Halloween Train Rides in Connecticut (2026)
At the Connecticut Trolley Museum in East Windsor, the pumpkin patch is an actual numbered stop on the line, station 6A, where historic electric trolleys let kids off to pick a free sugar pumpkin. Six Connecticut rides still have dates on or after October 14: four gentle pumpkin rides and two evening haunted ones. If you live near a state line, our Halloween train finder for the whole country covers the neighbors too.
Trolleys carry a lot of the load here. Besides East Windsor, the Shore Line Trolley Museum in East Haven runs pumpkin trolleys by day and a comedic Bigfoot show on its cars by night. Danbury's railway museum adds a full-size pumpkin train with a storytime version for ages 2 to 5, the Naugatuck Railroad in Thomaston runs a pumpkin train with pumpkin ice cream for one weekend, and Essex has the state's one ride built to truly frighten.
The short version
- Pumpkin and costume rides: Hartford families are about 20 minutes from the Pumpkin Patch Trolley in East Windsor, which runs Friday through Sunday all the way to Nov 1 and gives every child a free sugar pumpkin.
- From New Haven, the Shore Line pumpkin trolley in East Haven is about 10 minutes away, with trolleys to the patch on Oct 17, 18, 24 and 25 only.
- Stamford and the rest of Fairfield County should head to Danbury, about 40 minutes, where the Pumpkin Patch Trains include Saturday storytime departures for ages 2 to 5 and a twilight train every Saturday evening.
- The Naugatuck Railroad's Pumpkin Patch Express in Thomaston, about 40 minutes from both Hartford and New Haven, runs Oct 24 and 25 only and was almost sold out as of Oct 14.
- Haunted rides: The Haunted Trolley in East Haven is the silly one: a comedic search for Sasquatch with early 5 PM shows on Sundays, $29 per person, advance tickets only.
- Tracks of Terror in Essex, about 35 minutes from New Haven and 45 from Hartford, is meant to frighten and is rated PG with parental guidance for under 18; Halloween night showed no online tickets as of Oct 14.
The Naugatuck Railroad's teen haunted train in Thomaston already ran its only date.

Look inside the book
A dark tunnel, a brave corgi. Bring Rally along.
In Rally Takes the Train, a corgi rides into a dark tunnel, gets a little scared, and comes out to a big bright light and happy cheers. It takes about five minutes to read, a good fit for the drive to a Connecticut pumpkin train.
Rally Takes the Train
Eight pages from the book
Turn the page
That's 8 of 25 pages
See who’s waiting at the station
Grandmommy and Papa are at the last stop. Get the full hand-painted book, $13.99 on Amazon.
See the full bookPage 1 of 8
Like it so far? See the full book
25 hand-painted pages, paperback, $13.99 with fast shipping from Amazon.
Every page is real watercolor on paper, painted by hand by Leslie Dunn. Nothing in this book was made with AI.
Compare every Connecticut Halloween train side by side
Every ride on this page in one table: type, dates left, the lowest posted ticket price, ride length, who it suits and whether tickets are still on sale. Tap a ride for the full details.
| Ride | Type | Dates left | Tickets | Length | Best for | Status |
|---|---|---|---|---|---|---|
| Pumpkin Patch Trolley at the Connecticut Trolley MuseumEast Windsor | Pumpkin and costume | Oct 16 to Nov 1 (9 dates) | From $14 | About 30 minutes | All ages, toddlers welcome | Selling out |
| All Aboard the Pumpkin Patch Trolley at the Shore Line Trolley MuseumEast Haven | Pumpkin and costume | Oct 17 to Oct 25 (4 dates) | From $13 | Not posted | All ages, toddlers welcome | On sale |
| The Haunted Trolley, In Search of SasquatchEast Haven | Haunted | Oct 16 to Nov 1 (9 dates) | From $29 | 30 to 45 minute | Older kids who like spooky | On sale |
| Pumpkin Patch Trains at the Danbury Railway MuseumDanbury | Pumpkin and costume | Oct 17 to Nov 1 (6 dates) | From $20 | Not posted | Ages 2 to 5 | Selling out |
| Pumpkin Patch Express on the Naugatuck RailroadThomaston | Pumpkin and costume | Oct 24 to Oct 25 (2 dates) | From $20 | About 1 hour | All ages, toddlers welcome | Selling out |
| Tracks of Terror, Bloodlines on the Essex Steam TrainEssex | Haunted | Oct 16 to Oct 31 (8 dates) | From $49.99 | About 30 minutes | Older kids who like spooky | Selling out |
The rest of October at a glance
When each Connecticut Halloween train still runs
- East Windsor Pumpkin Patch Trolley at the Connecticut Trolley Museum
- East Haven All Aboard the Pumpkin Patch Trolley at the Shore Line Trolley Museum
- East Haven The Haunted Trolley, In Search of Sasquatch
- Danbury Pumpkin Patch Trains at the Danbury Railway Museum
- Thomaston Pumpkin Patch Express on the Naugatuck Railroad
- Essex Tracks of Terror, Bloodlines on the Essex Steam Train
Pumpkin and costume ride Haunted ride Halloween night
Connecticut Halloween train calendar: what runs which day
Every remaining date for every ride on this page, from today through Halloween weekend. Green is a gentle pumpkin and costume ride, blue is a haunted ride. Tap a ride to jump to its details.
