With a surprise snow storm already in the books, we decided to head out to Stewart Mountain in Chestertown for a fall hike before the trails freeze and it’s time to break out the snowshoes. We were treated to a short, easy climb with views of Loon Lake and distant Gore Mountain.

Stewart Mountain is part of the Chester Challenge, a hiking challenge based in Chestertown. Hikers must visit six of the eight locations to complete the Chester Challenge and receive their pin. Most of the hikes are short and rated as easy or moderate. Some are simple walking trails.

Stewart Mountain is a family friendly, not-quite a mile hike. The trailhead sign suggests a 45 minute trip, but we were up and down in half an hour. Even the most novice hiker will find Stewart Mountain a quick and rewarding climb.

We were greeted by an empty gravel parking lot at the Stewart Mountain trailhead. The day was fifty degrees and overcast, with the occasional blast of strong wind.

The trail begins as a narrow, dirt path with young, looming pines lining both sides. It is well-maintained and clearly marked, with no branches to duck under or logs to trip on. Being early November, most of the .84 mile trail was covered by fallen brown leaves.

Before long, there’s a short incline to a wide open forest that would be perfect for glade skiing. We didn’t leave the trail, as it borders private property, but I imagine this section being a large forest of perfectly spaced trees.

Trail on Stewart Mountain

We reached the summit not long after leaving the wide open path. To the left of the trail is a large rock outcrop that is a perfect spot for lunch. Had it not been overcast, the sun might’ve warmed this spot up for us. Follow the trail downhill for a couple of yards and you’ll find the look out from Stewart Mountain. There’s a sign to the right of the trail that helps to point out the peaks in the distance.

Trail on Stewart Mountain

The view faces west. Gore Mountain and its brown ski trails are in the distance. To the southwest you can spot Crane Mountain, and Hickory Ski Center and Prospect Mountain are to the south. Below the summit is Loon Lake, devoid of boats and surrounded by homes.

After taking a couple of pictures of the far off mountains and Loon Lake, we descended the same trail we had just climbed. On a sunnier day, I would’ve liked to have a sandwich or a snack at the summit. Luckily for us, Chestertown has a keeper in Stewart Mountain, and next time we’ll bring lunch.

Stewart Mountain, Fall