
Introduction
I never would have guessed that I’d be training for my next trail race right in the heart of Rochester, New York — but that’s exactly what happened when I stumbled upon the Pinnacle Hill Trail on Field Street.
Exploring Pinnacle Hill Trail in Rochester
Tucked away behind a small trailhead entrance on Field St., the Pinnacle Hill Trail offers a scenic and surprisingly challenging run or hike through one of Rochester’s best-kept secrets. The trail system winds its way up Pinnacle Hill — formerly known as Mount Monroe — and even includes land that once belonged to St. Patrick’s Roman Catholic Cemetery.
Despite its urban location, this trail feels tucked away from the city. If you follow the path on the right side of the hill, you’ll eventually reach the highest natural point in Rochester, which rewards you with an amazing view of the Bristol Hills. From the top, you can also see the iconic radio antennas that mark the summit and are visible from nearly anywhere in the city.

Trail Tips: Hiking or Running Pinnacle Hill
If you’re hiking or trail running from the Field Street entrance, I recommend staying to the right-hand side of the trail system. These trails are designated for foot traffic and provide a steady, scenic climb. The left side is mostly used by mountain bikers, and sharing that space can get tricky.
Once you reach the summit, you have two options:
- Turn around and return the way you came
- Continue down the single-track trail that leads to the Hillside Children’s Center Visitor Entrance on Pinnacle Hill Road

Trail Stats and Final Thoughts
Since discovering this hidden trail, I’ve made it a regular part of my running route around Rochester. The climb to the top is about 0.25 miles with approximately 170 feet of elevation gain, making it a great hill training segment for runners or a quick challenge for casual hikers.
Whether you’re a trail runner in Rochester, a local looking for new hiking spots, or someone training for a race, the Pinnacle Hill Trail is definitely worth a visit.