Top 5 Favorites
5. Whitneys Farm Stand, Cheshire MA
This little farm stand is a great way to spend an afternoon. They have a free petting farm and a wonderful play ground with huge wooden vehicles to climb on and "drive." Delicious dairy bar is open seasonally. A top notch garden center, farm market, and bakery. The best time of year for Whitneys is definitely the fall. Their Pumpkin Fest is fantastic! Crafts, live music, tons of pumpkins, haunted corn mazes, bounce houses, tractor hay rides, & lots more!!!
4. Hill Towns
One of our favorite things to do is simply wander the cute, historical towns.
- Start with Stockbridge. Look at Norman Rockwell's Christmas painting of this town and see how its changed since 1967. Stop at the Country Store on Main Street for penny candy and old fashion toys.
- Williamstown is a quaint college town. There are a lot of cute and interesting boutiques and shops to browse- Where'd You Get That is the best!
- The town of Lenox is overflowing with historic homes and cool stores. They have a great green space downtown that is perfect for picnics and frisbee. I feel like someone is always painting, playing the drums, or has a game going on here.
- Finally, Lee has an adorable Main Street to walk. The park at the south end has a gazebo and different fairs every weekend. Make sure to hit Cakewalk Bakery and grab a gourmet cupcake.
3. Berkshire Museum, Pittsfield MA
The priceless art may not impress your young ones, but the Hall of Innovation, Dinosaurs, and Aquarium will! The Hall of Innovation has interactive exhibits to encourage children to be creative. Replicas of dinosaurs, inside and outside, fossils, and a Dino dig let kids step back in time. The Aquarium is on the bottom level. It is small but lets the kids get up close to the animals. It also has a fun touch tank! Do not bring a stroller if possible, the only elevator is old and requires a staff member. Parking is tough in downtown Pittsfield, be prepared to walk. Watch for their special exhibits each summer, they are dynamic.
2. King Cone & Pittsfield Common Park, Pittsfield MA
Local Tip! King Cone has the best and cheapest soft serve ice cream in the Berkshires! However, you would never guess it by looking at the little red shack squeezed in on Fenn St. There is nowhere to sit once you have your delicious snack so walk across the street to the Commons. There is a brand new huge playground, picnic tables, benches, and a paved trail for bikes.
1. Hancock Shaker Village, Pittsfield MA
Fine print: I worked here for 3 years and this is one of my happy places! If you have been to Canterbury Shaker Village in NH, this one is much more extensive, interactive, and kid friendly! Buildings have interpreters (docents), some in costume, who love to share the highlights of each space in age appropriate ways. Take time to look at the special exhibit in the Visitors Center and use the restrooms before you enter the historical village. The entry to the village is a great photo op! Things not to miss when with children:
- Round Stone Barn- make sure you find the hallway in the back to see all the animals and enter the animal fields.
- Discovery Room- the children's hands on room where they can milk a cow, try a craft, and dress up like a Shaker. Baby chicks in the spring!
- School House- cross the street and see the school at the south end. Children can sit in desks, try an ink quill, and see how education was so different 100 years ago.
- Brethren's & Sisters Shops- the yellow buildings show the different jobs the Shakers did based on gender. Often there are demonstrations.
- Brick Dwelling- catch a tour (2x a day) to put this home in context and learn about the basics of the Shakers. Often they also have interactive music programs here too.
- Laundry & Machine Shop- see a demonstration of the working water turbine that powers the Machine Shop.
- Farm & Forest Trail- this one mile trail wanders through the woods and allows kids to run off some energy wile seeing some hidden gems of Shaker history.
Other Highlights
Red Lion Inn, Stockbridge
Opened in 1773, this Inn is filled with found fathers history and antiques.
Tanglewood, Stockbridge
Summer home of the Boston Symphony Orchestra, concerts are kid friendly.
I recommend their Family Fun Fest and Tanglewood on Parade.
Norman Rockwell Museum, Stockbridge
The famous artists collection and his summer studio. Watch for their family programs.
The Mount, Lenox
The home of Edith Wharton. The house is not kid friendly unless there is a special program happening. The gardens are incredible for all ages.
The Clark Art Institute, Williamstown
The permanent collection will return summer 2014 so I don't know what to expect. Before their closure, they had Look Closely cards to engage children, geocaching, sketch pads, and special events that my son always loved.
Mass MOCA, North Adams
This modern art museum will make kids look twice. Take a tour of the Sol Lewitt and try to draw your own!
Mt Greylock, Lanesborough
The highest point in Mass, Greylock has lots of hiking trails of all levels. See Bascom Lodge and go to the top for a breathtaking view.
Jacobs Pillow, Becket
This famous dance festival has inside/out performances that are free and ideal for children. Pack a picnic and enjoy the beautiful grounds.
Pittsfield Suns Baseball, Pittsfield
Formerly the Colonials, the baseball is casual and kid friendly with games and action between innings. Wahconah Park is nice and usually has a bounce house.
Candle Lanes, Pittsfield
You must try candle pin bowling! Plus this little bowling alley is upstairs in historical downtown Pittsfield. Something different to try & explore!
Pittsfield State Park, Pittsfield
Lots of trails, waterfalls, picnic areas, biking trails, and camping. Visit Balance Rock State Park to see a huge limestone boulder balancing.
Ashuwillticook Rail Trail, Lanesborough to Adams
This paved path starts by the Berkshire Mall and runs up Route 8. Its is a beautiful ride as you pass lakes, mountains, and fields!
Colonial Theater, Pittsfield
Host to a variety of wonderful shows, it is just incredible in the inside too!
Lake Onota, Pittsfield
A gorgeous lake, surrounded by the Berkshire hills. Visit Burbank Park off of Valentine Road for fishing, boat launch, picnic area, swimming, and path.
Jiminy Peak, Hancock
Ski resort in the winter and a playground for older children in the summer with its multiple Adventure Parks.
Herman Melville's Arrowhead, Pittsfield
The home of Moby Dick's author. See his inspiration for the novel out the very window where he wrote. Not for young children but great if your high schooler is reading Moby Dick in school!
One of the things I loved about living in the Berkshires is that each week in the summer are music in the various parks and the weekends have festivals in the different towns. Make sure to look in the local paper, the Berkshire Eagle, to find these events during your visit. Here are some of my favorite festivals & events:
- Pittsfields 4th of July Parade
- 3rd Thursdays, Pittsfield
- Ethnic Fair, Pittsfield
- Apple Squeeze, Lenox
- Founders Weekend, Lee
- Hancock Shaker Village Country Fair, Hancock
