The grounds are an important part of Hillforest and are probably the best example of 1850s rusticated landscape in the state of Indiana. The site was chosen to give prominence to the house and was an integral part of the total design. The hillside site was integrated into the design of the house and the natural landscape influenced the development of the gardens.
The 56 front steps continue up from Main Street and are encompassed by the circular drive with stone gutters. The brick sidewalk along Fifth Street (called initially Literary Street) is reminiscent of an earlier time. The front entrance originally had a pair of decorative iron gates, which were removed during World War II and sold for scrap metal.
The 10-acre estate was large for the time and was influenced by Italian landscaping and the movement in American architecture led by A J Downing who promoted large naturalistic landscapes. (Hillforest Historical Foundation, Inc. presently owns 6.9 acres). Decorative lawns were seen as a way to embellish and accent architecture. The hillside behind the house had more formal gardens: a pond, gazebo, terraced beds, and the ravines of the landscape influenced the application of a rusticated footbridge and grotto. Above this on the hill supposedly were vegetable gardens, vineyards, and orchards. Outside the side entrance to the house is the melon cellar made of glacial rock, thought to be from Split Rock. Atop the melon cellar is a natural seating area on that glacial rock.
The carriage house, originally three times the current size, burned in May 1970 and was rebuilt in the early 1970s. The original structure probably contained horse stalls, buggy storage, servants’ quarters, a playroom, and a through driveway. A three-hole outhouse or privy was attached to the rear of the building. A greenhouse was located perpendicular to the carriage house at the edge of what is now the upper parking lot and was attached by a roof that covered the driveway between them.
A complex water collection and control system is located on the grounds, possibly consisting of 11 cisterns (7 we have found). The system controlled surface water run-off and maintained a water supply for the house. Also from the roof eaves, some of the water was directed through front porch columns and into a basement cistern.