- Fri, Oct 16
- Sat, Oct 17
- East Windsor: Pumpkin Patch Trolley at the Connecticut Trolley Museum Pumpkin
- East Haven: All Aboard the Pumpkin Patch Trolley at the Shore Line Trolley Museum Pumpkin
- East Haven: The Haunted Trolley, In Search of Sasquatch Haunted
- Danbury: Pumpkin Patch Trains at the Danbury Railway Museum Pumpkin
- Essex: Tracks of Terror, Bloodlines on the Essex Steam Train Haunted
- Sun, Oct 18
- Thu, Oct 22
- Fri, Oct 23
- Sat, Oct 24
- East Windsor: Pumpkin Patch Trolley at the Connecticut Trolley Museum Pumpkin
- East Haven: All Aboard the Pumpkin Patch Trolley at the Shore Line Trolley Museum Pumpkin
- East Haven: The Haunted Trolley, In Search of Sasquatch Haunted
- Danbury: Pumpkin Patch Trains at the Danbury Railway Museum Pumpkin
- Thomaston: Pumpkin Patch Express on the Naugatuck Railroad Pumpkin
- Essex: Tracks of Terror, Bloodlines on the Essex Steam Train Haunted
- Sun, Oct 25
- East Windsor: Pumpkin Patch Trolley at the Connecticut Trolley Museum Pumpkin
- East Haven: All Aboard the Pumpkin Patch Trolley at the Shore Line Trolley Museum Pumpkin
- East Haven: The Haunted Trolley, In Search of Sasquatch Haunted
- Danbury: Pumpkin Patch Trains at the Danbury Railway Museum Pumpkin
- Thomaston: Pumpkin Patch Express on the Naugatuck Railroad Pumpkin
- Thu, Oct 29
- Fri, Oct 30
- Sat, Oct 31 (Halloween)
- Sun, Nov 1
East Windsor: Pumpkin Patch Trolley at the Connecticut Trolley Museum
Historic electric trolleys carry families out to a pumpkin patch at a stop the museum calls station 6A, where each child picks a free sugar pumpkin, then bring everyone back for fall games. Sugar pumpkins are the small ones, which is good news for a three-year-old who insists on carrying it.
This ride has the longest run left in the state, Friday through Sunday until Nov 1. Fridays run hourly from 10:00 AM to 3:00 PM, and weekends every half hour from 10:00 AM to 3:30 PM, with each ride about 30 minutes. Kids 2 to 11 are $14, and admission also gets you into the Connecticut Fire and Motorcoach Museum on the same campus. Rides go rain or shine, and trolleys can be open to the air, so bring a layer.
Pumpkin Patch Trolley at the Connecticut Trolley Museum at a glance
- Type
- Pumpkin and costume ride: Daytime pumpkin patch trolley, not scary
- Dates left
- Fri Oct 16, Sat Oct 17, Sun Oct 18, Fri Oct 23, Sat Oct 24, Sun Oct 25, Fri Oct 30, Sat Oct 31 and Sun Nov 1
- Tickets
- Tickets on sale for every date through Nov 1 as of Oct 14; the Oct 18 11:00 AM ride was down to 5 tickets. Walk-ins welcome if space allows
- Times
- Fridays (Oct 16, 23 and 30) hourly from 10:00 AM to 3:00 PM; Saturdays and Sundays every half hour from 10:00 AM to 3:30 PM. Arrive 15 minutes early
- Ride length
- About 30 minutes, out to the station 6A pumpkin patch and back
- What's included
- A free sugar pumpkin for each child 2 to 17, fall games, admission to the Connecticut Fire and Motorcoach Museum on the same campus
- Price
- Adults $17; seniors 62+ $16; youth 12 to 17 $16; children 2 to 11 $14; under 2 with a pumpkin $8, under 2 without a pumpkin free on a lap. Prices include a $1 fee; museum members pay less. Refunds or transfers only up to 7 days before
- Ages and scare level
- No minimum age stated; a family fall ride, not scary
- Costumes
- The museum has not posted costume rules; check the operator site No costume? The Rally tunnel tee counts.
