Above: I’ve created this page to make it easier to track the many holiday events in or related to Southborough that residents may want to mark on their calendars. (photos from past year’s celebrations and sales top L-R by Susan Fitzgerald and Messiah Chorus, bottom by Beth Melo)
I’ve created this page to keep track of the upcoming events related to the winter holidays (and shopping).1 These are mostly events in town. But I also included a few events in nearby towns when they have clear links to Southborough (like regional singing groups that include residents and events related to our regional high schools.)
I’ll be updating it with links to more details as those are posted. I’ll also regularly remove events after they happen to make it easier to find what is still to come.
If you want to look back at the details of past events, you’ll still be able to find the full list here and holiday related stories here. For this week’s events, including ones that don’t relate to the holidays, click here.)
Now through Monday, December 15, 2025
Holiday Decorating Contest & Map registration: Southborough Recreation is encouraging residents to register for a contest and provide info for a community map to enjoy festively decorated homes. For details, click here.
Friday, November 28 & Saturday, November 29, 2025 (and season long)
Black Friday and Small Business Saturday: I encourage residents to make a special effort to support at least one Southborough small businesses on these special shopping days, but also throughout the holidays. Click here for my Shop Local directory. (And for special shop local events, click here.)
SFA Christmas Tree Sales begin (1:00 – 8:00 pm) @ 32 Cordaville Road: The first days of the annual Christmas Tree Sale by Southborough Firefighters. This will continue daily (with differing hours) until they sell out. For details, see related post.
Holiday Ladies Night (6:00 – 8:30 pm) @ Gulbankian Florist, 40 Mt Vickery Rd: There is a fee to attend this event with refreshments, raffles, shopping, and discounts. Proceeds from $5 tickets will be split between the Southborough Food Pantry and the Community Free Fridge. For details, click here.
Friday, December 5, 2025
Girl Scout Holiday Sing-along (6:00 – 7:00 pm) @ Community House Lawn: Free annual event for all families in Southborough. An old-fashioned holiday sing-along with some modern touches. Capped off with hot cocoa and treats. (Participants are encouraged to bring a gift to donate to Project Just Because.)
Saturday, December 6, 2025
Annual Kids Shop (9:00 am – 2:00 pm) @ (new location!) Southborough Senior Center, 9 Cordaville Hall: An annual Southborough tradition. Boy Scout Troop 92 provides a safe haven for kids to do their own holiday shopping. While waiting, adults can enjoy a bake sale and coffee.
Christmas Bazaar (10:00 am – 2:00 pm) @ St. Mark’s Episcopal Church, 27 Main Street: Featuring the White Elephant and craft sales, a silent auction, basket raffle, a lunchtime Café, and more. For details, see dedicated post.
Holiday Tree Party (10:30 am – 3:00 pm) @ Southborough Library: Kids are invited to drop-in to enjoy refreshments and make ornaments to hang on the library holiday tree. Sponsored by the Friends of the Southborough Library.
Holiday Book Sale (11:00 am – 3:00 pm) @ Southborough Library: The Friends of the Southborough Library will be holding a special sale with DVDs, CDs, and more. One free book per child.
St. Anne’s Lessons and Carols (6:00 pm) @ St. Anne’s Church, 20 Boston Rd: The service of Lessons and Carols will take place after the 5:00 pm mass in the main church.
WCC Holiday Show (2:00 pm) @ Gibbons Middle School, Westborough: The Westborough Community Chorus will perform its annual Holiday Show, “Winter in the Woods”. For details, click here.
Sunday, December 7, 2025
Santa Day (10:00 am – 1:00 pm) @ Community House, 28 Main St: Free event for the community. See Santa arrive by helicopter (or fire engine in case of inclement weather). Then join him and Southborough Kindergroup at the Community House for activities and refreshments before kids share their wishes with Santa while posing for a picture. For details, see dedicated post.
DECA The Halls Craft Fair (10:00 am – 1:00 pm) @ Algonquin Regional High School Cafeteria, 79 Bartlett St, Northborough: Fair of local vendors selling only handmade goods. The event is a fundraiser for ARHS’ DECA program. To learn more, click here.
