Go swimming and have a picnic at Mount Tom, then hike the trail to the stone lookout tower for some memorable views.
Loring S. on Mount Tom Tower Trail
This is a cool place to visit. We loved the tower and a few other things about this place. Check out our full write up.
This is a nice short trail with an approximate elevation gain of 395 feet and the reward of a great view at the top off of an old stone tower. The trail is very rocky in some parts, so you should wear appropriate shoes to protect your ankles. The blazes (yellow blobs of paint) are somewhat spread out, but the trail is relatively easy to follow. Some parts of the trail are covered by debris (e.g. a fallen tree). People have created mini-trails that circumvent those areas. Because there are other trails that do not appear to be marked, pay close attention to the yellow blobs of paint -- particularly when you are nearing the end where an arrow of paint points you downward, yet the trail looks like it continues. Overall, an enjoyable hike.
This mountain, one of the mountains in the Mt. Tom range (the other Mt. Toms being in Moodus, CT and Holyoke, MA) has a few different trails. The trail that begins near the parking lot is the easier of the two that lead to the lookout tower. If you walk down the road towards the pond another trail is marked and leads to the tower as well, connecting to the aforementioned easier trail. The latter trail is a bit more demanding.
Although the tower is closed for repairs now, I pretty much grew up hiking this trail and can say that it is worth the trip any time of year. Right now the foliage is amazing.
Today I discovered another trail but it is not marked with an obvious sign like the other trails, so I'll let you discover it for yourself!
Very beautiful, great swimming in the summer, too. I've been told that you can see Long Island with binoculars on a clear day, but even without binoculars the view is spectacular.