Your Perfect Weekend in the Berkshires: Stockbridge, Massachusetts
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Historic cottages with elaborate gardens, world-class museums that will enthrall you for days, and gorgeous mountain vistas that are worth the scramble to get to. Welcome to the Berkshires of Massachusetts!
Not only is this area a haven for creatives – authors, painters, poets, and sculptors, but it also draws in lots of people from away, who come to explore the abundant culture and natural beauty and then find that they never want to leave!
Today we’re exploring the small town of Stockbridge, which is full of natural and historical attractions.
Since a visit to the Berkshires is the best way to explore all four seasons, we’ve created a complete weekend itinerary for all the best things to do in Stockbridge, MA, and beyond.
Table of Contents
Why You Should Drop Everything and Plan a Getaway to the Berkshires
Located in Western Massachusetts, the Berkshire Mountains are actually the southern terminus of Vermont’s Green Mountains, which is a smaller section of the ancient Appalachian Mountains. Are you confused yet?
Hiking trails are abundant in the Berkshires, as are eclectic restaurants, fancy clothing boutiques, antique stores, historic homes, art museums, and lush gardens.
To sum it up, the Berkshires is a collection of beautiful and unique New England villages with cultural offerings normally reserved for big cities. And all of its charms are nestled in one of the most beautiful natural settings you’ll ever lay eyes on.
A visit to the Berkshires is pretty much like visiting paradise, so if you find it difficult to leave at the end of your stay, don’t say I didn’t warn you.
Our weekend itinerary will give you just a small taste of this enchanting area.
And if you want to extend that getaway, say for a week, or even forever, you will find that all of the cities, towns, and villages in the Berkshires have their own secret spots and amazing highlights.
You could explore the Berkshires for the rest of your life and still find unique places that you didn’t know existed!
Insider Tip: We’ve created a free printable version of this 3-day itinerary for Stockbridge, Massachusetts. Download and/or print it to make planning your trip to the Berkshires easy! Sign up for our newsletter, and we’ll send you the printable itinerary straight to your inbox.
Berkshires Weekend Itinerary: Day 1
We’re going to assume that you’re driving to the Berkshires, either from a nearby airport or somewhere else in the Northeast, so our itinerary begins in the afternoon when you get into town.
Get ready for a fun weekend in the Berkshires!
Chesterwood in Stockbridge, MA: Summer Estate of Daniel Chester French
I’ll admit that I didn’t actually know who Daniel Chester French was when I started planning things to do in Stockbridge, but I’m glad that I found out and made the trip to Chesterwood.
Located on 122 acres of woods and meadows, Chesterwood was the summer estate of the esteemed sculptor Daniel Chester French.
French is best known as the sculptor who created the figure of Abraham Lincoln for the Lincoln Memorial in Washington D.C. and the Minute Man in Boston, but his portfolio of amazing works is huge, and he was considered an outstanding architectural and public sculptor during his lifetime and beyond.
French is considered one of the most successful artists of the late 19th and early 20th centuries, producing more than 100 works of public sculpture for the world to enjoy.
Today, Chesterwood is a historic site of the National Trust for Historic Preservation that is open to the public.
You can tour the historic home, the formal gardens, and the woodland trails in the summer and fall, and the grounds can also be toured in the off-season.
Hundreds of French’s preliminary models and final works are on view in the artist’s studio, and the woodland walk is also a must-do, with far-reaching views of the Berkshire hills.
During my visit to the woodland trails behind Chesterwood, I explored the contemporary sculptures of Rick and Laura Brown in an outdoor show entitled One Impulse from a Vernal Wood.
The large-scale art installations were created from felled trees at Chesterwood and harmonized beautifully with the wild surroundings and peaceful landscape.
I suggest setting aside two to three hours to explore the house and grounds at Chesterwood.
Dinner: Cafe Adam in Great Barrington
Time to fuel up with some locally sourced and prepared dishes at Cafe Adam in nearby Great Barrington, which has been impressing guests since 2006. Cafe Adam is located just a few miles south of the Briarcliff Motel, so you’ve got time to pop in and freshen up before heading to dinner.
