Little Monsters, Big Weekend: 10 Kid-Friendly Things to Do in Connecticut
By The Krypt
October 16–18, 2026 | By The Krypt
Halloween memories can start with a pumpkin, a costume and a little curiosity. For families planning this weekend in Connecticut, The Krypt has plenty of ways to enjoy the season together—from a pumpkin-picking trolley ride to illuminated dinosaurs and an afternoon of trick-or-treating.
We checked Krypt Events and Krypt Maps to put together these ten outings for Friday, October 16, through Sunday, October 18. Nine have dated weekend events; one is a year-round bookshop stop with hours to confirm before visiting. Every pick is marked Kid Friendly on The Krypt, with the individual listing providing the details.
1. FOLLOW THE LIGHTS AT PUMPKIN PASSAGE — MONTVILLE
Dinosaurs and Halloween make a pretty irresistible combination. Pumpkin Passage at The Dinosaur Place brings together illuminated dinosaurs, pumpkins, entertainment, inflatables and marshmallow roasting for a family evening out.
For this weekend, the Friday and Saturday sessions run October 16–17, 5–9 p.m., with final admission at 8 p.m. The separately listed Sunday session runs October 18, 5–8 p.m. Tickets are listed at $28.62–$30.74; check availability for your chosen date.
Where: 1650 Hartford–New London Turnpike, Montville.
Friday and Saturday details on The Krypt:
https://thekrypt.app/events/pumpkin-passage
Sunday details:
https://thekrypt.app/events/pumpkin-passage-sunday-nights-montville-ct
2. RIDE THE PUMPKIN PATCH TROLLEY — EAST HAVEN
Turn pumpkin picking into a small adventure aboard the Shore Line Trolley Museum’s Pumpkin Patch Trolley. This daytime family outing pairs a trolley ride with a chance to pick a pumpkin.
The Krypt lists Saturday and Sunday, October 17–18, 10:30 a.m.–5 p.m., with the last trolley at 4 p.m. Choose your date through the listing’s ticket link for admission prices and availability.
Where: 17 River Street, East Haven.
Plan your trolley outing on The Krypt:
https://thekrypt.app/events/pumpkin-patch-trolley
3. SPEND A DAYTIME HALLOWEEN AT BERRY SCARY ACRES — TORRINGTON
At Ruwet Farm, Berry Scary Acres offers a corn maze, games and a haunted house that the operator describes as kid friendly. It is a daytime option for families who want a little Halloween atmosphere alongside farm activities.
The event is listed for October 16, 17 and 18, 10 a.m.–5 p.m. General admission is $7 per person, with children under 3 free. Some special activities cost extra. Parents can decide whether the haunted-house portion suits their child’s comfort level.
Where: 236 East Pearl Road, Torrington.
Explore Berry Scary Acres on The Krypt:
https://thekrypt.app/events/berry-scary-acres
4. DRESS UP FOR ALL HALLOWS AT THE CONNECTICUT RENAISSANCE FAIRE — LEBANON
Give those costumes an early outing at the Faire’s All Hallows weekend. The daytime program combines Halloween theming with shows, artisan shopping and food—a chance to make a longer family day of the season.
The Krypt lists October 17–18, 10:30 a.m.–6 p.m., with admission listed at $10–$18. This recommendation covers the daytime Faire; Halloween Knights is a separate evening program on Saturday.
Where: Lebanon Fairgrounds, 122 Mack Road, Lebanon.
See All Hallows weekend on The Krypt:
https://thekrypt.app/events/all-hallows-at-the-connecticut-renaissance-faire
5. HIT THE CANDY TRAIL AT DISCOVERY MUSEUM — BRIDGEPORT
Trick or Treat Fest packs crafts, characters, performances, a candy trail, games, music and food into a family Halloween day. It is a good pick when you want several activities in one stop.
The event takes place Saturday, October 17, 10 a.m.–2 p.m. Tickets are listed at $10.
Where: Discovery Museum, 4450 Park Avenue, Bridgeport.
Find Trick or Treat Fest on The Krypt:
https://thekrypt.app/events/trick-or-treat-fest-at-discovery-museum
6. DECORATE A PUMPKIN AT WILTON’S PUMPKIN FEST — WILTON
Pumpkin decorating, a scavenger hunt, lawn games, cider and donuts give Pumpkin Fest at the Wilton Historical Society a classic fall feel. Open-hearth cooking and blacksmithing add something for curious kids to watch and discover.
