Highland Park was acquired by the City of Greenfield in June of 1890 for $1,000 from Frank J Pratt Jr. Highland Park is a large property bordered by a residential area and Rocky Mountain Park. Highland Park offers many recreational pursuits including tennis, hiking, mountain biking on some trails, cross-country skiing, and fishing. Highland Park is home to Highland Pond and is bordered by Temple Woods.

The Park offers 4 clay tennis courts. The courts are lined and playable during the tennis season approximately May through October depending on weather conditions. The clay courts are maintained by the Department of Public Works which performs routine maintenance each year. During the off-season, the fenced-in tennis courts are locked to prevent damage to the saturated clay surface.

One water fountain is located on the tennis courts' northwest side. It is operational during the tennis season.
Highland Pond is currently used for summer fishing activities, but some restrictions do apply.

A warming hut that was once used when ice skating was possible on Highland Pond still exists on the property along Parkway Street.

Currently, three formal trails exist in Highland Park. They can be used for various activities including hiking, mountain biking, cross-country skiing, and jogging. Improvements to the trails should be made most critically at the trailheads. The existing sign along Parkway Street is confusing and should be updated. Signage with clearly marked trailheads, destinations, and distances is desperately needed within Highland Park. Additionally, signage for approved and restricted use and park regulations should be visible and inconspicuous.

Members of the Greenfield Tree Committee have put together a walking tour of trees in Highland Park in Greenfield. Take a walking, or virtual, tour of diverse trees located in the 29-acre Highland Park. This approximately 1-mile walk is relatively easy, but wear sturdy shoes for some rocky terrain. To navigate, follow the numbered icons on the map and the corresponding signs on the trees. Please park in the gravel parking area if arriving by car, and look for the first tour sign at the head of the trail to the left of the Highland Park portrait sign and the waste station. Head onto the trail leading uphill (not the trail to the right).

One formally designated parking area is located in Highland Park. It is a gravel surface east of the tennis courts and south of Highland Pond.