This is a popular spot for both locals and visitors, so be sure to make reservations in advance.
The seasonal dinner menu includes eclectic specialties that are as unique as they are delicious.
Try the Rhode Island calamari with charred red pepper sauce or the Korean barbecue pork spare ribs. You will be full and happy, I promise. The menu is always changing based on what’s available locally, so if you can’t get my recommendations, don’t be too disappointed.
Berkshires Weekend Itinerary: Day 2
You’ll be spending today exploring the outdoors in the Berkshires — first, another summer “cottage” tour with gorgeous gardens and then a cool sculpture park. Let the fun begin!
Breakfast: Red Lion Inn
The formal dining room at the Red Lion Inn in downtown Stockbridge is a lovely spot to relax and plan your day, but there’s also outdoor seating when the weather cooperates, and the front sitting porch is a great spot to read the paper and watch the world go by.
The breakfast fare at the Red Lion Inn is pretty standard. The pancakes are served with real maple syrup, which I can never resist (true Vermonter!) — can’t go wrong with dessert for breakfast! They also serve more wholesome fare, like yogurt with granola, oatmeal, or poached eggs.
While you’re there, give yourself a little tour of the inn. Every corner and piece of wall real estate is full of antiques and New England art. There’s even a cool teapot collection!
Naumkeag: Formal Gardens Surrounding a 44-Room Cottage in Stockbridge, MA
My favorite stop of the whole trip was my tour of the elaborate gardens at Naumkeag. I toured during the Daffodil and Tulip Festival, which is a popular event, but the gardens are just as lovely in the summer and fall.
Naumkeag is another summer “cottage” in the Berkshires, created for the elite from Boston and New York City to get away to the country for some fresh air. I’m not going to hold it against them because their summer cottages have given us regular folk some beautiful spots to enjoy.
Naumkeag is managed by the Trustees for Reservations and features a lovely gilded-age home and a 48-acre property.
The home was built for Joseph Choate and his family in 1884. Choate was a prominent lawyer in New York City, and the 44-room home was his summer retreat. His daughter, who never married, bequeathed the estate to the Trustees upon her death in 1958.
During her residence, Mabel Choate collaborated with esteemed landscape architect Fletcher Steele to create exquisite formal gardens.
During your visit, be sure to visit the Blue Steps and grove of white birch trees, the Afternoon Garden, Tree Peony Terrace, Rose Garden, the Chinese Garden, and of course, the home, which appears almost exactly as it was left in 1958.
The Daffodil and Tulip Festival features 75,000 spring bulbs on display across eight acres. It’s a spectacle of the natural world!
Lunch: Six Depot Coffee in West Stockbridge, MA
After a delightful morning at Naumkeag in Stockbridge, you’ll be spending the afternoon in the tiny town of West Stockbridge, population 1,300. First stop, Six Depot Coffee, where you can sip a latte or cold brew and indulge in paninis, wraps, soups, salads, or baked goods.
The first time I drove into West Stockbridge, the whole town smelled like roasting coffee.
I parked in the small public parking lot across the street because the parking area in front of Six Depot was already full. Despite the bustle, I was able to order my cold brew and food and find a shady outdoor spot to relax.
The coffee at Six Depot is awesome, and I’m kind of a coffee snob. Sounds like the team at Six Depot feels the same way. They spend a lot of time sourcing their coffee beans and look for coffee that is grown from Arabica trees cultivated at high elevations for delicate, flavorful coffee.
Six Depot coffee beans are purchased from farms or co-ops and are grown using organic and sustainable methods, so you can feel good about every decadent sip.
TurnPark: Outdoor Sculptures Surrounding an Old Marble Quarry in West Stockbridge, MA
Time to work off lunch! Leave your car where it is and walk up Moscow Road a piece to TurnPark, a fun sculpture park and performance space that was created in 2017. I discovered Turn Park by accident and explored the grounds before they opened for the season.
