Events this week

Above: Here’s a taste of some of the happenings on tap in Southborough tonight through next Sunday. (images cropped from flyers and contributed by Rotary)

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 16, 2026

• 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 “Intro to Programming + Problem Solving”. 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.

Monday, October 19, 2026

• Walking Group for Seniors (8:30 am) @ Trottier Middle School’s outdoor track: 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.
• 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.
• Rummikub (11:00 am) @ Southborough Senior Center: Drop-in to the game group for seniors, meeting certain Mondays of each month. For details, see the Senior Center newsletter here.
• 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.

Tuesday, October 20, 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.
• Spicy Ladies Club (11:00 am) @ Southborough Senior Center: A monthly social group for seniors. New members are welcome to drop-in. 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.
• 4th & 5th Grade Book Club (4:00 – 5:00 pm) @ Southborough Library, Eaton Room: Monthly Book Club with discussion and activities. Registration is required. For details, see related post.
• Fall Puzzle Race (6:00 – 8:30 pm) @ Southborough Library: Registration is required (and limited) for this competition teams of puzzlers ages 7+ racing to complete a 500 piece puzzle. For details, click here.
• ARHS Fall Chorus Concert (7:00 – 9:00 pm) @ Algonquin Regional High School: Performances by Algonquin’s Concert Choir, Camerata Singers, and Chamber Choir. For details, click here.
• 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 21, 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.
• 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.
• Crafternoon (4:30 – 5:30 pm) @ Southborough Library, main floor: Pre-registration is required for this free program for ages 8–12 years old. This session, make Pumpkin Witches For details, see related post.
• Mandala Mini Pumpkins (6:00 – 7:00 pm) @ Southborough Library, main floor: Craft workshop for adults and teens ages 12+. Registration is required. For details, see dedicated post.
• Southborough Rotary Club (7:00 – 8:00 pm) @ Southborough Library, main floor: Regular meeting of the Rotary Club of Southborough. New and prospective members are always welcome. (Held on the 1st & 3rd Wednesdays of the month.)
• 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 22, 2026

• Mah Jongg (10:00 am) @ Southborough Senior Center: A weekly group, welcoming new participants. For details, 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.
• 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 White Pumpkin and Succulents Centerpiece. For details, click here.
• YA Virtual Author Talk (7:00 – 8:00 pm) @ online: Registration is required to take part in the free live talk with Q&A with a Young Adult Author, “Ghosts, Grief, and Growing Up: YA Storytelling with Cherie Dimaline”. This is part of the Southborough Library’s virtual series featuring bestselling, award-winning, and highly acclaimed authors from around the world. For details, see related post.
• Karaoke (9:00 – 11:00 pm) @ Owen O’Leary’s, 50 Turnpike Rd: Weekly Karaoke night. For details, see related post.

Friday, October 23, 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.
• 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.
• Canasta (10:00 am) @ Southborough Senior Center: A weekly card group playing “Hand & Foot”. For details, contact the Senior Center at 508-229-4453.
• 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.
• 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 AK Cody (8:00 – 11:00 pm) @ Owen O’Leary’s, 50 Turnpike Rd: The Nashville Award-Winning Recording Artist will perform his original music and popular country covers. For details, click here.

Saturday, date, 2026

• Library Halloween Party at Fay (10:00 am – 12:00 pm) @ Fay School Primary School: Fay School is again hosting the Southborough Library’s annual Halloween party for kids. Includes a story time, costume parade, and concert. No registration required. For details, see dedicated post.
• CrossFit SOBO Open House (11:00 am – 3:00 pm) @ CrossFit SOBO 12 Southville Road: The gym’s Grand Re-Opening under the new business name. The public is invited in to enjoy food, music, entertainment, demonstrations, special offers and some giveaways. For more details, read dedicated post:
• Trunk or Treat (3:00 – 6:00 pm) @ Woodward School parking lot and the Public Safety Building: The annual parade and costume party at the fire station, combined with the Town’s trick or treating event (at parked car “trunks”). For details, see dedicated post.
• Live Music (6:30 – 10:00 pm) @ Lalo’s Mexican Kitchen & Bar, 154 Turnpike Rd: The restaurant is promoting live music in honor of Hispanic Heritage Month. 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 Movie Night PJ Party. 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 25, 2026

• 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.