On The Rails & On The Trail
Things to Do
in Fredericktown, Missouri
Make The H&R Caboose Roost your home base for memorable days on the rails, scenic trails and some of Southeast Missouri’s most remarkable outdoor adventures.
The Caboose Experience Starts Here
You don’t have to leave the tracks to make unforgettable memories. Sip coffee on the caboose platform, challenge the family to a round of yard games, or simply slow down and enjoy the peaceful surroundings.
As evening arrives, gather around the private firepit beneath the café lights, roast marshmallows and settle into a slower pace of life at The H&R Caboose Roost.
-
Lawn Games & Entertainment – Badminton, croquet, yard dice, bean-bag toss, frisbee
-
Outdoor Living – Private fire pit and outdoor seating
-
The Perfect Launchpad – Unwind in our backyard oasis, then head out to explore the best of the Missouri state parks just minutes away.
Rainy Days on the Rails
When the clouds roll in, the adventure doesn’t stop—it simply gets cozier. Settle into the vintage charm of the caboose with games, books, hot cocoa and the peaceful sound of rain against the steel roof.
-
Vintage Board Games & Train Trivia – Unplug and gather around the table for a classic family game night or a friendly trivia championship.
-
The Ultimate Reading Nook – Climb up into the conductor's cupola loft with a good book, watch the rain sweep across the tree line, and relax in your own private getaway.
-
Movie Night & Hot Cocoa – Slip into a signature bathrobe, stream a movie and enjoy a slow, cozy afternoon.
JUST MINUTES FROM THE CABOOSE
Explore
Fredericktown, Missouri
Spend a little time exploring historic downtown Fredericktown, where locally owned restaurants, coffee shops and small-town stops surround a courthouse square shaped by more than two centuries of mining, railroad and community history.
A Remarkable Courthouse Square
At the heart of downtown is the Lancaster-plan courthouse square and the historic Madison County Courthouse, built in 1900. It was designed by renowned architect Theodore C. Link, best known for designing St. Louis Union Station. The courthouse and surrounding commercial district are listed on the National Register of Historic Places.
A Town Built on Mining & Railroads
Fredericktown grew near one of Missouri’s earliest lead-mining regions. Mining, trade and the arrival of the railroad helped shape the community, while its two historic railroad depots preserve another chapter of the town’s transportation story.
Dine in a Historic Train Depot
Continue the railroad experience with lunch or dinner at The Depot Cafe, located inside Fredericktown’s beautifully preserved 1917 Missouri Pacific Railroad Depot. Once a working passenger station, the historic building is now known for its welcoming atmosphere and made-from-scratch meals—and is listed on the National Register of Historic Places.
Dinner, Delivered to Your Caboose
Stories From the Civil War
Fredericktown was also the site of the Battle of Fredericktown on October 21, 1861. This Civil War engagement helped the Union secure control of Southeast Missouri and remains an important part of the area’s history.
Local Flavor
After exploring downtown, stop for coffee, enjoy a relaxed café breakfast, browse local shops, or settle in for dinner before returning to the caboose.
EXPLORE NEARBY
State Parks, Scenic Trails & Railroad Adventures
From remarkable rock formations and rushing rivers to scenic trails and historic train rides, some of Southeast Missouri’s most memorable adventures are within easy reach of the caboose.
Elephant Rocks State Park
Massive granite boulders, perfect for climbing, exploring, and photos.
-
30 minutes from the caboose
-
Great walking trails
-
Perfect for families
Pickle Springs
Natural Area
If you love scenic hikes, unusual rock formations, and the feeling of discovering something truly special, Pickle Springs Natural Area is worth the drive during your stay at The H&R Caboose Roost. Often described as one of the most beautiful hikes in Missouri, Pickle Springs is a natural wonderland of sandstone bluffs, narrow canyons, waterfalls, rock formations, and lush forest scenery—all packed into a relatively short trail.