- Strollers
- No stroller policy posted; check the operator site
- Parking
- Not posted; check the operator site
- Where
- Connecticut Trolley Museum, 58 North Rd, East Windsor, CT 06088
Tickets on the railroad’s site
East Haven: All Aboard the Pumpkin Patch Trolley at the Shore Line Trolley Museum
The Shore Line Trolley Museum sits near the water in East Haven, and on two October weekends its historic trolleys run out to the museum's own pumpkin patch, with fall-themed activities the museum pitches at all ages. It is the easiest Halloween ride in the state to fit around a New Haven nap: trolleys leave hourly from 11:00 AM to 4:00 PM on most days, and every half hour on Saturday Oct 24.
Adults are $17 and kids 2 to 18 are $13, with infants free. Two caveats: boarding a historic trolley means climbing 2 to 3 steps, and the museum has not said whether a pumpkin comes with the ticket, so read the ticket page before you promise anyone one. Oct 31 is no longer on the museum's schedule.
All Aboard the Pumpkin Patch Trolley at the Shore Line Trolley Museum at a glance
- Type
- Pumpkin and costume ride: Daytime pumpkin patch trolley, all ages
- Dates left
- Sat Oct 17, Sun Oct 18, Sat Oct 24 and Sun Oct 25
- Tickets
- All four dates on sale with every ticket type in stock as of Oct 14. Oct 31 is not on the museum's calendar or ticket system, so check the operator site if you see it listed elsewhere
- Times
- Museum open 10:30 AM to 5:00 PM. Pumpkin patch trolleys hourly 11:00 AM to 4:00 PM on Oct 17, 18 and 25; on Oct 24 every half hour from 10:30 AM to 4:00 PM (no 1:30 PM trolley)
- Ride length
- Not posted; check the operator site
- What's included
- Trolley ride to the museum's pumpkin patch and fall-themed activities; whether a pumpkin is included is not posted
- Price
- Adults $17; seniors $15; kids 2 to 18 $13; infants free
- Ages and scare level
- The museum says fall-themed fun for all ages
- Costumes
- No costume rules posted; check the operator site
- Strollers
- No stroller policy posted; boarding the historic trolleys takes 2 to 3 steps, so check the operator site
- Parking
- Not posted; check the operator site
- Where
- Shore Line Trolley Museum, 17 River St, East Haven, CT 06512
Tickets on the railroad’s site
East Haven: The Haunted Trolley, In Search of Sasquatch
This year's Haunted Trolley show is a comedic Bigfoot hunt staged aboard a historic trolley at the Shore Line museum, and yes, riders meet Sasquatch. It runs at night and carries the haunted name, so we file it with the haunted rides, but the producer calls it completely kid friendly, and all ages are welcome as long as anyone under 16 comes with an adult.
Think interactive theater on rails more than a scare maze: the show runs 30 to 45 minutes, is heavy on comedy, and has no zombies, clowns, chainsaws or actors chasing anyone. The 5 and 6 PM shows are the ones pitched at families. Tickets are $29 per person and sold in advance only, each show is capped at 40 riders, and a few $49 VIP seats board first with a souvenir shirt.
