My brother and I recently headed to October Mountain State Forrest for a taste of fall Berkshire hiking along the Appalachian Trail. We chose to hike the 6ish mile section of the AT between Country Road and Becket Road. This route proved to be a scenic stroll through a classic Berkshire forest with pond views and minimal elevation gain. If you are looking for a walk in the woods, this could be the hike for you.
October Mountain State Forrest is 16,500 acres which makes it the largest state forest in Massachusetts.  Apparently, the park got its name from Herman Melville who lived in nearby Pittsfield. The park features campgrounds, various hike options and is located close to some of the Berkshires key attractions like Tanglewood.
We spotted a car on Beckett road and started our hike from Country road. The AT is always well marked so we had no trouble finding the trail. We warmed up our hiking muscles by climbing Bald Top Mountain which is a very short climb from the trailhead.  Although scenic, there were no views to be had from this 2,060 foot summit. 
We then began traversing towards Beckett road. The trail starts out flat and a little muddy as it follows the outskirts of a swamp. Some trees clung to their green leaves while others had changed to beautiful oranges and yellows and there was a slight chill in the air but the temperature was still pleasant. It was amazing to be witness to the changing seasons in New England as fall began to give way to hints of winter.
October Mountain State Forrest has some ATV trails which were getting plenty of use that day. The growl of ATVs and dirt bikes somewhat diminished from the wilderness experience and ruined our chances of seeing wildlife, but to each their own.  The hike continued to meander through thick Berkshire forest. No other hikers were in sight and it was nice to have the trail to ourselves. I also found it very inspiring to just be on the AT, knowing that so many through hikers had traveled this same trail. 
The terrain changed significantly after passing Finerty Pond. We began the first significant climb as the trail ascended Wailing Mountain (2,200 feet). We found ourselves at the wooded summit after a few sustained pitches. 
There are no real views from here, but the forest is a view in and of itself. The vegetation off the trail is so thick that it looks like your could practically walk on it. From here we moved along a gentle ridge to the summit of Beckett Mountain (2,200 feet).  After that, we had just a short walk down back to our car. The hike only took a few hours so we still had plenty of time to get lunch in Lenox and check out Mass Mocain North Adams.
The Berkshires are a very special and unique place with a charm that must be experienced to truly understand. I highly recommend heading to October Mountain State Park if you are looking for a moderately difficult walk in the woods.