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Weekend Outlook: Country Fairs, Pumpkin Fests, Latino Celebrations

By Sabrina DammsiBerkshires Staff
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There are a variety of events this weekend, including a country fair, live music, and more. 
 
See a list of Farmer's Markets here.
 
Editor's Pick 
 
Country Fair 
Hancock Shaker Village
Sept. 28 and 29, 10 a.m. to 5 p.m. 
 
The village is hosting its annual county fair, which will feature live music, horse-drawn carriage rides, workshops, demonstrations, an antique quilt show, a farmer's market, an antique car show, a timber framing workshop, face painting, and craft vendors. 
 
There will also be freshly made cider donuts and other treats from Great Cape Bakery, grilled food from Woodlife Kitchen, and craft beer, bourbon, and cider tastings from Bright Ideas Brewing, Berkshire Mountain Distillers, and Berkshire Cider Project.
 
More information here
 
Multiple Days 
 
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
 
The Big E
Eastern States Exposition, Springfield
Time: Sept. 13 to 29
 
New England's biggest fair runs through the end of the month. The fair features goods from all six New England states, specialty days, crafts, demonstrations, activities, agriculture, horse shows, and more. 
 
Tickets range from $12 to $20 for day passes. Special performances are priced separately. 
 
More information here
 
Friday 
 
The ABOMBS Performance 
Dotties Coffee Lounge, Pittsfield 
Time: 6 to 10 p.m. 
 
Energetic rock and roll ABOMBS will be performing their own twist of classic songs from artist Pink Floyd, CCR, ZZ Top, Steve Miller Band, and more. 
 
More information here
 
Dinner with Your Dog
Dotties Coffee Lounge, Pittsfield
 
Friendly and well-behaved dogs and their family are welcome to have dinner at Dorothy's. Seating is at 5:30 pm on the patio, inside, in case of inclement weather. A three-course meal for you and your pup is $30, $20 per additional human, and $10 per additional dog. Reservations required. 
 
More information here
 
Taylor Swift Glow Night
Ready Set Play, Pittsfield  
Time: 5 p.m.
 
Sing along to Taylor Swift songs and play in the indoor playground's glow lights. The first 50 kids will get a Taylor Swift gift. More information here
 
Saturday 
 
Greylock Go Around 50K Mountain Bike Fundraiser
Greylock Glen, Adams
Time: 7 p.m. 
 
There will be a 30-mile mountain bike ride fundraiser for the Thunderbolt Ski Runners. 
 
The ride circumnavigates Mount Greylock, starting at Greylock Glen. Funds raised will help maintain and grow the mountain bike and ski trail around the base of Mount Greylock.
 
There are three aid stations along the course and a post-event gathering that includes burritos, beer, and a raffle. 
 
Fees range from $50 to $75. More information here.
 
Clarksburg Townwide Tag Sale
Time: 9 to 2
 
The Clarksburg Historical Commission is hosting its second annual townwide tag sale and fund raiser. Stop by Town Hall on Saturday to browse the offerings and pick up a list of tag sales around town. 
 
Festival Latino
Green Park, Great Barrington
Time: noon to 6
 
Held at the Green Park and Saint James Place to celebrate the colors, flavors, and sounds of Latin America. Includes dance performances, Latin cuisine, artisan crafts, live music and Djs, local organizations and resources. 
 
Free and family friendly. More information here
 
Harvest & Rustz: A Neil Young Experience
The Stationery Factory, Dalton 
Time: 8 p.m. 
 
Western Mass-based band Harvest and Rust will reproduce every era of Neil Young's music. Tickets are $27.38. More information here.  
 
Summit Chairlift Rides
Bousquet, Pittsfield
Time: 11 a.m. to 2:30 p.m. 
 
Take a scenic ride to the top of Bousquet Mountain and soak up the fall foliage from a new high. Tickets are $12. More information here
 
Corvettes Show
Sugar Hill Assisted Living Community, Dalton
Time: 10 to 2 p.m. 
 
Several Corvettes will be on view. The show will also feature food, raffles, and live music. The car entry fee is $25, which includes a free lunch for two. 
 
More information here
 
Fall Festival
St. Paul's Episcopal Church, Holyoke
Time: 9 to 3 p.m. 
 
The festival will feature vendors, lunch cafe, bake sale, plant sale, scarecrow making, raffles, and more.
 
More information here
 
Becket Family Fun Festival
Town Pavilion
Time: noon to 9, rain or shine
 
The Becket Parks and Recreation Committee presents the first Fall Family Fun Festival with music, food, games, a farmers market, and a tag sale at the pavilion on Main Street between Town Hall and the Country Store. The event is free of charge. Games will include volleyball, kickball, and pickleball during the day, bean-bag baseball and Wiffle ball in the evening. A barbecue will supplement the fare for sale by The Country Store and music starts at 2 p.m. 
 
Tag sale participation $5; more information here
 
Sunday 
 
Poets Creating Conversation
The Mount, Lenox 
Time: 1 p.m.
 
WordXWord invites poets to attend the event and share their work that aligns with the theme “Between.”
 
WordXWord events are free and open to all. However, some poems may contain content or language best suited for teens and adults.
 
More information here
 
Chester and Becket Railroad Tour
52 Hampden St, Chester
Time: 1 p.m.
 
There will be a hike on a section of the Chester and Becket Railroad. The railroad was built in 1896 as a 5.25-mile spur off the Boston and Albany Railroad to deliver granite from the Becket Quarries to the Chester finishing works. 
 
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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