Above: A look at some of the events taking place in (or linked to) Southborough over the coming week. (images from flyers, promos, and contributed photos)
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, September 19, 2025
- NEF’s Applefest Gala – (7:30 pm – 11:00 pm) @ Juniper Hills Pavillion: Dress up for cocktails and dancing to live music sponsored by Education Foundation. (Northborough Education Foundation’s grants support Northborough’s public schools, including Algonquin Regional High School.) For details and tickets, click here.
- Live Music with JP White, DeRubeis & Caputo (8:00 pm) @ Owen O’Leary’s, 50 Turnpike Rd: Local musician JP White will perform new songs with Ryan Caputo, and Mario DeRubeis. For details, click here.
Saturday, September 20, 2025
- Northborough Applefest (9:00 am – 9:00 pm): Annual town festival with a slew of events with community ties through Algonquin and Boroughs youth groups/sports, capped off with fireworks. For details, see dedicated post.
- Pollination Potluck Picnic (11:00 am – 1:00 pm) @ Beals Preserve: Join the Bumble Bee Project at their picnic, hosted by Southborough’s Open Space Preservation Commission in collaboration with the Southborough Open Land Foundation. Reservations are required. For details, see dedicated post.
- Amanda Oakleaf Exhibit Closing Reception (11:00 am – 12:00 pm) @ Southborough Library: Reception for the artist displaying oil paintings at the library through September. For details, see related 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.
September 22, 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.
- 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.
Tuesday, September 23, 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.
- 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.)
- The Value of Validation (7:00 – 8:00 pm) @ Southborough Library: Registration is required for this session put on by Southborough Youth & Family Services as part of Suicide Prevention Awareness Month. Explore the power of validation in communication and how it can strengthen relationships and support mental health. 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, September 24, 2025
- 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.
- Nature Story Time (1:30 – 2:15 pm) @ Southborough Library, Children’s Room: This free program for 2-5 year olds requires pre-registration. The monthly story and craft series is put on by the Dept of Conservation & Recreation. This month’s focus is birds and bird songs. For details, see dedicated post.
- TLT: Pet Toys (4:30 – 5:30 pm) @ Southborough Library Main Floor: description. 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 toys for a local pet shelter, see dedicated post.
- 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, September 25, 2025
- Mah Jongg (10:00 am) @ Southborough Senior Center: The weekly program would love new players to join. Feel free to stop by to watch or talk to one of the players to see if you would be interested. For details, contact the Senior Center at 508-229-4453.
- Young Scientists STEM Beginnings (10:15 – 11:00 am) @ Southborough Library: This is a free series for children, ages 3-6 to learn STEM (Science, Technology, Engineering and Math) concepts through hands-on activities, story time and simple experiments. For details, see dedicated post.
- 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.
- ARHS College Fair (6:00 – 8:00 pm) @ ARHS gym: Algonquin will be hosting representatives of 100+ colleges and universities for their Post Secondary College Fair. All students and parents are welcome.
- Adult Game Night (6:30 – 8:30 pm) @ Southborough Library, main floor: Join fellow gamers to learn and play some new board games! Gamers are invited to try the library’s games or bring their own from home. For ages 18 and up.
- Karaoke (9:00 – 11:00 pm) @ Owen O’Leary’s, 50 Turnpike Rd: Weekly Karaoke night. For details, see related post.
Friday, September 26, 2025
- 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.
- Kids Jam (11:00 – 11:30 am) @ Southborough Library Children’s Room: Newborns through preschoolers are invited to dance and sing. No registration necessary. Sponsored by the Friends of the Southborough Library. For details, see related post.
- Canasta (11:15 am) @ Southborough Senior Center: A weekly card group playing “Hand & Foot”. For details, contact the Senior Center at 508-229-4453.
Saturday, September 27, 2025
- Yoga on the Trails (9:00 am) @ Sudbury Reservoir Trail: This free event for adults is put on by Southborough Trails Committee for National Parks & Recreation Month. Registration is required. For details, see related post.
Sunday, September 28, 2025
- Finn Fall Festival (12:00 – 3:00pm) @ Finn School: For families of Finn students, the festival features food trucks, games, music, crafts, raffles, and more. (Parents should be on the lookout for messages from the school with more details.)
- 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.