The Haunted Trolley, In Search of Sasquatch at a glance
- Type
- Haunted ride: Evening comedic haunted trolley show, all ages with an adult
- Dates left
- Fri Oct 16, Sat Oct 17, Sun Oct 18, Fri Oct 23, Sat Oct 24, Sun Oct 25, Fri Oct 30, Sat Oct 31 and Sun Nov 1
- Tickets
- On sale for all nine remaining nights with no sold-out dates listed as of Oct 14; each show is capped at 40 riders
- Times
- Fridays 6, 7, 8 and 9 PM; Sat Oct 17 and Sat Oct 31 5, 6, 7, 8 and 9 PM; Sat Oct 24 6, 7, 8 and 9 PM; Sundays Oct 18, Oct 25 and Nov 1 5, 6, 7 and 8 PM. The 5 and 6 PM shows are the most kid friendly
- Ride length
- 30 to 45 minute interactive comedy show aboard a historic trolley
- What's included
- The Sasquatch show on the trolley
- Price
- $29 per person, advance only; a limited number of $49 VIP tickets include first boarding, choice of seats and a souvenir shirt
- Ages and scare level
- All ages welcome; under 16 must be with an adult. No zombies, clowns, chainsaws or actors chasing guests
- Costumes
- Halloween costumes are fine; no other masks or face coverings allowed
- Strollers
- No stroller policy posted; check the operator site
- Parking
- Not posted; check the operator site
- Where
- Shore Line Trolley Museum, 17 River St, East Haven, CT 06512
Tickets on the railroad’s site
Danbury: Pumpkin Patch Trains at the Danbury Railway Museum
Danbury's train makes a 20-minute round trip out to the museum's pumpkin patch every Saturday and Sunday through Nov 1, and what sets it apart is the 11:00 AM Saturday Storytime train made for ages 2 to 5. If your youngest is the reason you are going, book that one, though the Oct 17 Storytime is already sold out.
Every Saturday also ends with a 6:30 PM Twilight Train that comes with a s'mores kit and a campfire, and it rolls back in the dark. Prices come from local coverage rather than the museum: about $20 for daytime, about $25 for twilight, and $23 adult or $21 child for Storytime, so confirm on the museum's page. Online booking closes 6 hours before each train, and walk-ins are welcome.
Pumpkin Patch Trains at the Danbury Railway Museum at a glance
- Type
- Pumpkin and costume ride: Daytime pumpkin patch train with toddler storytime runs
- Dates left
- Sat Oct 17, Sun Oct 18, Sat Oct 24, Sun Oct 25, Sat Oct 31 and Sun Nov 1
- Tickets
- The Oct 17 11:00 AM Storytime train is sold out. Every other departure Oct 17 through Nov 1 had seats as of Oct 14, including the Oct 24 Storytime (about 46 left) and the Oct 31 Storytime
- Times
- Saturdays Oct 17, 24 and 31: 11:00 AM Storytime train, then 12, 1, 2 and 3 PM, plus a 6:30 PM Twilight Train. Sundays Oct 18, 25 and Nov 1: 11 AM, 12, 1, 2 and 3 PM. Online booking closes 6 hours before departure; walk-ins welcome
- Ride length
- 20-minute round trip
- What's included
- Train ride to the museum's pumpkin patch; Storytime trains for ages 2 to 5 on Saturdays at 11 AM; a s'mores kit and campfire on Saturday Twilight Trains
- Price
- Daytime about $20, twilight about $25, Storytime $23 adult and $21 child, per local coverage; the museum has not posted prices, so check the operator site
- Ages and scare level
- Family ride; Storytime trains are aimed at ages 2 to 5
- Costumes
- No costume rules posted; check the operator site
- Strollers
- No stroller policy posted; check the operator site
- Parking
- Not posted; check the operator site
- Where
- Danbury Railway Museum, 120 White St, Danbury, CT 06810
Tickets on the railroad’s site
Thomaston: Pumpkin Patch Express on the Naugatuck Railroad
The Railroad Museum of New England's Naugatuck Railroad runs this hour-long train out of Thomaston along the Naugatuck River, crossing several bridges on the way to its pumpkin patch. Every rider gets a pumpkin plus a dish of pumpkin ice cream from the Nutmeg Fudge Co., which tends to win over the kids who only came for the train.
It runs one weekend, Oct 24 and 25, at 10:00 AM and 2:00 PM, and the booking calendar showed only a seat or two left on each train as of Oct 14. Coach is $20 for adults and kids alike. Cider, soda and snacks are sold on board, and a parking pass is sold separately when you book.
