The Perfect
Family Adventure
All aboard for a railroad-themed getaway in southeast Missouri. The Iron Mountain Railway in Jackson, Missouri, is a nostalgic train ride experience just about 45 minutes from The Caboose Roost — making it a perfect day trip for guests who love trains, history, and small-town adventure.
After your train ride, continue the railroad experience with an overnight stay inside our authentic restored 1958 caboose. It’s a fun and memorable pairing for families, couples, and train enthusiasts looking for something truly different.
Junior Conductor Sets
Iron Mountain Railway rides require reservations, so be sure to check their schedule before your trip. Then book your caboose stay and turn your train ride into a full railroad-inspired getaway.
Train rides begin in April,
this is the schedule for the rest of 2026.
August
August 15- Saturday 1pm- Iron Mountain James Gang Robbery
August 22- Saturday 1pm- Iron Mountain James Gang Robbery
August 22- Saturday 6pm- Evening Chuck Wagon
August 22- Saturday 6pm Evening Sunset Train Ride
August 29- Saturday 1pm- Iron Mountain James Gang Robbery
September
Sept 5- Saturday 1pm- Scavenger Hunt Train/Iron Mountain James Gang Robbery
Sept 5- Saturday 6pm- Evening Pizza Train
Sept 12- Saturday 1pm- Iron Mountain James Gang Robbery
Sept 19- Saturday 11am- Iron Mountain Anniversary-Iron Mountain James Gang Robbery
Sept 19- Saturday 2pm- Iron Mountain Anniversary-Iron Mountain James Gang Robbery
Sept 26- Saturday 11am- Pioneer Day-Iron Mountain James Gang Robbery
Sept 26- Saturday 2pm- Pioneer Day-Iron Mountain James Gang Robbery
October
Oct 3- Saturday 1pm- Pumpkin Patch Train
Oct 4- Sunday 2pm- Pumpkin Patch Train
Oct 10- Saturday 1pm- Pumpkin Patch Train
Oct 11- Sunday 2pm- Pumpkin Patch Train
Oct 17- Saturday 1pm- Pirates and Princesses
Oct 17- Saturday 6pm- Evening Murder Mystery
Oct 24- Saturday 1pm- Chocolate Express/Iron Mountain James Gang Robbery
Oct 25- Saturday 2pm- Scavenger Hunt/Iron Mountain James Gang Robbery
Oct 31- Saturday 1pm- Halloween Express
November
Nov 1- Sunday 1pm- Fall Foliage Tour
Nov 7- Saturday 1pm- Veterans Day Train/Iron Mountain James Gang Robbery
Nov 8- Sunday 1pm- Fall Foliage Tour
Nov 14- Saturday 1pm- Searching For Big Foot
Nov 15- Sunday 1pm- Fall Foliage Tour
December
Enjoy the most magical time on our Christmas Train. Filled with fun, enjoy the antics on the Iron Mountain as our Christmas special guests attempt to land Santa on our moving train. If we are successful, you will get to visit with him too! Games, songs, fun and Christmas magic fill this train to the brim. Our volunteers work very hard to make sure this is an amazing time!
2026 Santa Trains are sold out.
Tickets will go on sale in January 2027 and will sell out in a few short hours.
Check the website or call for details.
573.243.1688
Plan Your Iron Mountain Railway Adventure
Make it a Railway Weekend
Your Weekend Itinerary, planned
Friday
-
Check into The H&R Caboose Roost
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Dinner at The Depot in Fredericktown
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Relax by the firepit & enjoy S'mores
Saturday
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Breakfast in Fredericktown
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Drive to Jackson
-
Ride the Iron Mountain Railway
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Return to the caboose for yard games and fun
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Roast hot dogs at the firepit
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Read train books to the kids at bedtime in the roost
Sunday
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Coffee on the caboose platform
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Visit Castor River Shut-Ins, Elephant Rocks or Silver Mines before heading home
Ride a Railcar,
Sleep in a Railcar
Built in 1958, this authentic caboose has been thoughtfully restored while preserving the character that made it special. Inside, you'll discover vintage railroad artifacts, historic photographs, books, and carefully curated details that celebrate the golden age of railroading.
The caboose's name also tells a story. H honors Harry, a longtime Terminal Railroad Association of St. Louis (TRRA) engineer and my dad, whose career on the railroad inspired this dream. R honors Rick, a dear friend and the caboose's previous owner, who originally purchased the caboose and brought it to Fredericktown. Rick's dream was to restore and live in the caboose, but unfortunately never had the chance.
Whether you've spent a lifetime around trains or you're simply discovering their charm, you'll find countless details that make this stay unlike any ordinary vacation rental.
After riding the historic Iron Mountain Railway, there's no better way to continue your railroad adventure than spending the night in a caboose with a story of its own.
Why Train Enthusiasts Love Staying Here
Rock Island &
Chicago Northwestern
Memorabilia
Frequently Asked Questions
How far is The H&R Caboose Roost from the Iron Mountain Railway?
The H&R Caboose Roost is located in Fredericktown, Missouri, approximately 45 minutes from the Iron Mountain Railway in Jackson, making it easy to enjoy both experiences during one memorable southeast Missouri getaway.
Do I need reservations for the Iron Mountain Railway?
Reservations are recommended, especially for popular excursions and special events. Check the railway's current schedule and ticket availability when planning your trip.
Is the Iron Mountain Railway good for families with children?
Yes! A historic train ride can be a fun and memorable experience for both children and adults. Pairing your train ride with an overnight stay in a real caboose makes the adventure even more exciting for young train lovers.
Can I ride the train and visit other attractions in the same weekend?
Absolutely. Make the train ride the centerpiece of your trip, then explore other southeast Missouri attractions such as Elephant Rocks State Park, Silver Mines Recreation Area, or one of the area's scenic hiking destinations.
Where can I stay near the Iron Mountain Railway for a unique railroad experience?
For train enthusiasts looking for something beyond an ordinary hotel, The H&R Caboose Roost offers an overnight stay in an authentic 1958 railroad caboose. Inside, you'll find railroad artifacts, photographs, books, and curated pieces of railroad history alongside modern comforts.
Can I make the Iron Mountain Railway and caboose stay into a weekend getaway?
Yes! Spend the day enjoying a historic train ride in Jackson, then continue your railroad adventure with a stay at The H&R Caboose Roost. It's a fun way to create an entire weekend around railroad history while exploring southeast Missouri.