The Berkshires is a mountainous region of western Massachusetts dotted with villages and towns. It is a popular vacation destination with numerous outdoor activities and a thriving arts scene. Come in the Fall as the leaves change colors or in the summer for the renowned Tanglewood Music Festival. You can hike, bike, raft, tube, kayak, and fly through the trees. You can see waterfalls, beautiful gardens, and live theatre productions. Visit wineries, distilleries, museums, and beautiful mansions. Shop and eat in quaint villages and enjoy the beauty that is The Berkshires.
The Norman Rockwell Museum
The Norman Rockwell Museum highlights the life and works of the well-known American artist. Located in Stockbridge – the town Rockwell called home for the last 25 years of his life – the museum features a variety of exhibits displaying the artist’s work, as well as his studio. I recommend going on a tour, in which knowledgeable guides give thoughtful insight into the painter and his artwork. This is an amazing slice of Americana and a significant part of our history.
In Lenox you can eat at Joe’s Diner pictured above in the with the policeman and the little boy. Sit at the same counter and take a pic. Eat a bite. The food is good.
Tanglewood
Tanglewood is a music venue in the towns of Lenox and Stockbridge. It has been the summer home of the Boston Symphony Orchestra since 1937. Running from Mid-June thru late August you can experience classical and pop music in a beautiful setting.
The Mount – Edith Wharton’s House
The Mount was the country home of noted American author Edith Wharton, who designed the house and its grounds. The estate, in Lenox, Ma. is was declared a National Historic Landmark in 1971 and is open to the public. Edith Wharton was an American novelist, short story writer, playwright, and designer. Author of The Age of Innocence, Ethan Frome, and The House of Mirth, she wrote over 40 books in 40 years, including authoritative works on architecture, gardens, interior design, and travel.
Naumkeag House and Gardens
Naumkeag is a Gilded Age mansion offering guided and self-guided tours of the historic house and landscaped grounds. With 44 rooms in the main house and more than 10 acres of gardens designed by Fletcher Steele, Naumkeag offers a delightful way to spend a summer day.
Crane Museum of Papermaking
Take a tour of the Crane Museum of Papermaking and learn about Crane’s ties to the American Revolution, the development of paper for banknotes, and anti-counterfeiting technologies from the 1800s to the future. They have been making the paper our US money is printed on since 1775. They make the paper and ship to Washington DC with lots of armed guards and tracking devices. While you are there you can get your hands dirty and take home a handmade souvenir.
Barrington Stage Company
Barrington Stage Company is a professional award-winning Equity theatre presenting top-notch musicals, masterful classics, cabarets, and youth theater on the Mainstage, the Germain Stage, and Mr. Finn’s Cabaret from May through October as well as a New Play Festival in February. Check their website for dates of upcoming performances. You’ll be glad you did.
Berkshire Mountain Distillers
Berkshire Mountain Distillers has created a line of award-winning spirits including Greylock Gin, Ethereal Gins, Ragged Mountain Rum, Ice Glen Vodka, Berkshire Bourbon, and New England Corn Whiskey. All of these products are handcrafted in their distillery in Sheffield, Massachusetts. Go and tour their brand new distillery where they will guide you through the process from grain to glass or just drop by and taste some samples. Tours on Friday and Saturday. Call to make a reservation.
Balderdash Cellars
Balderdash Cellars is a boutique winery focused on producing ultra-premium wines from grapes grown by world-class California vineyards. Located in Richmond, MA they are open for wine-tasting Saturday and Sunday from 1-5 pm.
Monument Mountain
Hike to the summit of Monument Mountain for views of the southern Berkshires. From the 1,642 ft. summit of Squaw Peak you’ll enjoy views as far away as Mount Greylock and the Catskill Mountains of New York as well as the Hosutanic wetlands and river valley. There are several loop trails to the top with the longest being a 3-mile round trip for a 720-foot elevation gain. Climb on the huge boulders at the summit, enjoy a snack, enjoy the view, and take some great pictures.
Mount Greylock
There is a Visitors Center on the Lanesborough side of the mountain for information about the Mount Greylock State Reservation. There are a variety of trails which rangers at the visitor center can help you scope out. At the summit is Bascom Lodge and the War Memorial Tower. Stay the night at Bascom Lodge or just grab a bite to eat or a drink. Wednesday through Sunday from 4-7 you can enjoy a glass of beer wine by the fire or on the porch while enjoying the view. Ascend the top of Memorial Tower for a 360-degree view. There is a road directly to the top of Mount Greylock.
Ramblewild (Aerial Course)
Also in Lanesborough, MA is the Ramblewild aerial course. You can climb, walk, and zoom high among the trees on eight trails color-coded by level from yellow to double black diamond. The course contains over 100 elements including logs, nets, zip lines, rope bridges, ladders, and tunnels on a self-guided system with clip-in harness. The focal point is a wooden platform from which eight aerial obstacle courses originate. Each course consist of 15-17 elements including high wires, zip lines, balancing logs, rope ladders, cargo nets, and suspended bridges. Ramblewild is one of the top-rated aerial courses in the US.
Rafting/Ziplines/Kayaking/Tubing
Ashuwillticook Rail Trail
The Ashuwillticook Rail Trail is an old railroad track converted into a 10-foot wide paved trail. The trail runs 12.7 miles through the towns of Cheshire, Lanesborough and Adams. Cheshire Reservoir and the Hoosic River offer outstanding views of the scenery and wildlife. Parking lots and restrooms are available at selected locations along the way. The trail is completely paved with places to stop along the away. Pack a lunch from restaurants in Adams or stop along the way. Rent a bike at Village Bike Rental in Adams, MA.
Cascade Waterfall
It is a short walk to the Cascade Waterfall from the downtown areas of North Adams and Williamston. The entire hike takes about an hour and a half and is flat enough for the most inexperienced hiker.
Race Brook Falls
Race Brook Falls is near the Connecticut border off of Route 41 in Sheffield, Massachusetts. It’s a beautiful waterfall that actually has three tiers to it although most people only see one since they can’t hike up the steeper trails or don’t realize the falls goes up farther.
BASH BISH FALLS STATE PARK
The scenic drive to Bash Bish Falls State Park is a year-round delight. From the early-summer mountain laurel in bloom to the blazing colors of fall foliage you will love the drive. A wooded trail leads to the falls, which plunge down a rocky gorge into a deep pool.
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