Pumpkin Patch Express on the Naugatuck Railroad at a glance
- Type
- Pumpkin and costume ride: Daytime pumpkin patch train, not scary
- Dates left
- Sat Oct 24 and Sun Oct 25
- Tickets
- Nearly full: the booking calendar showed only about 0 to 2 seats at each of the four departures as of Oct 14
- Times
- 10:00 AM and 2:00 PM
- Ride length
- About 1 hour, with a stop at the pumpkin patch
- What's included
- A pumpkin from the patch and a dish of Nutmeg Fudge Co. pumpkin ice cream; cider, soda, water and snacks sold on board
- Price
- Coach or Premium Coach $20 for adults and children; lounge car $40 adults and $35 children
- Ages and scare level
- No minimum age stated; a family pumpkin ride with no scare element
- Costumes
- No costume rules posted; check the operator site
- Strollers
- No stroller policy posted; check the operator site
- Parking
- A parking pass is sold separately on the booking site; check the operator site
- Where
- Thomaston Station, 242 East Main Street, Thomaston, CT 06787
Tickets on the railroad’s site
Essex: Tracks of Terror, Bloodlines on the Essex Steam Train
This is Connecticut's real scare. The Essex Steam Train turns its night trains into a story-driven haunted ride built around the line "among you is the descendant of a monster." Each visit starts with a group walk-through, then a train ride of about 30 minutes. The railroad rates it PG and requires parental guidance for anyone under 18, and it warns of flashing lights, strobes, uneven ground and dim spaces.
Tickets are $49.99 per person, the priciest Halloween ride in the state, and $10 of that is a non-refundable processing fee. Two Thursdays, Oct 22 and 29, were added. Halloween night has no tickets in the online store, which may mean it is sold out, so check the operator site. Park at the special entrance at 15 Plains Road.
Tracks of Terror, Bloodlines on the Essex Steam Train at a glance
- Type
- Haunted ride: Night haunted train, rated PG by the railroad
- Dates left
- Fri Oct 16, Sat Oct 17, Thu Oct 22, Fri Oct 23, Sat Oct 24, Thu Oct 29, Fri Oct 30 and Sat Oct 31
- Tickets
- Tickets listed for Oct 16, 17, 23, 24 and 30 at all three check-in times, Oct 22 at 6:30 and 9:00 PM, and Oct 29 at 6:30 PM as of Oct 14. Oct 31 has no tickets in the online store and may be sold out; check the operator site
- Times
- Check-in at 6:30, 7:45 or 9:00 PM (Oct 22: 6:30 and 9:00 PM; Oct 29: 6:30 PM only)
- Ride length
- A group walk-through, then a train ride of about 30 minutes
- What's included
- Group walk-through and the haunted train story
- Price
- $49.99 per person, including a $10 non-refundable processing fee
- Ages and scare level
- Rated PG by the railroad; parental guidance required for anyone under 18. Flashing lights and strobe effects, uneven terrain and dim spaces
- Costumes
- No costume rules posted; check the operator site
- Strollers
- No stroller policy posted; check the operator site
- Parking
- Special parking entrance at 15 Plains Road, Essex. Runs in all weather
- Where
- Essex Station, 1 Railroad Ave, Essex, CT 06426
Tickets on the railroad’s site
Already wrapped for 2026
- The Last Stop: A Haunted Train Experience, Naugatuck Railroad, Thomaston: A haunted train for ages 13 and up that ran its single 2026 date on Oct 9.
Rally’s Spooky Train Ride: Halloween shirts
The tunnel page from the book, Rally on his red seat in the dark, is printed on black shirts in sizes for the whole family, from baby to 5XL. Skip the costume hassle: no masks to fog up, no capes caught in the train door, just a shirt that already says Halloween and layers under a coat on a cold platform. A matching set makes for easy pumpkin train photos. See everything in the Rally shop.

Adult tee
Sizes XS to 5XL, black, printed with the tunnel page from the book.

Kids tee
Sizes S to XL, black, printed with the tunnel page from the book.

Toddler tee
Sizes 2T to 5T, black, printed with the tunnel page from the book.

Baby bodysuit
Sizes 3 to 18 months, black, printed with the tunnel page from the book.
Bigfoot on the Trolley or Monsters in Essex: Sorting Out the Scary Part for a Four-Year-Old
The four pumpkin rides are the place to start with little ones: the East Windsor and East Haven trolleys and the Thomaston train run in daylight to a pumpkin patch, and Danbury built its Storytime departures for ages 2 to 5. Nothing about any of them is meant to spook.
The two night rides could not be more different. The Haunted Trolley's Sasquatch hunt is played for laughs, with no chasing and no chainsaws, but a big hairy costume appearing in a dim trolley can still rattle a preschooler, so pick a 5 or 6 PM show and tell them ahead of time that Bigfoot is a grown-up in a suit who is in on the joke. Tracks of Terror in Essex is a different category: the railroad rates it PG, but it is built to frighten, with strobes and dim spaces, so it suits older kids with a parent.

