Above: Fun events over the next week include three fundraisers (images of flyers)
Here are highlights of what’s happening around (or related to) our town this weekend through next weekend.
(The gray font below is for previously established long running events that take place weekly or bi-weekly.)
Friday evening, November 21, 2025:
- Once Upon A Mattress (7:00 – 9:30 pm) @ Algonquin Regional High School, 79 Bartlett Street, Northborough: The 2025 ARHS Fall Musical is a comedic retelling of The Princess and the Pea. For details, see dedicated post.
- Live Music with Dave Parker (8:00 pm) @ Owen O’Leary’s, 50 Turnpike Rd: The singer/musician will entertain with a mix of classic hits and crowd favorites.. For details, click here.
Saturday, November 22, 2025
- First Community Church’s Pie Sale (8:00 – 11:00 am, or sooner if they sell out!) @ outside Mauro’s Village Cafe, 2 Main Street: Church volunteers are holding their 35th annual Pie Sale. For details, see dedicated post.
- ARHS Dodgeball Tournament (9:00 am – 5:00 pm) @ Algonquin Regional High School, 79 Bartlett Street, Northborough: Co-Ed Dodgeball competition for 1st-8th graders. Team registration is due by Friday, November 14th, but anyone can attend to cheer players on. For details, see dedicated post.
- Safer Spaces Project – Youth Meeting (7:00 – 9:00 pm): Event for grades 6-12 hosted by Safer Spaces for LBGTQ+ youth of all faiths and their allies. Tonight, they’ll enjoy music and musical trivia. For details, see their Facebook post.
- Painting With Julie (11:00 am – 12:00 pm) @ Southborough Library: Registration is required for this free program for kids ages 8-12 to paint “A Bear in Winter”. For details, see related post.
- Photos with Santa to benefit local organizations (2:00 – 4:00pm) @ Aurora Aesthetics and Wellness Center, 54 Central St: The event is free, but community members are encouraged to make a donation to Southboro Free Fridge & Project Just Because. For details, see dedicated post.
- Once Upon A Mattress (7:00 – 9:30 pm) @ Algonquin Regional High School, 79 Bartlett Street, Northborough: The 2025 ARHS Fall Musical is a comedic retelling of The Princess and the Pea. For details, see dedicated post.
Sunday, November 23, 2025
- Winter Market (10:00 am – 3:00 pm) @ where: Shop locally this holiday season at Southborough’s annual sale featuring local artisans and vendors. Find handmade items for everyone on your shopping list or book a holiday photoshoot. For details, see dedicated post.
- Heritage Chorale Concert (4:00 pm) @ St. Mark’s School, Putnam Family Arts Center: The fall concert will feature Mozart’s Requiem. For details, see dedicated post.
- St. Mark’s Messy Church (4:00 – 6:00 pm) @ St Mark’s Episcopal Church Parish Hall, 27 Main St: A worship experience for busy families of younger kids. Includes a Bible story theme with activities, crafts, and a shared meal. For details, see related post.
Monday, November 24, 2025
- Walking Group for Seniors (8:30 am) @ Trottier Middle School’s outdoor track: Free weekly walking group organized by the Southborough Senior Center. Walkers generally go for an hour, but continue for as long as you wish. The location is a loop, so feel free to join late.
- Preschool Story Time (10:30 – 11:15 am) @ Southborough Library Children’s Room: Ages 2-5 are invited for stories and a craft based on a weekly theme. No registration required. For details, see related post.
- Rummikub (11:00 am) @ Southborough Senior Center: A new game group for seniors, meeting twice monthly. For details, contact the Senior Center at 508-229-4453.
- Knitting Club & Quilting Club (1:00 pm) @ Southborough Senior Center: Weekly opportunity for senior crafters to work on their projects in a social setting, including knitting, sewing, cross stitching, needle point. For details, see related post.
- Reading Buddies (3:30 – 4:30 pm) @ Southborough Library: Registration is required for this program (weekly Oct 20th through Dec 15th) that pairs readers in training (ages 5+) with teen reading buddy volunteers. For details, see dedicated post.
- DIY Thanksgiving Centerpiece Workshop (6:30 pm) @ Gulbankian Florist, 40 Mt Vickery Rd: There is a registration fee and attendance is limited. For details, see related post.
Tuesday, November 25, 2025
- Preschool Story Time (10:30 – 11:15 am) @ Southborough Library Children’s Room: Ages 2-5 are invited for stories and a craft based on a weekly theme. No registration required. For details, see related post.
