Located in the mountains of western Massachusetts, The Berkshires are known best for their outdoor activities and the quaint little towns that make up the region. Though the area is small, there’s no shortage of things to do and see here. From cultural museums like the Hancock Shaker Village to outdoor sites like The Berkshire Botanical Garden, I’ve rounded up a guide on How to Spend a Weekend in the Berkshires.
Where to Stay in The Berkshires
Cost: ~275 per night
Location: Lenox, MA
A quaint bed and breakfast in the town of Lenox, Gateways was our homebase during our weekend in the Berkshires. It’s conveniently located right in the town of Lenox so it’s within walking distance to the area’s best restaurants. I can’t tell you enough how cozy this place was; the bed was a dream which is not something I typically say about a hotel bed. Suffice it to say, this is the ideal place to stay for a weekend in the Berkshires.
Other Hotels in the Berkshires:
What to Do & See in The Berkshires
The Norman Rockwell Museum – Norman Rockwell was an American painter and illustrator best known for the cover illustrations he created for The Saturday Evening Post, an American magazine. This museum in Stockbridge is home to the world’s largest collection of original Rockwell art.
The Mount, Edith Wharton’s Home – Edith Wharton was an American novelist and short story writer who wrote notable works like The Age of Innocence and Ethan Frome. The Mount is designed by Wharton herself who used it as her country home. Today, you can roam through the house and gardens, both with classical Italian and French influences. It’s such a beautiful property, you can easily spend hours here.
Hancock Shaker Village – A former Shaker commune in Pittsfield, this living history museum gives you a glimpse of how the religious group, the Shakers, spent their lives.
Chesterwood Museum – The home, studio and gardens of America’s foremost public sculptor, Daniel Chester French, who designed notable sculptures like the Lincoln Memorial in Washington D.C. I cannot say enough good things about our experience here; the staff is so informative and the studio itself is beautiful. How they managed to craft those large structures in these small buildings is truly an impressive feat.
Naumkeag – Known as the former estate of noted New York City lawyer, Joseph Hodges Choate and Caroline Dutcher Sterling Choate, the Naumkeag property features Gilded Age architecture and stunning, picturesque gardens.
Explore the Towns – The Berkshires are full of small, quaint towns that really epitomize the phrase ‘easy New England living’. A few of my favorites include:
- Great Barrington – One of the larger towns in the area, Great Barrington has a strip of local shops and restaurants like the Prairie Whale and Rubiner’s Cheesemongers.
- Lenox – A small town spanning just a few blocks, you won’t find much to explore here but it is home to some great restaurants so it’s worth popping by for a meal.
- Stockbridge – The setting for Norman Rockwell’s famous Christmas painting, Stockbridge is truly a tiny picturesque town.
The Berkshire Botanical Garden – Located in Stockbridge, the Berkshire Botanical Garden is a great place to spend an afternoon. Walk through their beautiful grounds containing over 3,000 species and varieties of florals.
Olivia’s Overlook – A beautiful lookout spot in West Stockbridge. Bring along a blanket and set yourself up for an afternoon picnic or hike some of the trails nearby.
Mount Greylock – The highest point in Massachusetts, this is the ideal place to take in the area’s views, especially in the fall.
Where to Eat in The Berkshires
The Prairie Whale – A restaurant in Great Barrington, The Prairie Whale’s chef serves up delicious, seasonal fare. Grab a table outside in the summer, order a cocktail and a plate of pasta (depending on the menu’s seasonal offerings) and enjoy the ambiance.
Rubiner’s Cheesemonger’s – If cheese is your thing, Rubiner’s in Great Barrington is a must while you’re in the Berkshires. I recommend popping by their shop to grab some bread and cheese and heading out for a picnic.
Alta – A wine bar and restaurant in Lenox offering dishes made of local and organic ingredients.
No. Six Depot Roastery & Cafe – A local cafe in West Stockbridge serving coffee, sandwiches and pastries.
Pizzeria Boema – A tasty, Instagram-worthy restaurant in Lenox. Pizzeria Boema’s backyard is a great place to grab a cocktail and an appetizer on a summer afternoon.
High Lawn Farm – A family-owned dairy farm in Lee. Stop by for an ice cream cone or stock up on their local goods before heading out of town.
Do you have other recommendations for a weekend in the Berkshires? Leave them in the comments below!1