This all-ages event runs Saturday, October 17, 1–3 p.m. Admission is listed at $5; members are free.
Where: 224 Danbury Road, Wilton.
See Pumpkin Fest on The Krypt:
https://thekrypt.app/events/pumpkin-fest-2026
7. TAKE A FAMILY HAYRIDE AT CASTLE HILL FARM — NEWTOWN
For a daytime farm outing, Castle Hill Farm’s fall hayrides offer an approximately 20-minute ride with a stop to feed cattle. It is an easy seasonal choice for families who would rather enjoy the farm than a nighttime scare attraction.
This weekend’s dates are October 17–18, during listed farm hours of 10 a.m.–5 p.m. The hayride is listed at $7. Operation is weather permitting, so confirm before heading over.
Where: 1 Sugar Lane, Newtown.
Check Castle Hill Farm’s weekend hayrides on The Krypt:
https://thekrypt.app/events/castle-hill-farm-remaining-fall-hayride-weekends-newtown
8. BRING A TREAT BAG TO THE CONNECTICUT SCIENCE CENTER — HARTFORD
The Connecticut Science Center’s Spooktacular adds building-wide trick-or-treating, crafts, a photo booth and seasonal giveaways to a family museum visit. Costumes are encouraged, and the listing recommends bringing a trick-or-treat bag.
The Halloween activities run Sunday, October 18, 10:30 a.m.–2:30 p.m. They are included with general admission; museum admission is still required.
Where: 250 Columbus Boulevard, Hartford.
Plan a Spooktacular visit on The Krypt:
https://thekrypt.app/events/spooktacular-at-the-connecticut-science-center
9. ENJOY A FREE TRUNK-OR-TREAT IN WATERFORD
Waterford’s Wicked Wonderland Trunk-or-Treat brings costumes, music, contests, inflatables and food vendors to the high school’s circular parking lot. Bring a candy bag and let the kids enjoy an early round of Halloween treats.
The free public session is Sunday, October 18, 2–4 p.m. A separate neurodivergent-friendly session runs 1–1:30 p.m. Children under 12 must remain with an adult. Food purchases are separate from free event admission.
Where: Waterford High School, 20 Rope Ferry Road, Waterford.
Find Waterford’s Wicked Wonderland on The Krypt:
https://thekrypt.app/events/waterford-s-wicked-wonderland-trunk-or-treat
10. BROWSE ALICE’S HAUNTED LITTLE BOOKSHOP — MYSTIC
For a flexible stop between scheduled activities, visit Alice’s Haunted Little Bookshop, a Victorian-themed specialty bookstore filled with dark, mysterious and unusual books, curios and themed decor.
The Krypt lists it as a year-round, public, kid-friendly place. Parents can help younger readers choose books that suit them while enjoying the setting together. Current hours are not listed, so confirm opening times before making it part of your weekend.
Where: 27 Coogan Boulevard, #26B, Mystic.
Discover Alice’s Haunted Little Bookshop on The Krypt:
https://thekrypt.app/places/alice-s-haunted-little-bookshop-mystic
MAKE THE WEEKEND YOUR OWN
Pick the outing that fits your family’s pace: a daytime trolley ride, a short pumpkin festival, a free community celebration or an evening beneath glowing dinosaurs. You do not have to fit all ten into one weekend to give your little monsters a memorable October.
Explore Krypt Events for dated plans and Krypt Maps for places to build an outing around. Check the individual listing and its booking link before leaving for ticket availability, weather changes and current hours.
https://thekrypt.app/events
https://thekrypt.app/map
Article information comes exclusively from The Krypt’s public event and place listings, checked October 16, 2026. Dates and times are local to Connecticut. Prices are those listed when checked and may change.
PHOTO CREDIT
Shore Line Trolley Museum, home of the Pumpkin Patch Trolley featured above. Archive photograph from August 2016; this image does not depict the 2026 event. Photo: Kathyradziunas / Wikimedia Commons, CC BY-SA 4.0. Resized for web display; no other changes.
Photo source:
https://commons.wikimedia.org/wiki/File:Johnstown_357_crossing_trestle_at_sunset,_August_2016.jpg
