Although there are many bucolic areas in New England, only the Berkshires can boast spectacular hikes, revered art collections, Gilded Age architecture, and internationally acclaimed performances, and a great local food scene to enjoy all in one day.
See our Guide for the 8 most luxurious Berkshires house rentals for families!
Where are the Berkshires and why visit them?
The Berkshires is the collective term for the Western-most area of Massachusetts and is equidistant to New York and Boston by car. It is a region to visit over several days, like Napa or the Cotswolds, or Puglia. The eastern-most edge of New York State’s Columbia County has become part of the Berkshires over time, so it’s likely you will cross state lines a few times during a visit.
The Berkshires has been a very special destination for me— one I have visited almost yearly since 1986 when I started summer camp in Lenox.
When to go to the Berkshires
For the peak cultural experience, explore the Berkshires from the last week of June through Labor Day, as all of its performing organizations will be in full swing. Towards the end of July, most of the area summer camps will offer a visiting weekend, and all area accommodations will book up early. It’s the one time of year Manhattan’s wealthiest who don’t plan ahead will secure two-star motel rooms with a smile.
If you are more outdoorsy or want the scenic fall foliage experience, the first two weeks of October are best. Although we typically visit in the summer, to experience the Berkshires is pure fall foliage bliss.
The Best Hotels in the Berkshires for every occasion
All-out Luxury Berkshires Hotels
Lenox highlights two of the most luxurious small hotels in New England. First Blantyre is where you go for extremely formal service to recreate the Gilded Age history of the area. This historic estate is modeled after a Scottish property and is a member of Relais & Châteaux’s prestigious list of deluxe Epicurean destinations.
Blantyre has a pretty firm no-child policy. It’s a perfect adult-only escape for those couples who find Masterpiece Theatre a turn-on. Families don’t stay there until their youngest children reach the age of sixteen except for weddings and events that have taken over the property.
There is a formal restaurant for dinner, but we tend to prefer the lunch restaurant and its beautiful space with views of the grounds. The hotel just updated all of their rooms to the horror or delight of its regulars. Gone are the antique furnishings that gave each room its own personality like a true home.
Wheatleigh offers the other spectrum of a luxury experience. It is sleek and modern and the opposite of fussy, contrasting its spectacular Italianate exterior. It’s European staff offer fantastic service a few hundred yards away from Tanglewood. Its formal French restaurant is one of our favorites in the US.
Wheatleigh has no such policy preventing children, but it wouldn’t be my first choice if traveling with more than one child, unless they were both over twelve. It’s a very stylish and elegant atmosphere, and the staff will offer an iPad loaded with kids’ movies to provide some in-room or dining room entertainment. We enjoyed how spacious the rooms are, and the French accents of the staff made us crave croissants at breakfast.
Wheatleigh is best enjoyed by families during their summer outdoor barbecue (usually scheduled for Wednesdays) or in their more casual restaurant for lunch. Our children enjoyed lawn games with new friends and found plenty of food they enjoyed in the buffet.
Full-Service Berkshire Resorts and Spas
The best option for an authentic Lenox cottage experience with the kids had been Cranwell Resort and Spa, which has suites and junior suites perfect for families, an indoor pool, and other on-site recreation. But Hyatt’s Miraval brand is presently transforming the property into Miraval Berkshires, to rival Canyon Ranch down the street.
Canyon Ranch is one of our favorite places on earth. I hosted Luxe Recess’ first parenting retreat there in the Fall of 2019.
Though guests must be at least fourteen years of age, we don’t really go to Canyon Ranch to leave property. It’s a destination spa that will truly elevate your well being with excellent instruction on nutrition, cooking, movement, and complementary medicine.
Spa treatments are wonderful, and guests feel comfortable to wear their robes to dinner after massages. They do serve wine and beer with dinner if you ask, but it is really a place for those serious about improving their health and habits from top to bottom.
Luxe Recess can book Canyon Ranch stays with many extra amenities and resort credits for your stay.
See our Guide for the 8 most luxurious Berkshires house rentals for families!
Other Berkshires Hotels of Note
The Williams Inn, The Best Choice in Williamstown
The most recent, noteworthy opening in the Berkshires is the Williams Inn. It’s situated adjacent to Spring Street, the Williamstown run of retail and restaurants. Visitors of the Williamstown Theater Festival, the Clark Art Institute, and Williams College now have a high-end option for sleeping.
