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36 Hour Guide: Lenox, MA

The Berkshires Girls Weekend Guide!

Thinking of taking a trip to the Berkshires? Here is the perfect weekend guide to follow. Lodging for a big group, dinners out, a spa day and a delicious brunch before departure - what more could you ask for? Below is our itinerary for a late October weekend getaway in Lenox, MA.


A three hour drive from NYC, the Berkshires is the perfect place for a relaxing weekend getaway. Choosing to visit the Berkshires in the fall comes with the added bonus of beautiful and brightly colored fall foliage. However a cozy winter weekend could be equally as adorable with silent snowfall and hot chocolate nights.

The House: with 10 girls, we opted to rent a house vs booking hotel rooms. Home Away is a great option for huge Berkshires homes that can comfortably accommodate large groups. If you’re interested in our exact house, it is linked here: https://www.homeaway.com/vacation-rental/p660967vb?adultsCount=10

This house was ideal for our group, mainly due to the large living room. It’s so rare that you get to spend time just sitting on the couch, drinking wine and catching up with all of your college girlfriends. Having such a large communal space really set the tone for a fun and relaxing weekend for us.

Lenox: while there are many small towns that make up the Berkshires, Lenox felt the most on brand for us. We had our home that was nestled away on a quiet tree lined street, surrounded by beautiful foliage, and the best restaurants and spas were only a short drive away.

Spend the early afternoon settling into your weekend home, then head out to a big group lunch to get the party started.

Lunch: Alta Restaurant & Wine Bar: https://altawinebar.com/

Located in downtown Lenox, Alta was the perfect arrival lunch spot for us. While it looks tiny from the outside, there is a back room which can accommodate large groups. Order any of their salads and a glass of sauvignon blanc. The portions are large and the ingredients are fresh.

Post Lunch Cocktails: Olde Heritage Tavern: https://theheritagetavern.com/

After lunch head to The Olde Heritage Tavern for some cocktails. This place is no frills, but definitely fun.


Dinner Night 1: Hotel on North: https://hotelonnorth.com/eat-drink/eat/

A great spot in downtown Pittsfield, MA - about a 15 minute drive from Lenox, MA. This restaurant has big windows, plenty of seating, a great American menu and superior cocktails. On Friday night they also had live music which was an added bonus. Get the shrimp cocktail, deviled eggs and share a bunch of pastas.

Day 2:

Spa Day at the Blantyre: https://blantyre.com/spa/

Book a spa day at the Blantyre. They can accommodate large groups by splitting up your party into 3 afternoon time slots. We recommend getting bottles of champagne so you can drink and catch up in the relaxation room while waiting for your service. Massages and facials were the 2 services of choice for our group and they did not disappoint.


Lunch After the Spa at the Cranwell, Sloane’s Tavern: https://cranwell.lpages.co/dining/

Note, the Cranwell was under construction while we were there, but Sloane’s Tavern, the restaurant on the property was open. Pop in here for a post spa lunch. Get the turkey BLT sandwich and a glass of sauvignon blanc.

Dinner on Saturday Night at the Kemble Inn: http://kembleinn.com/

It doesn’t get more Berkshires than the Kemble Inn. A favorite of RHONY star, Dorinda, the Kemble Inn offers a premium dining experience. Get there about an hour before your reservation, preferable right before sunset to enjoy cocktails by the outdoor fire pit. After cocktails, move into the main dining room for dinner. The menu changes seasonally and the food and service was top notch. After dinner head into the lounge to sip espresso martinis by the fireplace.


Day 3: Departure Day

Head into town for brunch before you hit the road.

Brunch: Haven Cafe: https://havencafebakery.com/

This is an place your order and we will find you a table kind of place. But the crowd moves quick and we had no problem getting a table within minutes, even at prime brunch time with a large group. Get the croissant french toast and a latte.

Overall - I would highly recommend a Berkshires weekend trip, whether it’s with your best girlfriends from college, or a romantic getaway with your significant other. It’s the perfect place to unwind and unplug.

If you have visited the Berkshires and have other favorite restaurants / activities - feel free to leave them in the comments below.



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