Standing in front of Cliff Cave, the namesake feature of Cliff Cave Park, you’d never guess one spot could hold so much history. Peering in through its gated entrance gives onlookers only a vague idea of what lies within.

While there’s no proof all the stories that have been circulated about the cave over the last couple of centuries are true, several have remained fairly unchanged and even documented.

Long ago, Native Americans set up camp inside the cave during hot summer months due to its cool temperature, fresh spring water and the nearby Mississippi River.

Kicking off the cave’s boozey past, French fur trappers used it as a riverside tavern in the 1770s, storing their brews inside. Nearly a century later, Confederate soldiers were said to have met at the cave during the Civil War to discuss strategies.

Once the war ended, Missouri became a landmark for winemaking in the Midwest and the Cliff Cave Wine Company was established. The cave made the perfect wine cellar in the days before electric refrigeration. By 1870, it reportedly had a storage capacity of 100,000 gallons.

The cave continued to attract the attention of imbibers, and in the late 1800s, soldiers from Jefferson Barracks built a saloon there. Anheuser Busch, which owned dozens of caves throughout St. Louis, also leased Cliff Cave for beer storage at one point.

Not only was the cave perfect for stockpiling alcohol, it allegedly held the bodies of victims killed by the mob in the 1920s. What else goes together with the mob and booze? Speakeasies, of course. There were several operated along Cliff Cave Road during that time.

The cave entrance was gated off to the public in 2009 to protect its native wildlife (Indiana bats, large brown bats, eastern pipistrelles, salamanders, isopods) and to safeguard novice explorers from the occasional flash flooding. No structures are left intact, but remnants from the past remain visible in the form of stonework near the entrance.

While the cave’s rich history is fascinating, it’s not what draws most people to the park. Cliff Cave Park consits of 525 acres and is said to be the most naturally diverse park found in the entire St. Louis County system. Since its opening in 1977, three trails suitable for biking, running and hiking have been added.

The Mississippi Greenway is 4.6 miles of looped pavement located in the flood plain wetland area near the Mississippi River. The trail is mostly flat and offers views of the soaring bluffs above as well as barge traffic and native river wildlife, including turkey, fox, rabbits, squirrels, deer and raccoon.

The Spring Valley Trail is 3.75 miles and is located at the front of the park near the entrance to Cliff Cave. This mostly dirt trail consists of two loops, an outer loop and an inner loop, tied together by three, short connector trails that offer a variety of routes for hikers and mountain bikers. The loops vary from compact and twisty to wide and smooth.

The third trail is the Bluff Trail, which is about 1.2 miles and is accessed by going up the park entrance road. This trail has several challenging rock gardens and a stunning view of the river from 170 feet above. Bald Eagles can be spotted from the bluff during winter months.

From downtown, take 44 West toward 55 South until you reach the 255/270 exit toward Chicago. Jump on 255 East and merge onto Telegraph Road. Continue down Telegraph for a few miles and turn left at Cliff Cave Road.

If you’re coming from St. Charles, merge onto 70 East and take 270 South to 255 East and follow the directions above to reach the park. Those coming from Jefferson County should take 55 North to 255 East and pick up where the directions leave off above.

Once you head down Cliff Cave Road, you’ll see several signs leading to the entrance of the park. There are two parking lots: one as you first enter the park near the start of Spring Valley Trail and another, larger lot just beyond near the picnic pavilion and the Mississippi Greenway.

Mississippi Greenway Extension
Cliff Cave overlook
A new, 2-mile trail is under construction, thanks to Great Rivers Greenway and St. Louis County Parks. The new trail will be a paved loop in Cliff Cave Park and will wind up and down the bluffs from an existing trailhead on Cliff Cave Road (fully ADA accessible), where it will connect to a new parking lot and restroom, an overlook atop the bluff, and more miles of trail, possibly extending all the way to Telegraph Road.

Trail Information
Length: All three trails make up nearly 10 miles of pathways throughout the park — 1.2 miles, 3.75 miles and 5 miles
Type: Loops
Surface: Dirt, gravel and paved
Rating: Beginner/intermediate
Best for: Running, hiking and bicycling
Parking: Spring Valley Trail or Mississippi River Trail
Amenities: Parking, picnic pavilion, restrooms, scenic overlooks and handicapped accessible

Heather Ervin is the associate editor of Terrain magazine.