Diamond Hill Park
Diamond Hill Park is a former ski slope that is now owned by the town. It features a pavilion, small pond, and a few small fields at the base of the hill that make for a beautiful place to rest after a hike or have a picnic beforehand. It also features spectacular views from the top of the hill.
The trail winds completely around the park. The best route is to go by the pavilion and pond and then across the northern-most field; the trailhead is somewhat hidden at the back of the field. From there it will be a short walk up the hill to the summit, where the views on a clear day are well worth the short hike. Along the way you'll also encounter some of the old equipment from the ski slope and a water tower.
If you continue down the hill the trail will wind all the way to the southern end of the park, then take a sharp right into a swampy area. The trail will then run due north back to the field on the southern side of the pavilion. After leaving the summit there isn't much to see, however, and the terrain is quite rocky in places. If you're interested mainly in the views or have small children with you it may be best to simply hike to the summit and then retrace your steps back to the pavilion.