- Bridge (12:00 pm) @ Southborough Senior Center: A weekly card group, welcoming new participants. For details, contact the Senior Center at 508-229-4453.
- Comics Club (4:30 – 5:30 pm) @ Southborough Library: Registration is required for this free program for Children age 7 and older (with their siblings or adults). Discus comics and do some drawing with graphic novelist and comics instructor Jonathan Todd. For details, see related post.
- DIY Oranges & Lemons Workshop (6:30 pm) @ Gulbankian Florist, 40 Mt Vickery Rd: There is a registration fee and attendance is limited. For details, see related post.
- Poetry Workshop (6:30 – 8:30 pm) @ Southborough Library, main level: Bring in five copies of original poetry to share. The group will provide supportive feedback. If you don’t have a poem, come anyway and share your insights. (Meets twice monthly.)
- Shelf Help Discussion Group (7:00 – 8:00 pm) @ Southborough Library: A community book discussion group run by SYFS with the Southborough Library. This month’s focus is a novel exploring “themes of gratitude, kindness, and human connection”. Members should have pre-registered to participate (but pre-reading isn’t required). For details, see related post.
- Geeks Who Drink Trivia Night (8:00 – 10:00 pm) @ Owen O’Leary’s, 50 Turnpike Rd: Weekly Trivia game night with prizes. For details, see dedicated post.
Wednesday, November 26, 2025
- AVRTHS No School: Assabet students start their Thanksgiving break, through the weekend, with a full day off.
- Walking Group for Seniors (8:30 am) @ Southborough cemetery, 11 Cordaville Road: Free weekly walking group organized by the Southborough Senior Center. Walkers generally go for an hour, but continue for as long as you wish. The location is a loop, so feel free to join late.
- Early Dismissals for NSBORO Students: NSBORO schools start their Thanksgiving breaks (through the weekend) after a half day. (Dismissal times by schools are ARHS at 11:06 am, Trottier at 10:50 am, Neary at 11:50 am, Woodward at 12:05 pm, and Finn K-1 at 12:20 pm and Pre-K at 11:00 am.)
- TLT Kindness Rocks (12:00 – 1:00 pm) @ Southborough Library Main Floor: description. The library holds a monthly Teen Library Team volunteer program for ages 10-18 to make projects to help the community or good causes. This month volunteers will paint rocks with caring messages, see related post.
- Early Gobble Wobble Pre-Reg Check In (12:00 – 5:00) @ Trottier Middle School, 49 Parkerville Road: Register for the Thanksgiving Day Race. Or if you already did that online, pick up your bib and shirt. For details, see dedicated post.
- Live Music with Brennan Burns (8:00 – 11:00 pm) @ Owen O’Leary’s, 50 Turnpike Rd: For Thanksgiving Eve, the pub is bringing in Nashville singer-songwriter Brennan Burns, performing guitar driven, folksy/country-rock. For details, click here.
Thanksgiving — Thursday, November 27, 2025
- Town Holiday Break: Town offices and facilities, and the schools are all closed for the federal holiday.
- Gobble Wobble (7:30 check in & 8:30 am race) @ Trottier Middle School, 49 Parkerville Road: 19th Annual 5K race and 2 Mile Walk, raising funds for Friends of Southborough Recreation. For details, see dedicated post.
- ARHS Thanksgiving Day Football (10:00 am) @ Westborough High, 90 W. Main Street: Buy tickets online for the annual Turkey Day rivalry game. For details, see related post.
Friday, November 28, 2025
- Town Holiday Break: Town offices and facilities, and the schools are all closed for a Thanksgiving break.
- Black Friday: I encourage residents to consider Southborough businesses when you think about your holiday shopping. Click here for my Shop Local directory.
- SFA Christmas Tree Sales begin (1:00 – 8:00 pm) @ 32 Cordaville Road: The first day of the annual Christmas Tree Sale by Southborough Firefighters. The sale will continue daily (with differing hours) until they sell out. For details, see last year’s post and stay tuned for this year’s.
- 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.
Saturday, November 29, 2025
- Town Holiday Hours: The Transfer Station reopens for regular hours. The Library remains closed through the weekend.
- Small Business Saturday: I encourage the community to make a special effort to support at least one Southborough small businesses on this special shopping day, but also throughout the holidays. Click here for my Shop Local directory..
Sunday, November 30, 2025
- DIY Christmas Wreath Workshop (1:00 pm) @ Gulbankian Florist, 40 Mt Vickery Rd: There is a registration fee and attendance is limited. For details, see related post.