In our book, Rally meets Mr. Conductor, a man in a blue uniform who holds out his hand, and Rally decides this stranger is a friend. If Sasquatch shows up on the East Haven trolley, that is the page I would read in the car on the way: some grown-ups dress up so a trip feels like an adventure. Our Rally and Mr. Conductor coloring printables keep hands busy while you wait for showtime.
Mr. Conductor came from my mom, who imagined all of it, and her part in this book is the heart of it.
How Long the Drive Is to Each Connecticut Halloween Ride From Hartford, New Haven and Stamford
Connecticut is small, but I-95 is not kind on fall weekends; these are approximate times with clear roads.
Drive times, no traffic
- East Windsor
- about 20 min from Hartford; about 55 min from New Haven; about 1 hr 20 min from Stamford
- East Haven
- about 45 min from Hartford; about 10 min from New Haven; about 50 min from Stamford
- East Haven
- about 45 min from Hartford; about 10 min from New Haven; about 50 min from Stamford
- Danbury
- about 1 hr 10 min from Hartford; about 50 min from New Haven; about 40 min from Stamford
- Thomaston
- about 40 min from Hartford; about 40 min from New Haven; about 1 hr from Stamford
- Essex
- about 45 min from Hartford; about 35 min from New Haven; about 1 hr 15 min from Stamford
Shoreline Damp or Inland Chill: Dressing Kids for a Connecticut Trolley in October
Connecticut October afternoons sit in the high 50s to 60s, which feels fine on a daytime pumpkin trolley. Evenings drop into the 40s, and an open trolley car with air moving through it feels colder than the thermometer says. Sunset is about 6:15 PM in mid October, so the Haunted Trolley's 6:00 PM show and Danbury's 6:30 PM Saturday twilight trains both end in darkness, and after the clocks change on Nov 1 it is dark by about 5:40 PM.
The shoreline rides in East Haven and Essex get damp and breezy after dark, so a waterproof shell over the costume helps. Inland, East Windsor and Danbury run a little colder on clear nights. For the daytime trolleys, a hat and a fleece are usually enough.
What Connecticut Museums and Railroads Expect From Families This October
- The Haunted Trolley sells advance tickets only, at $29 each, with each show capped at 40 riders, and anyone under 16 must be with an adult. Do not plan on walking up.
- Essex had no Halloween night Tracks of Terror tickets in its online store as of Oct 14; the added Thursdays, Oct 22 and 29, are the easier nights to get. Note that $10 of each ticket is a non-refundable fee.
- East Windsor is the one pumpkin ride open on Fridays, which helps if you have a preschooler and a free weekday afternoon. Book at least a week out if you might change plans, since refunds stop 7 days before.
- Danbury's Storytime trains are their own Saturday 11 AM departure for ages 2 to 5, and the Oct 17 one is already gone. Online booking closes 6 hours before each train, so a same-morning plan means walking in.
- Thomaston's Pumpkin Patch Express was nearly sold out by Oct 14, and parking there is a separate pass you buy when you book.
- None of the Connecticut operators in our research posted a stroller policy, and the Shore Line trolleys take 2 to 3 steps to board, so bring a carrier.
- Open trolleys are breezy even on a sunny afternoon. Pack hats, and put the costume over a warm layer rather than under a coat nobody will see.
More Pumpkin Rides Over the Line, From the Hudson Valley to the Berkshires
Danbury families are roughly 1 hr 30 min from Kingston, where the Catskill Mountain Railroad's daytime Pumpkin Express runs on Oct 17, 18, 24 and 25 with open flat cars and a patch stop, so if the Danbury dates do not work, our guide to New York pumpkin trains is the next place to look.
Up north, our Massachusetts Halloween train guide covers a pumpkin patch train out of Adams in the Berkshires this year (check the operator site for dates); East Windsor is only about 20 minutes from Springfield, so a lot of western Massachusetts families end up in Connecticut instead. Rhode Island's only ride (see our Rhode Island page), the Railway of Horrors in Chepachet, is a haunted train recommended for 13 and up, and Providence families drive about 1 hour 25 minutes to reach the gentler East Windsor trolley.
A train book for the ride
When your kids want a real intercity train with no Bigfoot on board, our guide to the Northeast Regional along the Connecticut shore is a calmer kind of train day.
Free for train families
Print the Rally coloring pages before you go
Watercolor coloring pages from the book, free to print. They fit in a folder with a few crayons for the line at the depot or the drive home.
