Things To Do around Westwood This Weekend and Beyond: Friday, October 16 - Thursday, October 23 (Updated)

Coming up this weekend and into next week:

• Fall sports are underway, with plenty of opportunities to view the Wolverines in home games at Westwood High School, during the weekend as well as weekdays. 

• The Pumpkins With A Purpose patch is open at First Parish, with 100% of net proceeds going to a charitable cause.

• Hale Education hosts its Great Pumpkin Smash, a friendly mountain biking competition through the reservation.

• Local quilters showcase over 100 creations at the Crosstown Quilters Guild Quilt Show. 

• Westwood Democrats welcomes new members as they hold elections and a general meeting.

Subscribe to Westwood Minute's newsletter to stay up to date on local events and things to do!

FIELD HOCKEY: Hopkinton v. Westwood- Fri Oct 17 4:00 pm

Westwood High School Multi-Purpose Field

Westwood' Varsity Girls Field Hockey (7-6-2) takes on Hopkinton (6-4-4) at home at Westwood High School. [more details]

FOOTBALL: Dedham v. Westwood- Fri Oct 17 7:00 pm

Westwood High School Flahive Field

The Wolverines take on the Marauders at home. Tickets are $7 for adults and $6 for students (plus a $1 fee per ticket), and are available here. [more details]

Crosstown Quilters Guild Quilt Show - Sat Oct 18 & Sun Oct 19 10:00 am

Cardinal Cushing Center

Local quilters from the south shore and surrounding towns will be among those represented in the upcoming Crosstown Quilters Guild Quilt Show “Wrapped in Comfort in the Garden” on Saturday from 10 AM to 4 PM and Sunday from 10 AM to 3 PM. This event will showcase over one hundred quilts made by Crosstown Quilt Guild members. 
[more details]

Pumpkins With A Purpose - Sat Oct 18 10:00 am & Sun Oct 19 11:30 am

First Parish of Westwood

On weekends in October, buy a pumpkin from the pumpkin patch where 100% of net proceeds support the church's outreach and service program. Past beneficiaries have included New Life Furniture Bank, Lifeworks, Rosie's Place, Pine Street Inn, Westwood Food Pantry and more. Saturday hours are 10 AM to 5 PM and Sunday hours are 11:30 AM to 5 PM.  [more details]

Great Pumpkin Smash MTB Road Race - Sun Oct 19 9:00 am

Hale Education

From 9 AM to 2 PM, join us for this 4-mile course on some of Hale's best trails. This event is designed as an XC Olympic (XCO) format race, and has opportunities for racers of all ages and abilities. Family members are welcome to attend as spectators and competitors. [more details]

Westwood Democrats Fall Meeting and Elections - Sun Oct 19 2:30 pm

Westwood Public Library

The Westwood Democratic Town Committee will host a general and elections will be held for Board Members: President/Chair, Vice-President, Secretary, Treasurer and Affirmative Action Officer (two-year terms). New members are welcomed and encouraged to attend.  [more details]

FIELD HOCKEY: Dedham vs. Westwood- Mon Oct 20 5:30 pm

Westwood High School Flahive Field

Westwood's Varsity Girls Field Hockey (7-6-2) takes on the Marauders (4-8-3) at home. [more details]

VOLLEYBALL: Hopkinton vs. Westwood- Mon Oct 20 6:00 pm

Westwood High School Gym

Westwood's Varsity Girls Volleyball (8-7) hosts Hopkinton (12-4) at home. [more details]

SOCCER: Hopkinton vs. Westwood- Tues Oct 21 6:00 pm

Westwood High School Flahive Field

Westwood's Varsity Girls Soccer (10-3-1) meets Hopkinton (9-1-1) on Westwood's Flahive Field. [more details]

VOLLEYBALL: Dedham vs. Westwood- Wed Oct 22 6:00 pm

Westwood High School Gym

Westwood's Varsity Girls Volleyball (8-7) plays Dedham (3-13) at home. [more details]

UNIFIED BASKETBALL: Westwood vs. Dedham - Thurs Oct 23 4:00 pm

Westwood High School Gym

Westwood's Coed Unified Basketball (1-1-1) takes on Dedham High School (1-2) in Westwood. [more details]

SOCCER: Dedham vs. Westwood- Thurs Oct 23 6:00 pm

Westwood High School Flahive Field

Westwood's Varsity Boys Soccer (7-3-4) meets Dedham (6-7-1) on Flahive Field. [more details]

---

You're in the loop! To add your event to our community calendar, just register for an account and post. It's free!

Updated 10/16/2025 at 10:09 p.m. Information for Pumpkins With a Purpose has been added.

You may also be interested in:

- Public Planetarium Program: Spooky Skies 4PM and 6PM (Calendar event)

- Not-So-Spooky Trunk or Treat (Calendar event)

- Interfaith Walk to End Hunger (Calendar event)

- Westwood Public Schools Holding Community Forums on Town's Facilities Study