Above: The big highlight of the week is this long weekend’s traditional festivities including the Pumpkin Stroll and Heritage Day. (photos by Beth Melo and from Facebook)
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, October 9, 2026
- Live Music with Ravenna (6:30 – 10:00 pm) @ Lalo’s Mexican Kitchen & Bar, 154 Turnpike Rd: The Brazilian singer will perform live.. For details, click here.
- 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 a Music Night. For details, click here.
- Live Music with Nikki Sinn (8:00 – 11:00 pm) @ Owen O’Leary’s, 50 Turnpike Rd: The musician will perform classic acoustic.. For details, click here.
Saturday, October 10, 2026
- Golf Fore ALS @ Southborough Golf Club: All long weekend, $10 from each player’s greens fees will go to ALS research and care. For details, see dedicated post.
- Assabet’s Trunk or Treat (3:00 – 6:00pm) @ Assabet Valley Regional Vocational Technical High School: Assabet is holding its 3rd annual Trunk or Treat festivities way ahead of Halloween. The event is a fundraiser and collection for a local food pantry. For details, click here.
- Live Music with Sebas (6:30 – 10:00 pm) @ Lalo’s Mexican Kitchen & Bar, 154 Turnpike Rd: The singer will perform live. For details, click here.
Sunday, October 12, 2025
- Golf Fore ALS @ Southborough Golf Club: All long weekend, $10 from each player’s greens fees will go to ALS research and care. For details, see dedicated post.
- Pumpkin drop-off (4:00 – 6:00 pm) @ Common Street: Drop-off your carved or decorated contributions to the Pumpkin Stroll display on the stone wall around the Old Burial Grounds.
- Pumpkin Stroll (6:00 – 8:00 pm) @ line up begins in front of 25 Main Street: The community is invited to view the big display of jack-o-lanterns. Sponsored by Southborough Rotary, which will be offering free refreshments and giveaways, while collecting donations for the Food Pantry (See the pantry’s latest needs list). For details, see dedicated post.
Heritage Day, Monday, October 13, 2025
- State holiday (for Columbus Day / Indigenous People’s Day): No public school. Town offices, Senior Center, and Library are closed.
- Golf Fore ALS @ Southborough Golf Club: All long weekend, $10 from each player’s greens fees will go to ALS research and care. For details, see dedicated post.
- Heritage Day (9:45 am – 2:00 pm) on the St. Mark’s field (at the intersection of routes 30 & 85) and nearby locations: The the annual town celebration of our community. While it honors the town’s history, it is rooted in the present, bringing together different segments of the community. For details, see dedicated thread.
- Town Parade (9:45 am): The Town’s biggest annual community parade departs from St. Anne’s Church on Boston Road, proceeds down Main Street, ending at Marlborough Road and St. Mark’s Street. For details, see dedicated post.
- KofC Soccer Challenge (10:00 am – 1:00 pm) @ St. Mark’s field (at the intersection of routes 30 & 85): Soccer penalty shot competition for ages 6-16. For details, see dedicated post.
- Heritage Day (10:00 am – 2:00 pm) on the St. Mark’s field (at the intersection of routes 30 & 85): Booths with exhibiting community groups, non-profits, and local vendors. For details, see dedicated post.
- Friends of Southborough Library Book & Bake Sale (10:00 am – 3:00 pm) @ Southborough Library parking lot: One free book per child. Selling used books, and more. There will also be a Bake Sale table. For details, see dedicated post.
- Fire Station Open House (11:00 am – 2:00 pm) @ Public Safety Building: The Southborough Fire Dept will open its garage bay to offer tours, live demos, and more. For details, see dedicated post.
Tuesday, October 13, 2026
- 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 (and sometimes a couple of songs). 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.
- 2nd & 3rd Grade Book Club (4:30 – 5:00 pm) @ Southborough Library, Eaton Room: Monthly Book Club with discussion and activities. Registration is required. For details, see related post.
- TLT (5:00 – 6:00 pm) @ Southborough Library Main Floor: The library holds a monthly Teen Library Team volunteer program for ages 10-18 to make projects for others in need. This month volunteers will make pet toys for a local shelter. 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.)
- 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, October 14, 2026
- Walking Group for Seniors (8:30 am) @ Southborough cemetery, 11 Cordaville Road: Free weekly walking group organized by the Southborough Senior Center. (Dependent on weather conditions.) 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.
- Elder Law Advice (10:00 – 10:45 am) @ phone or zoom: Southborough seniors can sign up for a free 15 minute session of individualized legal advice from an Elder Law attorney. For details, see related post.
- American Mah Jongg Meetup (1:00 – 4:00 pm) @ Southborough Library, Main Floor Stacks: Weekly opportunity to play. Drop ins are welcome, but groups of 4 are generally necessary. For details, click here.
- Intro to Wildlife Tracking for kids (4:30 – 5:30 pm) @ Southborough Library, main floor: Pre-registration is required for this free program for ages 5+. Hands on Nature will teach about tracks and other wildlife signs. For details, see dedicated post.
- DIY Gulbankian Workshop (6:30 pm) @ Gulbankian Florist, 40 Mt Vickery Rd: There is a registration fee and attendance is limited. This session is to make a Succulent Gourd Trio. For details, click here.
- Live Blues Jam n’ Open Mic (8:00 – 11:00 pm) @ Owen O’Leary’s, 50 Turnpike Rd: Come play or sing with the house band and fellow musical talent, or just enjoy the show. For details, see related post.