Get the free coloring pages for East Windsor
A train story for the ride homeRally Takes the Train is a five-minute rhyming picture book about a corgi's first train trip to see his grand-paw-rents, including one dark tunnel he is brave enough to ride through. Hand-painted in real watercolor. $13.99 on Amazon, for ages 0 to 8.
Buy on AmazonMore for train families
- Halloween train rides in every state: pumpkin trains and haunted rides by state
- Northeast Regional with kids: a different kind of train day
- Every Amtrak route with kids: find a train by city or station
- Halloween books for toddlers for the drive home
Sources
- Connecticut Trolley Museum: Pumpkin Patch Trolley
- The Shore Line Trolley Museum: All Aboard the Pumpkin Patch Trolley
- The Haunted Trolley at the Shore Line Trolley Museum: The Haunted Trolley: In Search of Sasquatch, CT Bigfoot Halloween Adventure
- Danbury Railway Museum: Pumpkin Patch Trains
- Naugatuck Railroad (Railroad Museum of New England): Pumpkin Patch Express
- Essex Steam Train & Riverboat (Valley Railroad): Tracks of Terror: Bloodlines
Checked against each railroad’s own pages and ticket calendars on October 14, 2026. Dates, prices and policies change, so confirm with the railroad before you go.
Connecticut Halloween Train and Trolley Questions, Town by Town
What Halloween events are there for kids in East Windsor, Connecticut?
One family Halloween event in East Windsor is the Pumpkin Patch Trolley at the Connecticut Trolley Museum, a gentle daytime ride on historic electric trolleys to a patch at station 6A, where each child picks a free sugar pumpkin. It runs Fridays to Sundays through Nov 1, with rides of about 30 minutes. Kids 2 to 11 are $14 and adults $17, and admission includes the fire and motorcoach museum on the same campus.
Are there Halloween things to do with kids in East Haven, CT this October?
Yes, the Shore Line Trolley Museum in East Haven has two. By day, All Aboard the Pumpkin Patch Trolley runs to the museum's pumpkin patch on Oct 17, 18, 24 and 25, at $13 for kids and $17 for adults. At night, The Haunted Trolley stages a comedic Sasquatch hunt aboard a trolley on Fridays, Saturdays and Sundays through Nov 1, at $29 per person in advance, with 5 PM shows on Sundays.
What is there to do for Halloween in Danbury, Connecticut with toddlers?
One family option in Danbury is the Pumpkin Patch Trains at the Danbury Railway Museum, gentle 20-minute rides to the museum's pumpkin patch every weekend through Nov 1. The standout is the Saturday 11 AM Storytime train for ages 2 to 5; the Oct 17 one sold out, but Oct 24 and Oct 31 had seats as of October 14. Saturdays also end with a 6:30 PM twilight train with s'mores and a campfire.
Are there Halloween events in Essex, Connecticut for families?
Essex's Halloween train is Tracks of Terror: Bloodlines on the Essex Steam Train, a haunted ride meant to frighten, so it suits older kids more than young ones. It runs Thursdays through Saturdays until Oct 31, starting with a group walk-through and then a train ride of about 30 minutes. Tickets are $49.99. Halloween night had no online tickets as of October 14, so check the operator site.
What Halloween events for kids are in Thomaston, Connecticut?
One family Halloween event in Thomaston is the Naugatuck Railroad's Pumpkin Patch Express, a gentle hour-long train along the Naugatuck River on Oct 24 and 25 at 10 AM and 2 PM. Every rider gets a pumpkin and a dish of pumpkin ice cream. Coach seats are $20 for adults and kids. As of October 14 the booking calendar showed only a seat or two left per train, so book quickly or check the operator site for openings.
Is there a pumpkin patch trolley in East Windsor, CT, and is the pumpkin free?
Yes. The Connecticut Trolley Museum runs historic trolleys to a pumpkin patch at a stop it calls station 6A, and each child 2 to 17 gets a free sugar pumpkin, the small kind a preschooler can carry. Babies under 2 ride free on a lap, or for $8 with a pumpkin of their own. Rides run Fridays through Sundays until Nov 1, so nine dates remain, including Halloween itself.
Which Danbury Railway Museum pumpkin train is best for toddlers?
The Storytime pumpkin train is the one built for them. The Danbury Railway Museum runs it Saturdays at 11 AM for ages 2 to 5, and local coverage lists it at $23 for adults and $21 for children. Oct 17 is sold out, while Oct 24 had about 46 seats as of October 14. The regular daytime trains are short 20-minute rides that also suit little kids.