Paying homage to the Williams College purple, the rooms are tastefully a nod using a gray-based light mauve for the walls, a deeper gray purple sliding barn door to separate the marble bath from the rooms, and purple and ivory linen curtains and bolster pillows.
The Williams touch isn’t overt unless you open the closet to see a tenant hanging on the wall. Each of the three floors of rooms have a beverage station for staying sustainable. Guests can use locally-crafted mugs at the coffee machine or the purple glasses for still or sparking water.
Beds, robes, and pillows showed nice cozy quality, and the windows had track night shades. My favorite touch was a small compass with “The Road Less Travelled” by Robert Frost scripted inside its cover. This was a charming detail that many might overlook on the desk.
Families can book connecting rooms with a king in one and two queens in the other. These are limited in inventory, so book ahead for peak times. For families larger than four, king suites have a parlor in between two king bedrooms, and the parlor can take a rollaway bed.
The Barn is the on site restaurant with its wood beams and staff dressed in denim aprons and jeans. My kids enjoyed the lemon ricotta pancakes. Order anything with skillet in the title, whether it is the breakfast skillet or brownie s’mores skillet for dessert. They make a mean burger, and we devoured the parmesan fries with truffle aioli.
We sat in their library and game area off the lobby playing Clue, one of the numerous family games for guests before our dinner reservation while we saw other families take glasses of Prosecco to their patio and fireplace. There’s now a great choice for those seeking accommodation to match the cultural and academic offerings of Williamstown.
The North Adams Option: Porches Inn
The Porches Inn (read our full review) is our other family favorite for places to stay in the northern section of the Berkshires. It offers a free breakfast and outdoor pool that remains open year-round. While it lacks room service, it offers a parlor for games and a walkable distance to Mass MoCA and its many dining options. The Porches Inn is across the street from the Mass MoCA.
The Vacation Village in the Berkshires and the Wyndham at Bentley Brook are standard timeshare style resorts offering one or two bedrooms, full kitchens, and family activities. They are not stylish or luxe and are outdated in their furnishings, but they offer family activities and easy access to the ski lift and outdoor park at Jiminy Peak.
Other Gilded Age Mansions Converted to Inns
Right in Lenox, the Kemble Berkshires stands out. We personally try and avoid that country floral style when booking inns and bed and breakfasts. It’s just not sexy. Fortunately, the Kemble Inn delivers exactly what we like. Purchased and restored by a Canadian financier who always wanted to own his own Gilded Age Mansion, The Kemble Inn is decorated vibrantly and skillfully in Ralph Lauren, a perfect fusion of his British Colonial and Art Deco furniture collections.
Some rooms contain sleeper sofas for families, and a third floor room not as luxuriously appointed also welcomes families. There is a restaurant on-site serving breakfast included in the rate, as well as, dinner offered a la carte. The dining room walls are covered in portraits of Queen Elizabeth and other Berkshire cottages: The Mount, Blantyre, and Ventfort Hall.
The Seven Hills Inn is a Gilded Age home with a motel building on property. It’s perfect for those wanting to be near everything without resorting to budget motels along Route 7. It underwent a grand scale room renovation in 2019. A simple pool rests at the foot of its back yard. A bountiful breakfast buffet is included in the rates.
Hotel Chains in the Berkshires
Marriott and Hilton have properties along the main routes in the Berkshires, too. These work well with their complimentary breakfasts and onsite pools, but they come at premium rate, often around $300 per night during high season. Standouts include the Fairfield Inn Berkshires, The Courtyard Marriott Lenox Berkshires, The Hilton Garden Inn Lenox.
What to Do and Where to Eat in the Berkshires
Great Barrington
Great Barrington is the largest town in the southern Berkshires and has a large pedestrian-friendly Main Street with shops and restaurants. For our trips, it has always been more of a base for eating and shopping than staying overnight.
For us, we see it as the home of Baba Louie’s, an artisan pizza shop that offers Neapolitan style thin crust pizzas that can be customized for any food allergy. The gluten-free crust is as good as gluten-free pizza can be.
Robin’s Candy is a novelty shop filled with fun gifts to browse while you wait for your table at Baba Louie’s next door. But SoCo Creamery is just a few steps around the corner, and although the company has been sold to a larger maker since it was founded, every chocolate lover must try Dirty Chocolate just once. If you live in the Boston area, you can get your fix at Roche Brothers supermarkets.
I withhold our verdict on Bistro Box as we made the drive south of town for this seasonal takeout that my local contacts rave about only to see that they were closed. Based on the menu, we’ll be back, as it looks to be worth the hype.
