Halloween, a bunch of trucks and dog parades.
Halloween is a week from Saturday, so this is the warm-up weekend and it’s packed. I plan to try to take advantage of what is likely the last few weeks of beautiful New England fall before hibernation season. There is a ton of daytime family friendly Halloween things including Falloween at Drumlin Farm which looks awesome. Reminder to make sure you have your outfits ready so you don’t have a last minute scramble (no shade - that’s usually us).
This weekend was full of boogers in our house so we kept it low key. Hope to enjoy the beautiful sunshine incoming!
Picks of the Week
The Track at Suffolk Downs, East Boston · Saturday, October 24, 11:00 AM–2:00 PM · Free · Register ahead (suggested) · All ages
Its pretty much touch-a-truck meets Halloween. Fire trucks, construction equipment and emergency vehicles that littles can climb into, plus face painting, bubbles, music and trick-or-treat bags while they last. 11 to noon is the sensory-friendly hour: sirens, lights and horns turned way down. These events are sound and stimulation overload (lots of truck horns going wild) so I wouldn’t plan on staying more than an hour (for your sanity).
Dedham Square · Saturday, October 24, 2:00–5:00 PM (rain date Sunday) · Free · Drop-in · All ages
The whole square trick-or-treats: 30–40 shops hand out candy (look for the ghost in the window), then decorated cars at the Registry of Deeds lot from 3 on with a giant inflatable, games, face painting, crafts and touch-a-truck. Sensory-friendly half hour 2:30–3. Live music on the Town Green 4–6. Parking should be available in the square
Drumlin Farm, Lincoln · Saturday, October 24, 9:00 AM–5:00 PM · $12 kids / $15 adults (members $8 / $10) · All ages
Hayrides (until 3:45), the Creepy Critter Mansion with snakes and bugs, a hay play area to climb and jump in, face painting, stories with the Drumlin Witch, an owl, live music, and cider donuts. Come in costume and get a free farm prize.
☔️ Bad Weather Backups
New England Aquarium · Saturday–Sunday, October 24–25 · Aquarium tickets · All ages
Hunt for pumpkins hidden in the exhibits, do a fall animal scavenger hunt, and handle animal skulls and bones with the educators. Costumes welcome, but nothing inflatable, lit up or pointy as those scare the animals.
Peabody Museum, 11 Divinity Ave, Cambridge · Saturday, October 24, 12:00–4:00 PM · Museum admission; activities free · All ages
Decorate a skull mask, make paper marigolds and a flapping monarch butterfly, and join a bilingual butterfly story and parade at 12:30 and 3. Live music starting at 2.
Boston Children’s Museum · Saturday, October 24, 5:00–8:00 PM · Tickets required in advance · All ages
An after-hours costume night: trick-or-treat through the whole museum and play in the exhibits. Buy tickets ahead
☀️ Outside Adventures
Wright’s Pond, 140 Elm St, Medford · Saturday, October 24, 1:00–3:00 PM · Free · Registration appreciated · All ages
The library’s “haunted” dolls escaped into the woods and the kids have to find them along the trails. Wear hiking shoes. Everyone goes home with a free book.
deCordova Sculpture Park, Lincoln · Sunday, October 25, 10:00 AM–12:00 PM · $10 per person (members $5) · Tickets required · Toddlers & preschoolers
Little ones crawl through a giant rope spider web and hunt for spider sculptures with the educators. Costumes encouraged. A dog costume contest at 11.
Stone Zoo, Stoneham · Saturday, October 24, 10:00 AM–2:30 PM · Included with zoo admission · All ages
Snow leopard crafts for kids, a keeper talk at the Himalayan Highlands habitat, and facts about where they live in the wild.
📚 Library Picks
Putterham Library, Brookline · Monday, October 26, 7:00–8:00 PM · Free · All ages
Live owls up close, brought in by Mass Audubon. A great weeknight adventure if you’re kids stay up a little later than mine.
Cary Memorial Library, Lexington · Tuesday, October 27, 6:30–8:00 PM · Free · Drop-in · All ages
NAme says it all. some scary stories and some creepy crafts in the Library.
Winchester Public Library · Thursday, October 22, 4:30–5:30 PM · Free · Registration required · Grades K–3
The names this week are good. This one you make monsters out of pom poms.
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Fun for the whole family
Church Street YMCA, 276 Church St, Newton · Saturday, October 24, 2:00–4:00 PM · Free · Drop-in · All ages
A baby animal petting zoo, pumpkin decorating, music, games and giveaways. Costumes welcome.
Summer Street Plaza, Downtown Crossing · Saturday, October 24, 12:00–3:00 PM · Free · All ages
I mean - a parade of dogs dressed up in costumes? What more can you ask for? apparently face painting, a photo booth and free treats. There’s a “Best Dog and Child Duo” prize if your kid and dog want to match.
Commander’s Mansion, Watertown · Saturday, October 24, 4:00–7:00 PM · Free; haunted house $5 in advance ($10 at the door, under 3 free) · All ages
A trunk-or-treat with local businesses, kids’ games, ghost stories by flashlight, a costume contest and a dance party.
Assembly Row, Somerville · Sunday, October 25, 1:00–3:00 PM · Free · Drop-in · All ages
Trick-or-treat store to store around Assembly Row. Start on The Lawn for the map. If you can, bring warm socks, hats or travel-size toiletries for the Somerville Homeless Coalition.
Charles River Esplanade · Sunday, October 25, parade meets 9:45 AM · Free to watch or join ($15 suggested donation) · All ages
A new dog costume parade along the river, with costume awards at 10:30, during the Esplanade’s Fall Fest run and walk.
🎄 New guide: Christmas markets near Boston
I know, it’s not even Halloween. But Snowport opens November 6 and the good weekends fill up fast, so we put every market’s 2026 dates in one place: Christmas markets near Boston with kids.
And for the rest of October:
Halloween & pumpkin festivals near Boston — what’s still on the calendar through the 31st.
Pumpkin patches near Boston — several close after this weekend, so check before you drive.
Fall foliage hikes near Boston — ten walks with real color and short enough legs.
The Full Rundown
Thursday, October 22
Jack-O’-Lantern Nights (evenings Thu–Sun through Nov 1) — Stone Zoo, Stoneham · Tickets · All ages
Friday, October 23
Kids’ Crafts (4:00 PM) — Newton Free Library · Free · Ages 5+
Saturday, October 24
Gardening Workshop with Green City Growers (10:00 AM) — Central Library lawn, Somerville · Free · All ages
Sensory Storytime (2:00 PM) — Hunneman Hall, Brookline Village Library · Free · All ages
Sunday, October 25
SoWa Open Market (11:00 AM) — South End, Boston · Free · All ages
Monday, October 26
LEGO Lovers (3:00 PM) — Coolidge Corner Library, Brookline · Free · Ages 5–9
Tuesday, October 27
Baby Lapsit (9:30 AM) — Medford Public Library · Free · Drop-in · 0–24 months
Wednesday, October 28
My First Storytime (10:30 AM) — Newton Free Library · Free · 0–23 months
See all 326 events this week → the full calendar
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Have an awesome week. Dito signing off.
