Above: The Southborough Gardeners Plant Sale, arts & entertainment, Food Trucks, and preparing for Memorial Day weekend are just some of the many events taking place this weekend through next. (photos by Beth Melo and bottom right by Kim Tolander)
Here are highlights of what’s happening around (or related to) our town this weekend through the long Memorial Day weekend.
(The gray font below is for previously established long running events that take place weekly or bi-weekly.)
Friday evening, May 15, 2026
- ARHS Spring Improv Show (7:00 pm) @ Algonquin’s Black Box Theater: GonkStage’s annual improv and sketch comedy show. Tickets are available online only. For details, click here.
- Live Music with Acoustic Ménage (8:00 – 11:00 pm) @ Owen O’Leary’s, 50 Turnpike Rd: The band will entertain with acoustic favorites. For details, click here.
Saturday, May 16, 2026
- Southborough Gardeners Plant Sale (8:00 am – 12:00 pm) @ Community House lawn, 28 Main Street: The annual spring fundraiser in which Southborough Gardeners sell a variety of plants from members’ gardens including annuals, perennials, and hanging baskets. For details, see dedicated post.
- Spring Market (10:00 am – 3:00 pm) @ Apothecary Artists, 11 Main St: Join us for an indoor/outdoor market with spring shopping from local vendors and food trucks. For details, see dedicated post.
- TLT: Seed Pod Making (5:00 – 6:00 pm) @ Southborough Library Main Floor: Registration is required for this special program for 6th-8th grade volunteers. Participants will make pods of native seeds. For details, see see related post.
- Everyday Safety for Teen Girls (1:00 – 2:00pm) @ Southborough Library: Registration is required for this program for students ages 12+. Local teen volunteers will lead a relaxed session to help girls feel more confident navigating everyday situations. For details, click here.
- 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.
- Art Reception for Visions of Landscapes and Romanticism (6:00 – 8:00pm) @ Apothecary Artists, 11 Main St: Reception for the art exhibit by painter Gary Smith. For details, see dedicated post.
- Crossroads: A Night of Storytelling (7:00 pm) @ Southborough History & Arts Center, 42 Central St: The first Moth-style storytelling event in Southborough, featuring multiple StorySlam champs. Tickets are required. For details, see dedicated post.
Sunday, May 17, 2026
- Shir Joy Spring Concert (7:00 pm) @ Congregation B’nai Shalom, 117 East Main Street, Westborough: The regional Jewish community chorus concert is themed “Lights, Camera, Tradition!” For details, see dedicated post.
Monday, May 18, 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 the 2nd, 3rd & 4th Monday of each month.
- 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.
- ARHS Senior Scholastic Awards Night (6:30 – 8:30 pm) @ Algonquin Regional High School: Night to honor seniors receiving scholarships and scholastic awards. (Families should receive emails if there student is receiving an award.)
Tuesday, May 19, 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.
- Tri-M Coffeehouse (7:00 – 9:00 pm) @ Algonquin Regional High School, Cafeteria: ARHS’ musical honor society’s annual fundraising open mic night. Admission is free. Concessions will be for sale.
- Befriend Your Sleep (7:00 – 8:00 pm) @ zoom: Registration is required for this free interactive workshop to learn tools and strategies to help you sleep better. This is offered through a partnership between the Southborough Library and Jill Vroman Fitness & Wellness. For details, click here.
- Middle School Parent & Caregiver Focus Groups (7:00 – 7:45 pm) @ zoom: This is a focus group run by Encompass (the Northborough & Southborough community coalition focused on preventing and reducing substance misuse). For details, see dedicated 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, May 20, 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: New weekly time for people to play the game at the library. Drop ins are welcome, but groups of 4 are generally necessary to play. For details, click here.
- Food Truck Festival (3:30 – 7:00pm) @ St. Mark’s meadow (corner of Rte 85 and Rte 30): Part of the annual series organized by the Southborough Rotary Club featuring trucks selling dinner and ice cream. The event takes place on Wednesday evenings over four weeks. For details, see dedicated post.
- Meditations for the Nations (4:30 – 5:00 pm) @ St. Mark’s Church Parish Hall, 27 Main St: The church invites community members troubled by “division, unrest, and fear in our country” to share concerns with others and take part in guided and silent meditation. The bi-weekly program is open to all. For details, see dedicated post.
