The Berkshire Mountains in Massachusetts, just south of the White Mountains of New Hampshire, are part of the Appalachian range that stretch from Georgia to Maine. We visited a few of our favorite towns nestled in the mountains, including Lenox and Stockbridge. At the town of Great Barrington, we took a beautiful hike up Monument Mountain.
A yummy, fresh and cool gazpacho was perfect after our hike at the Farm Country Soup restaurant in town. Great Barrington is filled with good food and lots of AT hikers taking a break from the trail.
About an hour south of Great Barrington is Bash Bish Falls State Park in the Taconic Mountains. The park had me at its name and there is the added bonus that it crosses the MA state line and becomes (mid-hike) Taconic State Park in NY. Either entrance has a short and steep tree-canopied hike to the Bash Bish Falls. The rocky gorge leading to the falls is filled with a wide stream of babbling water and on our walk we passed many visitors relaxing on the stones at the water’s edge. The cool falls are a refreshing way to wile away a summer afternoon.
Not far from the Falls we followed winding country roads past farms, orchards and corn fields as we arrived in the town of Millbrook, NY. There is Main Street with antiques, a few restaurants and nice shops. We found an ice cream shop with ice cream from a local dairy and it was great. No pictures of the ice cream, but Samantha’s Sweet Shoppe had great wallpaper and neon. 
Millbrook has a winery that has won several Hudson Valley awards and produces multiple types of grapes and wines, but that is not what drew us to the town. Wing’s Castle is what captured our attention. The Wing Castle was a dream turned reality for Peter and Toni Wing beginning in 1970. The couple inherited the family farm and with imagination and repurposed bricks, stones and wood from the area began building the castle home of their dreams, moat (pool) and all. There are dragon downspouts, a dungeon room, a Buddha fireplace in a common space, stained glass windows and a tower with unobstructed views of three mountain ranges (Catskills, Taconic, and Storm King) and the Millbrook Vineyards and Winery. The project was a constant work in progress until Peter’s untimely death a few years ago. Today, there are daily tours offered and there are several B&B rooms to stay in including a cottage across the street. The grounds are filled with other repurposed items like a cool stone picnic table made from the front step of the former Wing family homestead. The castle was created as a labor of love and it shows. The cottage, where we stayed, looks out on a huge lily pad-filled pond. The frog serenade was endearing and a perfect soundtrack for the evening.
Wine in sight, we made our way to the vineyard and explored the plentiful NY Hudson valley offerings including chairs made from old wine barrels. 
Ice cream, waterfalls, a castle and wine; what a wonderful day.
Where is Wendy 