BOO Bags, pumpkin festivals, costume concerts, and more spooky—and not-so-spooky—family fun!

Halloween night comes but once a year, but the fun lasts all month! Like ghosts in a graveyard, family-friendly Halloween happenings are popping up across Wellesley, Needham, Dedham, and nearby towns.

We stirred up a little Macaroni KID magic and—BOO!—gathered this list of spooky and not-so-spooky events for your family to enjoy. Grab your costumes, mark your calendars, and share with your fiendish friends. You won’t want to miss a thing!

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Please check with organizers before heading out, as schedules, availability, and registration requirements may change.

👻 Macaroni KID BOO Bags Are on Their Way!

For families who signed up for our 2026 BOO Bag program

Our Macaroni KID BOO Bags are starting to make their way to families in Wellesley, Needham, and Dedham! If you signed up, keep an eye on your email for selection updates and delivery or pickup instructions.

Receiving a bag? Enjoy your treats, then fill the extra bag and surprise another family to BOO-it-forward!

🎃 Wellesley Hills Church Pumpkin Patch

Through October 31 | Daily, 10 a.m.–6 p.m.
Location: Wellesley Hills Congregational Church, 207 Washington Street, Wellesley
Cost: Pumpkin prices vary

Choose a pumpkin for carving, decorating, or displaying at the Hills Church Pumpkin Patch. This annual fundraiser supports the church’s Youth Service Trip and the Wellesley Food Pantry—a festive way to support the community while picking out your perfect pumpkin!

🎶 Halloween Concert: Vanessa Trien and the Jumping Monkeys

Friday, October 23 | 6–7 p.m.
Location: The Green at Legacy Place, near J.Crew, Dedham
Cost: Free; tickets required for all attendees

Put on your costumes and get ready to dance! Boston’s beloved, Parents’ Choice Award-winning band Vanessa Trien and the Jumping Monkeys brings an interactive Halloween concert to Legacy Place.

Expect singing, dancing, jumping, spinning, imaginative play, and bubbles! The October 23 event is listed from 6–7 p.m.

Register: Download the Legacy Place Insider App to access free tickets for everyone attending. Visit the Legacy Place events page for more information.

🎤 Acatober at Wellesley High School

Friday, October 23, and Saturday, October 24 | 7–9:30 p.m.
Location: Katherine L. Babson, Jr. Auditorium, Wellesley High School, 50 Rice Street

Add music to your October plans with Acatober, featuring Wellesley High School’s choral and a cappella performers alongside guest groups.

The school’s official calendar lists performances from 7–9:30 p.m. both nights. Check ticket availability before attending.

🍂 Needham Fall Family Day

Saturday, October 24 | Activities from 9:30 a.m.–5 p.m.
Location: Needham Public Library, Greene’s Field, and downtown Needham
Cost: Most activities are free; Spooky Walk requires paid registration

Start with Slightly Spooky Story Time at the library, then head to Greene’s Field for afternoon fun!

Highlights include a petting zoo, Halloween storytelling, mini golf, inflatables, crafts, and a 3–5 p.m. concert by the Tear Downs.

The Spooky Walk offers organized trick-or-treating through downtown businesses. Registration is $12 in advance or $20 the same day.

Visit Needham’s Fall Family Day page for the full schedule and registration details.

👻 Halloween at Fay School

Saturday, October 24 | 10 a.m.–noon
Location: Fay School Quad, Southborough
Cost: Free

Designed for children ages 8 and under, this celebration with Fay School and the Southborough Library includes crafts, games, music, and costume fun.

• 10:15 a.m.: Storytime
• 10:45 a.m.: Children’s Costume Parade
• 11:15 a.m.: Halloween concert featuring Lindsay Munroe

Crafts and games take place throughout the event. Parents or guardians must accompany children, and supplies are limited.

Parking is available at Fay’s East Entrance, 23 Middle Road, with additional options listed on the event website.

🎃 Volante Farms’ PumpkinFest

Saturday, October 24 | 1–5 p.m. | Rain or shine
Location: Volante Farms, 292 Forest Street, Needham
Admission: $10; children under 2 are free

Carve a pumpkin for a good cause! Volante Farms’ 14th Annual PumpkinFest benefits Cradles to Crayons and brings families together for an afternoon of fall fun.

Enjoy unlimited pumpkin carving, face painting, a photo booth, balloon twisters, snacks and treats, and a lit pumpkin stroll.

Entertainment schedule:

• 1 p.m.: Magician Matt Roberts
• 2:30 p.m.: Big Joe the Storyteller
• 4 p.m.: Music by Backwards Hats

Visit Volante Farms for more information.

🧡 West Suburban YMCA Fall Festival

Saturday, October 24 | 2–4 p.m.
Location: 276 Church Street, Newton
Cost: Free and open to the public

Enjoy an afternoon of autumn activities at the West Suburban YMCA! Planned attractions include pumpkin decorating, a baby animal petting zoo, music, games, snacks, and giveaways. The YMCA’s event listing confirms the October 24 date and afternoon hours.

🕸️ Weston High School Haunted House

Saturday, October 24 | 6–8 p.m.
Location: Weston High School, 444 Wellesley Street, Weston
Admission: $15 per person or $45 per family

Looking for evening Halloween fun? Weston High School’s annual haunted house includes a children’s area for younger visitors, plus snacks and beverages for purchase.

Admission is payable at the door by cash or card, with proceeds supporting the sophomore class. Check with organizers about the scare level before bringing younger children.

💀 Halloween Skele-bration at Jammin With You

Two sessions: 3:45–4:45 p.m. or 5:15–6:30 p.m.
Cost: $25 for the first child; $20 for each additional child
Date and location: Check the registration page

Come in costume and get ready to JAM with Josh and friends! Jammin With You’s annual Halloween Skele-bration features musical fun and its signature campfire.

Organizers say this popular celebration sells out each year, so advance registration is encouraged.

Visit Jammin With You’s website to confirm the date and location and register.

🏠 Nominate a Spooktacular Wellesley House

Nomination deadline: October 28

Have a neighbor whose decorations deserve applause—or a friendly scream? Wellesley’s Howlin’ Haunted Halloween House Decorating Contest recognizes homes in two categories: Scariest and Judges’ Choice.

Email a photo and the home’s address to recreation@wellesleyma.gov. For displays with lights, include daytime and nighttime photos.

🍬 Wellesley Halloween Stroll

Saturday, October 31 | 11 a.m.–1 p.m.
Location: Start at Clock Tower Park, 291 Washington Street, Wellesley Hills
Cost: Free

Give those costumes a daytime outing! Families can trick-or-treat at participating Wellesley Hills businesses and enjoy games, music, and treats at the park.

The event is especially suited to children ages 0–8. Remember to bring your own trick-or-treat bag!

Visit Wellesley Recreation’s Halloween Stroll page for details.

🌙 Halloween Night: Saturday, October 31

Save room for neighborhood trick-or-treating! Coordinate with neighbors about timing, bring a flashlight or glow sticks, and watch for participating homes with their porch lights on.

Keep the family fun going! Visit the Macaroni KID calendar and subscribe to our free weekly newsletter for local events, seasonal guides, and community updates.