What are Halloween events for kids near Hartford, Connecticut?
The closest Halloween ride to Hartford is the Pumpkin Patch Trolley in East Windsor, about 20 minutes away, a gentle daytime trolley ride with a free sugar pumpkin on Fridays to Sundays through Nov 1. About 40 minutes west, the Naugatuck Railroad's Thomaston pumpkin train runs Oct 24 and 25 but was nearly full. Older kids who want a real scare can try Tracks of Terror in Essex, about 45 minutes away.
Halloween things to do with kids near New Haven, CT?
New Haven families have the Shore Line Trolley Museum about 10 minutes away in East Haven. Its gentle Pumpkin Patch Trolley runs Oct 17, 18, 24 and 25, and The Haunted Trolley's comedic Sasquatch show runs Friday, Saturday and Sunday evenings through Nov 1. The Thomaston pumpkin train is about 40 minutes away on Oct 24 and 25, and Danbury's pumpkin trains are about 50.
What Halloween train rides for kids are near Stamford, Connecticut?
The closest is the Danbury Railway Museum, about 40 minutes from Stamford, with gentle Pumpkin Patch Trains every weekend through Nov 1, including Saturday Storytime runs for ages 2 to 5. The Shore Line Trolley Museum in East Haven is about 50 minutes away, with daytime pumpkin trolleys on Oct 17, 18, 24 and 25 and The Haunted Trolley's comedic Bigfoot show in the evenings.
Can kids wear costumes on the Connecticut Trolley Museum pumpkin ride?
The Connecticut Trolley Museum has not posted a costume rule for the Pumpkin Patch Trolley, so check the operator site. Elsewhere in the state, The Haunted Trolley in East Haven allows Halloween costumes but no other masks or face coverings. If you do dress up, choose something that fits over a warm layer and lets a child climb aboard a historic trolley easily, since the cars can be breezy.
Is the Haunted Trolley in East Haven too scary for a toddler?
Probably not, but it depends on how your toddler handles costumed characters. This year's show is a 30 to 45 minute comedic search for Sasquatch with no zombies, clowns, chainsaws or chasing. It does run after dark in a historic trolley, and riders meet Bigfoot. All ages are welcome, anyone under 16 must be with an adult, and the 5 and 6 PM shows are the most kid friendly.
Are there still tickets for a Connecticut pumpkin trolley this weekend?
Yes, as of October 14. East Windsor's Pumpkin Patch Trolley had tickets for Oct 16, 17 and 18, though the Oct 18 11 AM ride was down to 5. The Shore Line pumpkin trolley had every ticket type in stock for Oct 17 and 18. Danbury had seats on every train that weekend except the Oct 17 Storytime departure, which is sold out. Check each ticket page before you go.
How old do kids need to be for Tracks of Terror at the Essex Steam Train?
The railroad posts no minimum age; it rates Tracks of Terror PG and requires parental guidance for anyone under 18. It is still intended to frighten, with a monster storyline, a group walk-through, flashing lights and strobes, uneven ground and dim spaces before the roughly 30-minute train ride. At $49.99 per person, think about whether your child enjoys being scared. Younger kids are better off at the pumpkin trolleys.
Which Connecticut Halloween trains run on October 31?
Four Connecticut rides list Saturday, Oct 31. By day, the East Windsor pumpkin trolley runs, and Danbury runs pumpkin trains, a Storytime train and a 6:30 PM twilight train. In the evening, The Haunted Trolley has shows from 5 to 9 PM. Tracks of Terror in Essex lists Halloween night but had no online tickets as of October 14, so check the operator site. The East Haven pumpkin trolley no longer lists Oct 31.
What should kids wear on an open trolley in Connecticut in late October?
Layers, a hat and something windproof. Connecticut afternoons in late October reach the high 50s to 60s, but evenings fall into the 40s, and air moving through an open trolley car makes it feel colder. The shoreline in East Haven and Essex turns damp and breezy after dark, while East Windsor and Danbury get colder on clear nights. Put costumes over a warm layer.
Rally’s Spooky Train RideThe no-fuss Halloween costume
Skip the costume hassle. Wear Rally.
No itchy masks, no last-minute store run, no meltdown on the platform. Pull on the tunnel tee from the book and you are dressed for a Connecticut pumpkin train, warm under a jacket, and matching in every photo.
Who is riding?
Shop the kids tee
Adult
Kids
Toddler
Baby