Thursday, October 15, 2026
- Mah Jongg (10:00 am) @ Southborough Senior Center: For details on the playing group, contact the Senior Center at 508-229-4453.
- Baby/Toddler Storytime (11:00 – 11:30 am) @ Southborough Library Children’s Room: A weekly program for ages 0-2 years with their parents/caregivers. Each session will include puppets and music. No registration required. For details, see related post.
- Genealogy Club (2:30 – 4:00 pm) @ Southborough Senior Center: The Club welcomes drop-ins to its monthly meeting by those interested in learning more about their own family history and genealogy. For details, see related post.
- Watershed Forests: Name that Tree (4:30 – 5:30 pm) @ Southborough Library: Registration is required for this free program run by DCR for ages 6–10 years old. In this event, kids will learn about local trees. For details, see related post.
- Sip & Paint Night (6:00 – 8:00 pm) @ Lalo’s Mexican Kitchen & Bar, 154 Turnpike Rd: The restaurant is promoting the program with two fall themed painting projects to choose from. For details, click here.
- Sachem Haunted Coffee House (7:00 – 10:00 pm) @ where: The seasonal “coffeehouse” features a variety of acts by Algonquin students to raise funds for the school’s literary and art magazine. Tickets are $10 to be purchased in advance here. For more details, click here.
- Karaoke (9:00 – 11:00 pm) @ Owen O’Leary’s, 50 Turnpike Rd: Weekly Karaoke night. For details, see related post.
Friday, October 16, 2026
- Wizards (9:00 am) @ Southborough Senior Center: The spinoff to the Dull Men’s Club meets immediately prior to discuss subjects relating to science and technology. New members are always welcome to drop in. For details, see related post.
- Dull Men’s Club (10:00 am) @ Southborough Senior Center: Casual social club for senior men. New members are always welcome to drop in. For details, see dedicated post.
- Canasta (10:00 am) @ Southborough Senior Center: A weekly card group playing “Hand & Foot”. For details, contact the Senior Center at 508-229-4453.
- Rhyme Time (11:00 – 11:30 am) @ Southborough Library Children’s Room: Weekly drop-in program for babies and toddlers (and parents/caregivers). Join Ms. Jenny for rhymes, songs, and more fun. For details, see related post.
- American Mah Jongg Meetup (1:00 – 4:00 pm) @ Southborough Library, Main Floor Stacks: Biweekly opportunity. Drop ins are welcome, but groups of 4 are generally necessary to play. For details, see related post.
- ARHS Homecoming Tailgate (5:00 pm until halftime) @ Algonquin Regional High School GonkPlex (in front of stadium): Starting before the 6:00 pm ARHS Homecoming Football game against Grafton, Boosters for ARHS Soccer are putting on a fundraising tailgate BBQ (accepting cash and Venmo). For details, click here.
- Live Music with Ravenna (6:30 – 10:00 pm) @ Lalo’s Mexican Kitchen & Bar, 154 Turnpike Rd: The Brazilian singer will perform live.. For details, click here.
- Live Music with Candy Criminals (8:00 – 11:00 pm) @ Owen O’Leary’s, 50 Turnpike Rd: The high-energy rock outfit, will perform with their “gritty riffs, raw vocals, and infectious charisma!” For details, click here.
Saturday, October 17, 2026
- Yoga on the Trails (9:00 – 10:00am) @ field off Parkerville Rd: The Southborough Trails Committee is sponsoring a series of free monthly outdoor yoga sessions (for adults only) with Emma Bartolini. Registration is required. For details, see dedicated post.
- Special Town Meeting (10:00 am) @ Trottier Middle School auditorium: All registered Southborough voters are encouraged to attend to act as the legislature by voting on decisions about spending, borrowing, and/or Town bylaws. For details, see dedicated post.
- Flake it to you Bake it! (12:00 pm) @ Southborough Senior Center: Intergenerational event featuring hot apple cider, making muffins or decorating sugar cookies. For details, contact the Senior Center at 508-229-4453.
- Intro to Robotics & Engineering (2:00 – 3:00 pm) @ Southborough Library, Eaton Room: Registration is required for this free hands-on lessons for grades 4-7. It’s part of a bi-weekly series on specific robotics & engineering topics. This session’s theme is “theme”. For details, see dedicated post.
- Sit & Knit (2:00 – 4:00 pm) @ Southborough Library: Semi-monthly program for ages 18+ to drop in and work on your latest knitting or crochet projects while you enjoy the company of fellow yarn crafters in a relaxed social setting. All levels are welcome but no formal instruction will be given.
- ARHS Homecoming Dance (6:00 – 9:00 pm) @ Algonquin Regional High School, large gym: Semi-formal Dance (themed “Under the Stars”. For details, click here.
Sunday, October 18, 2026
- Rotary Oktoberfest (1:00 – 5:00pm) @ Southborough Gazebo, 19 Main Street: 2nd annual fun-filled afternoon of German-inspired cheer, delicious eats, and community spirit, all while helping a vital local cause. Entertainment includes live music and the Patriots game on the big screen. For details, see dedicated post.
- DIY Gulbankian Workshop (2:00 pm) @ Gulbankian Florist, 40 Mt Vickery Rd: There is a registration fee and attendance is limited. This session is to make a Spooky Haunted Tree. For details, click here.
