Weekend getaway from New York · #9 of 10
The Berkshires
Western Massachusetts culture country: MASS MoCA's giant installations, Shakespeare & Company in Lenox, Tanglewood summers, farm-town dining in Great Barrington and green hills to hike between them.
Just three hours from the city, the Berkshires is the ultimate mix of culture and green hills. Think Gilded Age estates in Lenox, MASS MoCA's massive galleries in North Adams, Rockwell's studio in Stockbridge, and Great Barrington's killer dining scene.
Getting there
Hands down the prettiest drive, but it can slow to a crawl when the autumn colors peak.
Your best backup plan if traffic on the Taconic goes south, just keep some toll money handy.
Day 1
Lenox: Gilded Age glamour and lawn picnics at Tanglewood- 19:00 AMDrive
Drive north to Lenox
Beat the crowds and hit the road early. As you leave the city skyline behind, watch the highway melt into three hours of beautiful, rolling Berkshire hills.
📍 New York, United States
Tip · If you're visiting in autumn, seriously, hit the road early. The Taconic gets absolutely packed when the leaves change.
- 212:00 PMFood
Lunch in Lenox village
Welcome to Lenox! Stretch your legs in this picture-perfect village and grab a quick, delicious bite at one of the cozy cafes lining the main drag.
📍 Lenox, Massachusetts
- 31:30 PMSight
The Mount, Edith Wharton's estate
Step right into a novel. Edith Wharton custom-designed this gorgeous 1902 estate and its manicured gardens, putting her own design theories to the test.
📍 The Mount, Lenox
- 43:00 PMSight
Ventfort Hall, a Gilded Age mansion
Get a taste of how the other half lived. This stunning 1893 Jacobean Revival mansion was once a Morgan family retreat and offers a peek into Gilded Age luxury.
📍 Ventfort Hall Mansion, Lenox
- 54:30 PMActivity
Tanglewood grounds
The Boston Symphony Orchestra's summer home is pure magic. Bring a blanket, pack some cheese, and lounge on the lawn for a concert, or just stroll the grounds.
📍 Tanglewood, Lenox
Tip · Lawn tickets for summer shows disappear fast, so lock yours in early if you're heading up between June and August.
- 67:00 PMFood
Dinner in Lenox
Dinner here is all about local love. The restaurants in town source directly from nearby farms, meaning the menus change constantly with the harvest.
📍 Lenox, Massachusetts
- 7NightStay
Check in at a Lenox inn
Rest your head at one of Lenox's charming historic inns or cozy B&Bs. They are super welcoming and put you right next to the estates and Tanglewood.
📍 Lenox, Massachusetts
Day 2
MASS MoCA's massive art, Rockwell's classics, and Great Barrington vibes- 89:00 AMFood
Breakfast before heading north
Fuel up with coffee and pastries in Lenox before taking a quick, scenic drive north to North Adams for a morning of mind-bending art.
📍 Lenox, Massachusetts
- 910:00 AMSight
MASS MoCA
This massive former factory is now a contemporary art playground. Expect giant, room-sized installations inside cavernous brick mill buildings.
📍 MASS MoCA, North Adams
Tip · Don't rush this one. The campus covers several city blocks, so give yourself at least two hours to explore.
- 1012:30 PMFood
Lunch in North Adams or Williamstown
Take a break and grab a bite. Both spots have great local lunch options right near the museum, perfect before you head back south.
📍 North Adams, Massachusetts
- 112:00 PMSight
Norman Rockwell Museum
Check out the ultimate collection of Rockwell's iconic classics, including those Saturday Evening Post covers, set on beautiful riverside grounds.
📍 Norman Rockwell Museum, Stockbridge
- 124:00 PMActivity
Great Barrington's Main Street
This is easily the county's coolest downtown. Wander past independent bookshops, cute galleries, and great cafes right by the Housatonic River.
📍 Main Street, Great Barrington
- 136:00 PMFood
Dinner in Great Barrington
End your weekend on a high note with a stellar meal at one of the town's farm-focused spots before hitting the road home.
📍 Main Street, Great Barrington
- 147:30 PMDrive
Drive back to New York
It's time to head home. Enjoy the final stretch south after a packed weekend of incredible art, historic mansions, and mountain towns.
📍 Great Barrington, Massachusetts
Tip · Sunday traffic heading south can be a headache, so try to head out a bit early to beat the rush.
Where to eat
Expect menus that change with the season, packed with fresh local dairy and produce straight from Berkshire farms.
The absolute epicenter of the region's food scene, offering everything from amazing bakeries to upscale farm-to-table dinners.
Keep an eye out for roadside stands! They're stocked with local cheese, maple syrup, and fresh produce.
When to go
Tanglewood is the main event here. Make sure to lock down your lawn tickets and place to stay way in advance.
The foliage is breathtaking, but it's also prime time. Expect busy roads and inns booked out months ahead.
A total hidden gem. It's quiet and budget-friendly, and indoor spots like MASS MoCA and the Rockwell Museum stay open.
A peaceful shoulder season where the hills turn brilliant green and finding a room is a breeze.
Good to know
- You will definitely need a car for this trip; transit won't get you between these towns.
- Seriously, do not rush MASS MoCA. Give it at least two hours to explore the sprawling mill campus.
- Heads up: if you're visiting in summer, book Tanglewood and your Lenox hotel months in advance.
- Leaf-peeper traffic on the Taconic and Mass Pike is no joke. Leave the city early to save your sanity.
