The Trail Names at Smith Park Tell Brentwood's History Out of Order

A rider pulls into the gravel lot off Wilson Pike on a Saturday morning, clips in, and rolls toward the gate behind Ravenswood Mansion without reading the trailhead sign twice. The easy loop is called Kittie's Crossing. It has one short stream crossing, a smooth surface, and a name most people forget by the time they hit the second berm. An hour later, if that same rider has the legs for it, the hardest climb in the whole system waits on the far ridge. It is called Freedom Pass.

Nobody at the gate tells you these two trails are connected. You have to already know, or ride far enough to find out.

The grading system decides what history you meet first

Marcella Vivrette Smith Park's mountain bike system opened in April 2024 on land that was once Ravenswood Farm, with roughly seven miles of singletrack split into beginner, intermediate, and advanced sections. Bike Walk Brentwood worked with the city's Historic Commission to name every trail after a specific piece of the property's past, not as decoration but as the point. Marty Tank, one of the volunteers who pushed the project through, said as much when the gate opened.

"We hope the trails will motivate riders to learn the backstory behind these names."

The problem is that a fitness-based trail system organizes people by ability, not by the order events actually happened. A first-time rider on Kittie's Crossing and a strong rider grinding up Freedom Pass are having the same experience of the same land at the same hour, but the system never puts them in a room together. Most people ride one loop, based on how much climbing they want that morning, and leave without ever meeting the trail on the other side of the ridge that finishes the story they started.

One name at the gate. Fifty-five at the summit.

Kittie's Crossing is a short beginner loop with a stream crossing, named in remembrance of Miss Kittie, one of the enslaved people who lived and worked on the Wilson property. It is the first thing most riders on Smith Park ever pedal.

Freedom Pass sits at the opposite end of both the trail system and the physical effort it takes to reach it. It is the most technically demanding climb in the park, and it honors the 55 enslaved individuals once recorded on that same Wilson property, tracing the difficult route from bondage to freedom in the terrain itself.

Put those two trail markers side by side and a pattern shows up that the grading system was never built to reveal. The entry-level ride carries a single name. The hardest-earned trail in the entire park carries the collective history that name belongs to. A rider who only ever does the beginner loop meets Miss Kittie and stops there. A rider strong enough to reach the black-diamond terrain finishes a story that most visitors to the park never get far enough to see the second half of.

The oldest history in the park sits on the hardest ground

The middle tier carries a different layer entirely. The Raven, Mississippian, and Boiling Spring Schoolmarm are intermediate trails that stretch from Native American heritage to early Brentwood landmarks like the Boiling Spring Academy, one of the community's first schools.

The advanced trail called Stonebox goes further back than any other name in the system. Its off-camber, rocky singletrack was built to evoke the stone-box graves the Mississippian culture left across the region centuries before European settlement. That means the single oldest piece of history commemorated anywhere at Smith Park is also placed on the single most technical stretch of trail, reachable only by riders with the skill to handle it. The deepest past in the park is, physically, the hardest one to reach.

Two more names round out the system once you've climbed enough to see them: Tower Trail, which opens to views of the WSM Radio Tower that has carried the Grand Ole Opry signal for more than a century, and Harpeth Turnpike, a fast descent named for the historic road that once connected Brentwood to Arrington. Every trail in the network funnels back to a central hub called Noble's Corner, named for one of the families tied to the land's early history.

A quick key, roughly by grade:

• Beginner: Hardscuffle Haul (named for Brentwood's historic Hardscuffle community), Kittie's Crossing (Miss Kittie, enslaved on the Wilson property)
• Intermediate: The Raven, Mississippian, Boiling Spring Schoolmarm (Native American heritage through the early Boiling Spring Academy)
• Advanced: Stonebox (Mississippian-era stone-box graves), Freedom Pass (the 55 enslaved individuals recorded on the Wilson property)
• Elsewhere in the loop: Tower Trail (WSM Radio Tower views), Harpeth Turnpike (the old road to Arrington), Noble's Corner (the system's central hub)

None of this is signage trivia. This summer, Mid Tennessee SORBA credited a new Brentwood Rotary Club grant with keeping the trails at Smith Park built and maintained, which means the system is still being actively supported rather than left to age quietly on the map. The names are not a museum plaque bolted to a finished project. They are attached to ground that Brentwood is still choosing to fund.

Fall adds a slower version of the same idea next door

A few miles away, Owl's Hill Nature Sanctuary runs on the opposite pace. The 300-acre sanctuary in northwestern Williamson County has scheduled six Fall Color Hikes for 2026, on October 17, 24, and 31, then November 7, 14, and 21, each one starting at 9:30 in the morning and led by a guide who walks the group through the season's actual progression rather than letting anyone rush it. The series is built for adults and teens, priced at 15 dollars a hiker, and it is the closest thing in the area to reading Smith Park's history at walking speed instead of trail speed.

Owl's Hill closes out its Music in the Meadow concert series on October 3, the last of three shows this year that raise operating funds for the sanctuary's education programs. The season opened back in June with the duo Swan Dive, Bill DeMain and Molly Felder, joined onstage by longtime collaborator Jim Hoke, and it wraps up right as the Fall Color Hikes get underway. Anyone who wants to sit under the actual meadow for one evening before the sanctuary shifts fully into hiking season has one date left to do it.

How to actually read it this year

If the point of naming a trail system after a place's history is for someone to eventually notice, the fall is a fair window to try. A cool morning at Noble's Corner, starting on Kittie's Crossing and working through the intermediate ring before finishing on Freedom Pass if the legs hold up, puts the story back in something closer to the order it deserves, rather than the order a fitness level happens to assign it. Pair that with one of the guided Fall Color Hikes down the road at Owl's Hill, where nobody is grading you on speed, and a Saturday in Brentwood starts to look less like a workout and more like the county quietly showing you what it has been sitting on the whole time.

None of this required going anywhere else. It just required slowing down enough on ground most people already ride past.

If you've lived in Brentwood long enough to have your own favorite loop at Smith Park, or you're still working out which trail to try first, Tricia Gray would love to hear which one you land on. Let's Connect.