Berkshire Magazine Holiday 2025 | Page 14

Historic Houses All Dressed Up
Winterland in Lenox is a heartwarming way to get in the holiday spirit, starting Dec. 5 at 6 p. m. with the Lenox Tree Lighting in Lilac Park, complete with caroling by the Lenox Community Choir and a photo op with Santa. Dec. 6 features Winter Market Shop, Sip & Savor at downtown stores and galleries, 12 to 4 p. m., and ice skating at the Community Center. Details can be found at lenox. org.
The 42nd Williamstown Annual Holiday Walk includes old-fashioned caroling, horse-drawn carriage rides, tree lighting, soup-tasting competition, and the muchanticipated Reindog Parade and visits with Santa! Dog owners are welcome to deck the hounds and join the fun. Dec. 5 – 7. Details are at destinationwilliamstown. org.
Fan favorite alert! Breakfast with Santa on Dec. 6 – 7, 8 a. m. to 12 p. m. at Ioka Valley Farm, 3475 Hancock Rd., a family farm in Hancock since 1936. If you look forward to local maple syrup and cutting down your own Christmas tree, this is the place. Details can be found at iokavalleyfarm. com.
Stockbridge Main Street at Christmas & Norman Rockwell Holiday Celebration is not to be missed! Things kick off on Friday, Dec. 5, at 5 p. m. with“ The Nutcracker Seedling” by Olga Dunn Dance Company at the Stockbridge Library on Main Street, with additional performances Saturday, Dec. 6, at 2 and 3 p. m. On Dec. 6 and 7, the town transforms into a magical place, with twinkling lights and holiday greenery that pay homage to American painter and Stockbridge’ s own Norman Rockwell. Historic property tours of Merwin House and Ventfort Hall happen on Saturday, Dec. 6, 11 a. m. to 3 p. m., and the Albany Pro Musica Chamber Singers perform at the First Congregational Church that evening. On Sunday, Stockbridge comes alive with the 36th reenactment of Norman Rockwell ' s iconic 1967 painting, Home for Christmas( Stockbridge Main Street at Christmas), when Main Street is closed to traffic and 25 vintage automobiles line the street, with a huge Christmas tree standing guard from Rockwell ' s former second floor Main Street studio. Festivities include Victorian Carolers, local high school student singers, horse-drawn rides, children ' s crafts, and visits with Santa. Purchase tickets at stockbridgechamber. org.
Downtown Festive Frolic in Pittsfield launches with the city’ s Park Square Tree
Lighting Ceremony on Dec. 5 at 6 p. m. Saturday events on Dec. 6 include The Berkshire Bazaar( see“ Markets” above); the Wreath Art Auction at the Lichtenstein Center for the Arts at 4 p. m. with a live auction at 5:30 p. m.; Children ' s Paint & Sip at St. Stephen ' s Episcopal Church, 67 East St., 12:30 to 3 p. m.; and photo ops with Santa in Dunham Mall.
The Berkshire Carousel, 50 Center St. in Pittsfield, is open this holiday season, with special treats on certain days. On Nov. 28 and 29, get a gift and shop the vendors on site. On Dec. 6 and 7, enjoy holiday decorations and a chance to win a gift. And you’ ll have one more chance to take a ride on the carousel before the end of the year on Dec. 26 and 27. The Berkshire Carousel is open from 12 to 5 p. m. on all of those days. Tickets are $ 2 and can be purchased at the carousel.
Stockbridge Main Street( Courtesy of Stockbridge Chamber of Commerce)
Great Barrington Holiday Stroll takes over downtown on Dec. 13. Mason Library Hour and Aston Magna Family Performance at Saint James Place begin at 3 p. m. At 4 p. m., the Mahaiwe screens Mickey’ s Christmas Carol on a 30-minute loop. Look for the Character Parade with Santa at 4:30 p. m. at the base of Railroad Street, and then hop on the hayride, which runs until 7:30 p. m. Whether you’ re strolling or riding around downtown, you’ ll see face painting, wreath making, gingerbread house decorating, ice sculpting, live window displays, holiday selfie booth, grab-and-go food, and unique shopping options. Olga Dunn’ s Nutcracker Seedlings perform at 5 p. m. at Saint James Place, Berkshire Hills Chorus punctuate downtown, and Villancicos performs at the top of Railroad Street. Parade of Lights strolls down Main Street to Town Hall, where a menorah, kinara, and Christmas tree will be lit. Fireworks light up the sky at 7:15 p. m., and the evening ends with Songs of the Season by Vocalis Youth Choir at Saint James Place. A detailed schedule can be found at southernberkshirechamber. com.
Holiday Train Rides are a great way to sit back, enjoy the scenery and meet Santa! Berkshire Scenic Railway Museum’ s Tinseliner, a 1950-style stainless steel diesel car, runs Nov. 29 and 30, and Dec. 6, 7, and 13. The Mrs. Claus Cookie Express is one day only, Dec. 20, where all riders get a warm cookie! Trains leave from Hoosac Street in Adams for the hour-long ride. For tickets and times, go to berkshiretrains. org.
The Festival of Trees that started at the Berkshire Museum in 1985 is being held this year at Hancock Shaker Village while the museum is under renovation. Dozens of trees decorated by local organizations, businesses, and individuals inspired by this year’ s theme“ Barn to be Wild” honor the village’ s farm and agriculture heritage. They will be displayed in the historic Round Barn and Poultry House, Fri., Sat., Sun., Nov. 21 – Dec. 28( closed Dec. 25 and 26), 11 a. m. to 4 p. m. Tickets at hancockshakervillage. org.

Historic Houses All Dressed Up

It’ s true. Other parts of the country have holiday markets and outdoor celebrations, but there is nothing like holiday dress-up at the historic castles and cottages that punctuate our Berkshire hills and valleys. These extraordinary properties go out of their way to blend history with contemporary. From house tours to holiday shows, from teas to talks, there is something for everyone!
Talks and Tea with Berkshire-based Authors at Arrowhead will be held at Herman Melville’ s home in Pittsfield, a wonderful way to celebrate the history and culture of the Berkshires. The 2 p. m. readings take place in Melville’ s study, including Nov. 23 by American historian and biographer Debby Applegate; Dec. 7 by award-winning author Michelle Young; and Dec. 14 by longtime columnist and former writer-in-residence at Arrowhead, Kevin O’ Hara. Following the readings, guests can mingle with
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