TurnPark is convenient to downtown West Stockbridge and includes 16 acres of outdoor art installations and exhibitions. Paths meander through the woods, along the edge of the quarry, and across a small meadow with art everywhere you look.
The walking paths are gentle and the scenery bucolic, and the larger-than-life sculptures that dot the landscape seem to have been created to interact with and pay homage to the beautiful Berkshire Hills.
Many of the sculptures were created by TurnPark founders, Igor Gomberg and Katya Brezgunova, but many talented artists are represented.
Small seating areas are abundantly tucked in the trees, so be sure to stop and rest while taking in the art that surrounds you.
Norman Rockwell Museum: Discover the Art of Stockbridge’s Most Famous Resident
Did you know that Norman Rockwell is the official state artist of Massachusetts? He enjoyed a long and successful career as an illustrator and spent the last 25 years of his life in Stockbridge.
The Norman Rockwell Museum in Stockbridge features ten galleries of iconic American illustrations, including 998 of Rockwell’s original works, the most significant collection on display anywhere.
Yes, you will find his large-scale, original paintings featuring the quintessential New England scenes that you know and love. But there are also special exhibitions that change with the seasons, as well as educational programs, and a beautiful 36-acre campus.
Norman and Molly Rockwell founded the Norman Rockwell Museum in 1969. It’s considered the most popular year-round cultural attraction in the Berkshires.
Rockwell’s studio, which was moved to the museum property, can be toured between May and October, and there’s a path down to the Housatonic River below.
Read Next: The Best Family-Friendly Museums in the Berkshires
Dinner: Once Upon a Table in Stockbridge, MA
Once Upon a Table is a bistro-style restaurant in downtown Stockbridge, closed Tuesdays and Wednesdays. It’s located down a small alleyway with cozy outdoor seating during the nice weather. It’s a small restaurant, but what it lacks in size, it makes up for in flavor!
While the menu changes frequently, you can be sure to find a nice selection of New England dishes, including pecan-crusted rainbow trout, roasted pork tenderloin, or oven-roasted duck. As I’m not a meat-eater, I went with the grilled veggie ravioli, and was delighted! Save room for dessert, too!
Weekend in the Berkshires: Day 3
Good morning! Today, we’re not wasting any time. Grab a granola bar and pack your daypack for a hike, followed by pastries, and yes, another garden tour.
Morning Hike – Monument Mountain Reserve in Great Barrington, MA
Monument Mountain Reservation is a 503-acre open space reservation located in Great Barrington, Massachusetts.
Once you head into the woods, you can start ascending Monument Mountain, a 1,642-foot summit with far-reaching views. The reserve features several trails, allowing you to create loops of varying lengths.
We hiked clockwise on Mohican Monument Trail, to Peeskawso Peak Trail, to Hickey Trail.
Many people suggest hiking counter-clockwise so you can have a steep ascent and then a gradual ascent, but if you hike clockwise, you can let your dog cool off under the waterfalls in the Hickey Trail before heading back to the parking area or your motel.
The views from Peeskawso Peak are amazing, and we even saw a peregrine falcon from Devil’s Pulpit. The whole hike took just over an hour, perfect for a pre-breakfast workout.
Here’s a cool bit of literary history as documented by the Trustees, who manage the property:
On August 5, 1850, Nathaniel Hawthorne and Herman Melville enjoyed a well-chronicled picnic hike up Monument Mountain. It was their first meeting, and, when a thunderstorm forced them to seek refuge in a cave, their lengthy and vigorous discussion inspired powerful ideas for Melville’s new book, Moby-Dick, which he dedicated to Hawthorne.
Today, more than 20,000 hikers explore these pale boulders, cliffs, and ledges every year.
Hike Monument Mountain: The Details
There is a $6 parking fee at the base of the mountain on Route 7. There are a few picnic tables near the parking area, but no other facilities. Leashed dogs are permitted. Here’s a Monument Mountain trail map that you can download.