West Stockbridge
West Stockbridge is another foodie destination and where to head for your first or last meal of the day.
Depot 6 is a coffee house that roasts its own coffee and offers full breakfast in addition to bakery treats. The place is popular, so expect waits at peak times. The most child-friendly options are the waffles, eggs, and bakery treats. Their sandwich and salad options are too sophisticated for most kids to enjoy.
I must have ordered the wrong type of coffee. I asked for their darkest roast blend called the Heart of Darkness. It tasted off to me, but the place was so inviting, I’d be happy to give them a second try.
Rouge has been a staple restaurant in the community for fifteen years, and we had an excellent dinner with our kids in the bar area where it seemed a better fit than the more romantic and adult atmosphere of the restaurant.
Maggie, the owner, brought an incredibly useful tub of magnetic building toys for my son to play with while we enjoyed the house specialties of duck confit, shitake spring rolls, serious burgers, truffle fries, and a massive vegetarian platter that could have fed Peter Rabbit and his family for the entire winter.
Stockbridge
Stockbridge offers three classic Berkshire attractions: The Norman Rockwell Museum, The Berkshire Botanical Garden, and Naumkeag, a restored Berkshire cottage with magnificent gardens and views.
The Norman Rockwell Museum is the least family friendly on this list, but if you are visiting the Berkshires on a multi-generational trip, it is a must do. The museum offers temporary exhibits of other illustrators, and sometimes those can be engaging to children.
The Berkshire Botanical Garden is a fantastic family experience for those with toddlers and preschoolers. We loved, when our kids were young, to let them loose in the garden and explore at their pace. For older kids, the fall fest is its big annual event for families.
Naumkeag, the former estate of the Choate family, is a historic residence managed by the Trustees of the Reservation. It offers a child’s guide, scavenger hunt, and outdoor gardens with spectacular views behind the property. The Asian garden was fully restored this season, though young kids won’t find it particularly interesting.
Visitors tour the home with a guide, but it is short enough to keep the attention of most kids. If you think your kids aren’t up to it, take turns enjoying the gardens with them while the other explores the house.
Lenox
Most visitors to the Berkshires arrive during the Tanglewood season of the Boston Symphony Orchestra, from late June until Labor Day weekend. Tanglewood’s appeal for families is that all concerts in both the main music shed or smaller music hall can be enjoyed on picnic blankets with lawn tickets. While children may find the standard performance difficult to enjoy for up to two-and-a-half to three hours, infants and young children can easily fall asleep on the laps of parents.
There is a family concert event one day in the summer that offers an excellent “instrument petting zoo” to give children a chance at playing various instruments, as well as, crafts, and a family friendly concert. There is also a movie-themed performance during the summer that plays a soundtrack such as Raiders of the Lost Ark which is a great introduction to Tanglewood for families.
Preparing a picnic can feel like a competitive sport when you see some of the other attendees and their elaborate spreads.
Ventfort Hall is a best known for serving as the orphanage in the film adaptation of The Cider House Rules, and is slowly being restored while serving as the Museum of the Gilded Age. There are some family-friendly programs, but the appeal to visit is really for those who have a passion for historic preservation and restoration. My husband and I split up to tour while the other takes the kids to the back porch and lawn to play.
My favorite road to drive in the entire country is Undermountain Road in Lenox. Start driving across from the main entrance to Tanglewood, and you’ll pass Stoneover Farm on your left. This is a great bed and breakfast for families if you can secure the Schoolhouse Suite. There is a barn that has been converted into gallery space, and children will love observing the ducks in the pond.
You’ll pass the Undermountain Farm and a magnificent view in any season, and the road will become Cliffwood Street that will being you back to Lenox’s historic town center.
The Best Lenox Restaurants
We love Haven, a bakery and café that offers delicious food with many gluten-free options and decadent desserts and cocktails. The wax paper-lined chocolate cake is incredible, simple, and tough to improve. Haven is very popular, and serves only breakfast and lunch. The omelettes and soups are particularly good.
For more formal sit-down lunches and dinners, we love Alta Wine Bar which is one of the most popular venues that requires reservations (taken for dinner only) or early or late arrival during weekend lunches.
Bistro Zinc down the street is a strong option, too, particularly with great bistro fries to enjoy with mussels or steak frites. Brava is a small wine bar known for its wood-fired pizzas and tapas. They don’t take reservations, so join the savvy diners who line up at 5:00 PM when the restaurant opens to grab a table.
