Cherokee Park contains many landmarks and points of interest.
Many are self-contained areas within the larger park, set apart from each other by the natural terrain and creative use of landscaping.
Because of the size and design of the park, many events can occur at the same time without interrupting each other.

Big Rock – A large rock in Beargrass Creek, which also lends its name to a picnic area and playground nearby.
The rock itself is used for picnics, and as an ill-advised jumping spot (its flat surface offers about an 8-foot (2.4 m) drop into the shallow creek water below).
There is an open shelter building at Big Rock which was built in 1910 as a memorial to George Gaulbert, it was designed by William J. Dodd.

Scenic Loop – A 2.43-mile (3.9-km) mixed-use road around much of the park, with separate lanes for pedestrians and motorized vehicles.

Frisbee Field – A large open field used for many purposes, most commonly soccer and Ultimate.

Baringer Hill – Commonly called "Dog Hill", "Kite Hill", or "Hill Number One".
Once popular for kites, after a renovation in the late 1990s it has become better known as a gathering point for dog owners.
A fenced dog park located at the top of Cochran Hill opened in 2007.

Hogan's Fountain – A dog- and horse-watering fountain located atop a hill on the Scenic Loop, Hogan's Fountain was financed by the Hogan Family of Anchorage, Kentucky, in 1905.
 The fountain was sculpted by Enid Yandell, and features the Greek God Pan.
It was officially unveiled on August 31, 1905.
The name Hogan's Fountain is also often extended to the nearby hilltop area, which includes a large gazebo, baseball diamond, children's fountains and a basketball court.
This spot was once known as Bonnycastle Hill.
Hogan's Fountain is a popular place for group meetings, family reunions and picnics.

Lover's Lane – A secluded, heavily forested stretch of scenic loop just past Hogan's Fountain.

Cochran Hill – A hillside between Frisbee Field and Lexington Road, and site of a dog park.

Christensen Fountain – A recently restored fountain near the Lexington Road entrance.

Nettleroth Bird Sanctuary – Located in a quiet corner of the park, between Scenic Loop and a residential neighborhood.

Belknap Bridge – When Lily Buckner Belknap died in 1893, her husband Col.
Morris Burke Belknap constructed a stone bridge in Cherokee Park in her honor.
Cherokee Park contains many landmarks and points of interest. Many are self-contained areas within the larger park, set apart from each other by the natural terrain and creative use of landscaping. Because of the size and design of the park, many events can occur at the same time without interrupting each other.
Big Rock – A large rock in Beargrass Creek, which also lends its name to a picnic area and playground nearby. The rock itself is used for picnics, and as an ill-advised jumping spot (its flat surface offers about an 8-foot (2.4 m) drop into the shallow creek water below). There is an open shelter building at Big Rock which was built in 1910 as a memorial to George Gaulbert, it was designed by William J. Dodd.
Scenic Loop – A 2.43-mile (3.9-km) mixed-use road around much of the park, with separate lanes for pedestrians and motorized vehicles.
Frisbee Field – A large open field used for many purposes, most commonly soccer and Ultimate.
Baringer Hill – Commonly called "Dog Hill", "Kite Hill", or "Hill Number One". Once popular for kites, after a renovation in the late 1990s it has become better known as a gathering point for dog owners. A fenced dog park located at the top of Cochran Hill opened in 2007.
Hogan's Fountain – A dog- and horse-watering fountain located atop a hill on the Scenic Loop, Hogan's Fountain was financed by the Hogan Family of Anchorage, Kentucky, in 1905.  The fountain was sculpted by Enid Yandell, and features the Greek God Pan. It was officially unveiled on August 31, 1905. The name Hogan's Fountain is also often extended to the nearby hilltop area, which includes a large gazebo, baseball diamond, children's fountains and a basketball court. This spot was once known as Bonnycastle Hill. Hogan's Fountain is a popular place for group meetings, family reunions and picnics.
Lover's Lane – A secluded, heavily forested stretch of scenic loop just past Hogan's Fountain.
Cochran Hill – A hillside between Frisbee Field and Lexington Road, and site of a dog park.
Christensen Fountain – A recently restored fountain near the Lexington Road entrance.
Nettleroth Bird Sanctuary – Located in a quiet corner of the park, between Scenic Loop and a residential neighborhood.
Belknap Bridge – When Lily Buckner Belknap died in 1893, her husband Col. Morris Burke Belknap constructed a stone bridge in Cherokee Park in her honor.
Cherokee Park