NACC Concert (2:00 pm) @ Algonquin Regional High School Auditorium, 79 Bartlett St, Northborough: 53rd Annual Christmas concert “Songs of the Season”. For details, click here.
WCC Holiday Show (2:00 pm) @ Gibbons Middle School, Westborough: The Westborough Community Chorus will perform its annual Holiday Show, “Winter in the Woods”. For details, click here.
Handel’s Messiah Concert (3:30 pm) @ Pilgrim Congregational Church, 15 Common St: The annual concert by the Messiah Community Chorus performing selections from Handel’s Messiah. For details, see related post.
Thursday, December 11, 2025
Pop Up Art: Snowy House (5:00 – 6:30) @ Southborough Library: Ages 12 through adults can sign up for this free crafting program to create winter decor. (Registration is limited.) For details, see related post.
Saturday, December 13, 2025
New York City Bus Trip (6:00 am – about 11:00 pm) @ pickup & dropoff at Ashland Community Center: Book a deluxe motor coach trip for sightseeing during the holiday season through Southborough Rec. For details, click here.
Sunday, December 14, 2025
Interboro Community Band Winter Concert (2:00 pm) @ Westborough High School, 90 W Main St: A free symphonic concert for the public featuring “Seasonal Favorites & Other Music from the Symphonic Band Repertoire”. For details, see dedicated post.
AVM Messiah Sing (3:30 pm) @ Congregational Church of Westborough: Assabet Valley Mastersingers regional chorus will perform the Christmas portion of Handel’s oratorio and the “Hallelujah Chorus” with audience participation and organ accompaniment. For details, click here.
St. Mark’s School’s Lessons and Carols (5:00 – 6:30 pm) @ Belmont Chapel, St. Mark’s School: The public is invited to attend the annual Service of Nine Lessons and Carols for Christmas.
Tuesday, December 16, 2025
ARHS Holiday Concert (6:30/7:00 pm) @ Algonquin Regional High School Auditorium, 79 Bartlett St, Northborough: The school’s annual Christmas concert traditionally brings together both instrumental and vocal groups. Festivities begin in the rotunda at 6:30 pm. The main concert in the auditorium starts at 7:00 pm.
Wednesday, December 17, 2025
Blue Christmas Service (7:00 – 8:00 pm) @ St Mark’s Episcopal Church: This community wide service of prayers, readings and candles offers solace to those who need it during the holiday season. Open to all.
Saturday, December 20, 2025
St. Anne’s Christmas Pageant (6:00 pm) @ St. Anne’s Church, 20 Boston Rd: Children’s pageant, dinner, and basket raffle after the 5:00 pm mass.
Pilgrim’s Family Holiday Breakfast (8:15 – 9:30 am) @ Pilgrim Congregational Church’s Fellowship Hall, 15 Common St: Annual family event.
Tuesday, December 23, 2025
NSBORO Schools early dismissal for Holiday break: Public Schools of Southborough and Northborough start the winter break with an early dismissal. School doesn’t resume until January 5th.
Wednesday, December 24, 2025
Assabet Holiday break: Assabet Valley Regional Technical High School’s break starts this day. School doesn’t resume until January 5th.
Wednesday, December 24 & Thursday, December 25, 2025
Christmas Eve & Christmas Day religious services @ Southborough churches: Stay tuned for my annual dedicated post listing Christmas Masses, Candlelight Services, Carols, Pageants & Celebrations at the seven churches in town.
Wednesday, December 31, 2025
Welcome to 2025 Party (11:00 am – 12:00 pm) @ Woodward School: Registration is required for this special event by Southborough Recreation. The party for 0-12 yr olds (accompanied by adults) will include a DJ, snacks, games, and a photobooth. Formal wear is requested, not required. $10/child, max $25/ family. For details, click here.
Welcome to 2025 Party (2:00 – 3:00 pm) @ Southborough Library: Free children’s New Years party sponsored by the Friends of the Southborough Library. Children of all ages are invited to ring in 2026 a few hours early with crafts, activities, and snacks. No registration is required.