There are many desserts worth having in Lenox. Head to Chocolate Springs north of the town center on Route 7. It offers, pastries, chocolates, gelatos, and sorbets well worth the trip.
In town, the The Gifted Child offers toys on its first floor, clothing and baby gear on the second floor, and a sale barn behind the main building. I’ve never found anything I would want to buy in the barn, but my kids always find toys to buy. The clothing is more for visiting grandmothers than local families.
Our family’s favorite Lenox destination is The Mount, the estate of writer Edith Wharton. The gardens are magnificent, and the grounds surrounding the home often have art installations to enjoy amidst the shaded stretches of ferns.
Ghost tours and jazz concerts are some of the many programs for families. During this visit, we observed the Berkshire Coaching Weekend, the tradition of driving the original coaches in period costume from the Elm Court Estate to the Mount.
Pittsfield
Pittsfield is the largest city in the Berkshires but doesn’t possess a concentration of the area’s attractions. Its economic struggles from the closing of nearby factories persists today, though there’s a sign of economic revitalization on the town’s main strip, North Street, not far from the Berkshire County Museum which is both a natural history and art museum with a section for children with hands-on exhibits. It’s a great foul weather destination for a half day.
If you’re really into frozen yogurt, Ayelada uses only locally sourced ingredients for all of its house-made flavors and is a short drive from the museum.
North of Pittsfield you’ll approach Hancock, one of the larger ski resorts of the Berkshires, as well as, a concentration of outdoor activities if you are traveling with older children.
Hancock
Hancock Shaker Village is an excellent place to take younger children who enjoy hands-on educational opportunities around farming, milking cows, and caring for animals.
Uncle Don’s Barnyard nearby offers more of a family farm experience with fall and summer activities for younger children (including a large Halloween festival for the month of October). There is a large play structure area to run around in addition to goat feeding and more predictable offerings.
Jiminy Peak in the winter months offers a ski and snowboarding resort, and in the warmer months, a really fun mountain adventure park, alpine slides, and other such things. It’s something we do on every trip to the area for my kids after dragging them through resorted homes and art museums. There are bouncy houses and activities to do, and it works well for children three and older.
Restaurants North of Pittsfield
While it doesn’t look like much, the place to eat in the area on Route 7 is the Old Forge, considered a very solid standby for all the locals in the area as well as smart tourists who hear about it. Everyone loves their wings, and the food is made to order. Expect waits at peak meal times, however.
Williamstown & North Adams
If you’re not visiting this charming town for a reason related to Williams College, it’s really all about the summertime Williamstown Theater Festival or it’s art museums: Williams College of Art and the Clark Art Institute. Both museums have collections worthy of global acclaim, and the Clark boasts an incredible expansion project that was completed in 2014.
Children receive gallery kits with sketch pads and pencils and visual guides to enjoy the collections. For parents used to bribing children with presents from the museum store (guilty!) if they allow parents to enjoy the art, please be warned that every high-design toy at the Clark seem to cost more than $40. You’ve been warned.
Mount Greylock
Given the choice between hiking or driving up Mt. Greylock, I have to say our choice to drive up was a good one. Ascending Massachusetts’s highest mountain, I kept wondering if J.K. Rowling had chosen the Berkshires as the seat of American wizardry education with purpose, or via a quick Google search, to find a tall summit near Harvard and Yale.
She placed Ilvermorny School of Witchcraft and Wizardry at the top of Mt. Greylock, and as we approached the monument at its summit I wondered whether she attended the Williamstown Theatre Festival one summer or visited Mass MoCA? The Berkshires can bewitch anybody.
North Adams
North Adams holds an unrivaled experience for families: Mass MOCA. It takes little effort to engage children at Mass MOCA compared to any other museum. With gallery spaces the size of football fields, the scale of the museum and its work captures the attention of children easily.
The kid center, Kid Space, inside is complimentary to visit and well designed to entertain families before or after gallery visits. Children can choose from a variety of projects to complete inspired by the the permanent and temporary exhibits.
Both its on-site cafeteria and the adjacent sit down restaurant, Gramercy Bistro, offer some of the better meals in town.
Hopefully you have found many reasons to plan a trip to the Berkshires. If you seek additional trip advice, be sure to join Luxe Family Trips, our private Facebook group where the well traveled advise one another or reach out to me for a private one-on-one consultation.
