registration required. More information here
 
 
Multiple Days
 
The Mill Town Circus
Noel Field, North Adams 
Oct. 4th through Oct. 14 
 
The circus has come to the Berkshires. The show promises to captivate audiences with its mix of historical storytelling and circus performances. The show will showcase acrobatics, aerial acts, and stunts against a backdrop reminiscent of the city's industrial history. 
 
Tickets are $15 for general admission or $25 for front-row seats. More information here
 
 
Ashfield Fall Festival 
Town Common
Time: Oct. 12-13, 10 to 5
 
Annual craft fair and festival. Plenty of vendors with handmade items, jewelry, apparel, word working, prints and paintings, textiles, books and stained glass. Plus local produce, herbal goods, maple products, jellies and fruits, and games and entertainment. Food and beverages available, including maple cream fried dough, homemade pies, fudge, chowder, ice cream, doughnuts and more. 
 
More information here
 
Fall Foliage Train Rides 
Hoosac Valley Train Ride, Adams
 
Gaze at Berkshire County's fall foliage on Berkshire Scenic Railway Museum hour-long train ride on its fully restored, 100-hundred-year-old coaches. 
 
The rides will take place Saturday and Sunday at 11, 1:30, and 3 p.m. Tickets range from $13 to $24. More information here
 
Whitney's Farm Pumpkin Fest
Whitney's Farm, Cheshire
Sept. 23 until Oct. 29 – Friday, 2 to 5:30 p.m., Saturday and Sunday, 11 a.m. to 5:30 p.m. 
 
Pick pumpkins, ride on a hay wagon, get glitter tattoos, walk through a corn maze, and more every weekend through Halloween. 
 
The event also features a new scarecrow shooting gallery, a giant slide, jumpin' pumpkin, a bounce house pumpkin, and a new playground. 
 
More information here
 
Connecticut Renaissance Faire
Lebanon (Conn.) Country Fairgrounds, 122 Mack Road
Time: weekends from Sept. 21 to Oct. 20, 10:30 to 6
 
The 26th annual fair features armored combat, jousting, demonstrations, marketplace, feasting, performances and music. Admission $10 to $16, children 6 and younger free. 
 
More information here

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Fenton: Governor's Council Must Deliver for the Berkshires

Community submissionGuest Column
I am a Springfield lawyer running for Governor's Council and I am asking for Berkshire County residents to support me over an incumbent from North Adams. 
 
Here's why: Last year I learned about staffing issues in our regional courts that I could not ignore. In 2025, it was reported that four of Western Massachusetts' 11 Superior Court judgeships were vacant, all at the same time. A few weeks later, that grew to five vacancies. This meant there were only six Superior Court judges serving all of Western Mass at a time when Berkshire, Hampshire, Franklin, and Hampden counties had more than 100 pending homicide cases. 
 
Those numbers were alarming to me, so I started to engage with leaders in the community who work most closely with the court system and I came to learn that these vacancies were only the tip of the iceberg here in Berkshire County.
 
I learned that no Superior Court or District Court judge had been appointed from the Berkshires since the current incumbent took office. As a result, there is not a single Superior Court judge who lives in the Berkshires today, and several of the District Court judges drive in from other counties to support Berkshire courts in Pittsfield, Great Barrington, and North Adams. Court staff also informed me about severe staffing shortages at the Berkshire Clerk of Courts office resulting in other counties needing to loan staff to the Berkshires just so hardworking employees can take a brief and planned summer vacation. This is not normal. These issues are a reflection of genuine problems with the Berkshire County court system and show a lack of proactive attention from our Governor's Councilor.
 
Instead of focusing on regional equity, I watched as the current incumbent celebrated that she has voted against the governor's nominees more than any other councilor, without much explanation as to why. Most recently, she voted against two extremely qualified former prosecutors for the Parole Board. This was despite an in-person plea from the governor and a letter of support from all the three of the district attorney's from Western Mass. Those votes do not show independence or standing up for principles, they demonstrate naivete, and an unwillingness to work with the key stakeholders.
 
I had seen and heard enough. I decided to jump in the race and challenge the incumbent to address these problems head-on.
 
I am a partner of a regional law firm. I understand our courts and the importance of having qualified, fair and hardworking judges. And I know how important it is to have judges from the Berkshires serving the Berkshires. To achieve that, you need strong relationships with the legal community and local stakeholders. You need to know how to use the power of the Governor's Council to fight forcefully for our region. And you need to be laser focused on identifying vacancies before they occur so that they can be filled quickly with local candidates.
 
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