Curator’s statement
Experience the calm, grounding energy of the Berkshires on your next girls’ trip. A four-season destination where you can be relaxed and indulgent or social and active. There’s an incredible amount of outdoor activities to choose from, including hiking, skiing, horseback riding, and swimming. Arts and culture abound, and the restaurant scene offers a robust amount of farm-to-table options. Lastly, a day at one of the Berkshires exceptional spas is not to be missed!
The Fora Difference
Book with Meri Horn to access exclusive perks and experiences on your trip.
Killer perks
Free upgrades, spa credits and more—we got you
Personalized recs
Customized travel planning for your style
Insider knowledge
Expert advice from people who’ve actually been there
Where to stay
Unlock perks by contacting Meri Horn to book your trip.
Day 1: Arrival, cocktails & dinner in Lenox
Check into your hotel in the afternoon. The Berkshires is only about 2.5 hours from New York City, making it a very manageable drive. Spend a little time enjoying the hotel pool or taking a walk on the grounds before getting ready for dinner in Lenox.
Start your night at dulu inside Doctor Sax House with a creative cocktail before heading to Brava to share some tapas and a bottle of wine. If you’re ready for more drinks after that, Ombra is the perfect lively bar to keep the night going. Then head back to the hotel to get a great night’s sleep!
Day 2: Wellness reset
View from the top of Monument Mountain
Start your day with a hot yoga class at Greenhouse Yoga in Great Barrington. Class ends with a frozen towel, which will leave you feeling refreshed and rejuvenated.
Next, grab a coffee at Ilse Coffee next door and stroll down Railroad Street and Main Street and pop in to the adorable boutiques lining the streets, including Artemesia, Westerlind, and Barrington Outfitters.
When you are ready for lunch, head to Bistro Box. Pro tip: Arrive by 11 to avoid the line. Everything is delicious, but some favorites are the Breakfast Wrap, the Asian Salad, or the Box Burger. Don’t skip the slushie flavor of the week or the strawberry lemonade.
After lunch, if you’re ready for more exercise, head to Monument Mountain for a short but rigorous 3.5 mile hike.
Book an afternoon massage at the hotel before dinner.
For drinks and dinner, head back to Great Barrington and grab a cocktail at Mooncloud or Half Rats before dinner at The Prairie Whale. End the meal with their amazing affogato!
Day 3: Culture, sweet treats & departure
Living Room at the Mount
Sleep in on your last morning or enjoy one last spa treatment before heading to brunch at Starving Artist Cafe in Lee. Super fresh ingredients make their savory crepes an amazing option. Add a matcha latte or a smoothie to drink.
Next, visit the Mount, Edith Wharton’s Gilded Age mansion and estate. Walk the impressive sculpture-filled grounds and tour the house before enjoying a glass of champagne at the Terrace Cafe overlooking the property.
On your way out of town, don’t miss a stop at High Lawn Farm’s creamery for the freshest ice cream you’ve ever had. Pick up some of their artisanal foods and products at the shop as souvenirs.
Need to know
This is an ideal itinerary for warm weather. In the winter, add a ski day at Butternut or Bousquet.
Travel Advisor
Meri Horn
Get in touch with Meri Horn
Did you like this guide? Reach out to customize and book your own experience. Or, just to chat about travel in general.
You can expect a response from Meri Horn within 1–2 business days. You’ll also be subscribed to our traveler newsletter (you can unsubscribe at any time).
For more inspiration and insider recommendations, visit our Massachusetts page.