- ARHS Spring Art Show Reception (6:00 – 8:00pm) @ Algonquin Regional High School: Reception for the exhibit of student artwork. (The exhibit is also on display during school hours through May 18-29.)
- Virtual Author Talk (7:00 – 8:00 pm) @ online: Registration is required to take part in the free live talk with Q&A, “Dangerous Magic, Enchanting Romance, and Painting the Future with Elizabeth Lim”. 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.
- YA Watch Party for Elizabeth Lim Author Talk (7:00 – 8:00 pm) @ Southborough Library: Registration required. Readers in grades 6-12 are invited to watch the above-listed author talk live with fellow fans while enjoying snacks. For details, click here.
- Fay Memorial Park Community Engagement Meeting
(7:00 pm) @ zoom: Southborough Recreation is hosting this engagement event to help shape the future of the park and playground area on Central Street. For details, 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, May 21, 2026
- 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.
- 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.
- Blood Drive (12:00 – 6:30 pm) @ Southborough Library parking lot, 25 Main St: The Bloodmobile will be collecting blood. (If no spots are available to book, walk-ins are always welcome.) This month’s incentive for donors is a $15 gift card to Amazon. For details, see related post about past event.
- Middle School Parent & Caregiver Focus Groups (12:00 – 12:45 pm) @ zoom: This is a focus group run by Encompass (the Northborough & Southborough community coalition focused on preventing and reducing substance misuse). For details, see dedicated 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.
- NSPAC Go the Distance Awards (6:00 – 7:30pm) @ Algonquin Regional High School, 79 Bartlett St, Northborough: The Northborough/Southborough Special Education Parent Advisory Council’s 16th annual appreciation evening for community members who support students with special needs. For details, see dedicated post.
- Karaoke (9:00 – 11:00 pm) @ Owen O’Leary’s, 50 Turnpike Rd: Weekly Karaoke night. For details, see related post.
Friday, May 22, 2026
- 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.
- Canasta (11:15 am) @ Southborough Senior Center: A weekly card group playing “Hand & Foot”. For details, contact the Senior Center at 508-229-4453.
- ARHS Carnival (12:30 – 2:30 pm) @ Algonquin Regional High School: Algonquin’s annual festival for students run by student council with booths and activities organized by student groups.
- American Mah Jongg Meetup (1:00 – 3:30 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.
- Stand Up Now demonstration (3:00 – 4:00 pm) @ sidewalk corners of Rte 9, Central Street, and Oak Hill Road: The Southborough based pro-democracy group “Stand Up Now (SUN) has merged with “Indivisible Boros and Beyond”. Their formerly monthly “Stand Out” event is now being held weekly. The community is invited to join them holding up “pro-democracy” signs for passing commuters. For details, see related post/
- Mindful Art (4:00 – 5:30 pm) @ Southborough Senior Center, 9 Cordaville Rd: Registration is required for this free even for ages 5 through adults. (Kids under 16 yrs old must be accompanied by an adult.) Participants will take part in an art activity exploring personal roots. For details, see dedicated post.
- Flag placement for Memorial Day (6:00 – 7:00 pm) @ Rural Cemetery, Cordaville Road/Route 85: Community members are welcome to join veterans and volunteers placing/replacing fresh flags on veterans’ graves. To participate, meet them in front of the stone structure by the maintenance building at the rear of the cemetery.
Saturday, May 23, 2026
- Murph Challenge (8:00am – 12:00pm) @ ForceField Athletics, 94 Main St, Northborough: Algonquin’s student group Operation Enduring Freedom organizes local participation in the annual fundraiser for the LT. Michael P. Murphy Memorial Scholarship Foundation. For details, see last year’s post, and click here to register.
- ARHS Junior Prom (7:00 – 11:00 pm) @ Union Station: Algonquin’s prom night
Monday, May 25, 2026 – Memorial Day
- Schools and Public offices closed for the federal holiday.
- Memorial Day Parade & Observances (9:00 am): Each year, the VFW and American Legion invite the community to join them “as we remember those who have gone before us and especially those who gave the ultimate sacrifice.” A parade of veterans, scouts, and school bands convenes in Main St Bank parking lot, then proceeds down Main St, left onto Cordaville Road, and through the Town’s cemeteries, with ceremonies along the way to remember veterans laid to rest. The public is encouraged to follow along. Observances will end at the All Wars Memorial with the traditional speakers and ARHS singers.