Read Next: The Best Day-Hikes in the Berkshires
Late Breakfast: Lost Lamb Patisserie in Stockbridge, MA
While researching my trip to Stockbridge, MA, I came across a story about a young graduate of the Cordon Bleu in Paris who opened a patisserie in downtown Stockbridge.
Owner Claire Raposo opened Lost Lamb Patisserie in 2019 when she was just 19 years old. Today, the patisserie serves classic French pastries with a local flair, as well as locally roasted coffee and specialty drinks.
A visit to Lost Lamb is a huge treat! We got croissants, macarons for our lovely dog sitter, lattes, and a few sandwiches on homemade baguettes to enjoy later in the day.
If I lived in Stockbridge, I would spend each day and most of my money at Lost Lamb Patisserie. I get the feeling that many locals do the same. Hours are Wednesday through Sunday, 9 am-4 pm.
Berkshire Botanical Garden in Stockbridge, MA
If you’re not all garden-ed out by now, your next stop is the Berkshire Botanical Garden, one of the oldest public display gardens in the Northeast.
It was established in 1934 and features dozens of display areas emphasizing plants that thrive in the Northeast. In addition to 24 acres of gardens, be sure to check out the galleries. You can also download an audio tour on your phone to help you navigate and explore.
I loved visiting the rock garden, perennial borders, and the new topiary garden, and the shade trees are gorgeous, too! Give yourself at least an hour to meander the property while planning your own garden.
Lunch: Red Lion Inn in Stockbridge
If you’re a glutton for eating out when you’re on vacation (looking in the mirror), head back to the Red Lion, where you can order a bowl of New England Clam Chowder and an RLI turkey sandwich.
Check out the Red Lion Inn lunch menu here, and eat outdoors if you can.
If a full lunch feels like just too much food, try the next best thing — ice cream! You can score a giant scoop at Stockbridge General Store/ Main Street Cafe — ginger and mocha chocolate chip are clear favorites. Prove me wrong!
I’m sure you’ve looked at your watch by now and realized that your time in the Berkshires is coming to an end, but now that you know how cool Stockbridge and West Stockbridge are, you’ll be planning your next trip to the Berkshires before you even get home.
A weekend in the Berkshires never disappoints, and there are enough things to keep you busy in Stockbridge, MA, for much longer than a weekend!
Berkshires Weekend Getaway to Stockbridge, MA Summary
Here’s a quick at-a-glance summary of our weekend itinerary for Stockbridge, Massachusetts! Bookmark this post so you can come back to it later.
Insider tip: Restaurants book quickly on the weekends, so be sure to make reservations! Many of the attractions require, or at least suggest, buying timed-entry tickets online.
Day One
- Explore Chesterwood in Stockbridge
- Dine at Cafe Adam in Great Barrington
- Check into the Little Lion Inn in Great Barrington
Day Two
- Breakfast at the Red Lion Inn in Stockbridge
- Tour the garden and historic home at Naumkeag in Stockbridge
- Lunch at Six Depot Coffee in West Stockbridge
- Meander around TurnPark in West Stockbridge
- Explore the Norman Rockwell Museum in West Stockbridge
- Dinner at Once Upon a Table in Stockbridge
Day Three
- Hike up Monument Mountain
- Breakfast at Lost Lamb Patisserie
- Explore Berkshire Botanical Garden
- Lunch at the Red Lion Inn
- Ice cream at Stockbridge General Store
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Tara Schatz is a freelance writer and travel blogger with a passion for outdoor adventures. She is the co-author of AMC’s Best Day Hikes in Vermont and currently blogs at Back Road Ramblers and Vermont Explored, where she shares travel tips, adventure destinations, and vacation ideas for the wanderer in everyone.
Love your articles..they so express the flavor of the place you are describing.
The little blue boxes with info for each location are perfectly clear and simple.You make planning a trip easier.
I especially appreciate the “dog friendly” info since my dog and I are headed to the Berkshires for a bit of adventure.
Thanks so much for your feedback, Sharon. It’s very much appreciated!