This weekend Will, Rory, and I are hitting the road for a little weekend getaway in the Berkshires. Despite growing up in New England, I’ve spent very little time in the area and I can’t wait to explore! We’ll be staying in Lenox, Massachusetts, so if you have any recommendations on what to see and where to eat in the surrounding towns, I’m all ears!

It’s going to be relatively chilly for our trip so in addition to my winter coat, I’ll be bringing lots of cozy sweaters and the snow boots I’ve been living in all winter (seen here and here). I also just ordered this classic trench coat so I’m hoping it will be warm enough to wear that one afternoon. Can you tell I’m seriously ready for spring?

design darling berkshires packing list

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  1. Blueberry Hill in New Lebanon, NY (close by!) is awesome for breakfast/lunch. Rouge for dinner in West Stockbridge, Alta and Nudel in Lenox, and I second everything everyone already said! Grew up in and moved back to the Berkshires after college, you’ll love it!

  2. Another +1 for Baba Louie’s, it’s to die for! Great Barrington has lots of great shops for clothing, gifts, art, candy!, books, etc. Canyon Ranch Spa/Resort is breathtaking – even if you don’t get spa treatments it’s worth a drive or walk through just to see the grounds.

    I lived in the Berkshires for a few months in the winter of 2010 and really loved it. It’s a great place to disconnect & go off the grid, Rory will love it 🙂 Enjoy!

  3. I went to the Berkshires a few years ago and definitely plan to go back at some point. It’s so peaceful and there are so many interesting things to do.

    My favorite spot was The Mount, Edith Wharton’s estate. The house and grounds are beautiful and the docents are very knowledgeable about Edith, her work and the area. (My favorite spot on the grounds was her pet cemetery!)

  4. I grew up in Great Barrington (the town just south of Lenox)!

    The Mahaiwe Performing Arts Center, an beautifully renovated historic theater in Great Barrington, is showing Casablanca. It is $10 for wine or beer at the café next door and then the movie! (My mother works in their finance department and, inside scoop: they will be giving roses out at the end of the show)

    Baba Louie’s pizza is amazing (although there is usually a long wait so that is something to note!)
    Karen Allen, (actress from Animal House and Indiana Jones) has a wonderful fiber arts shop in Great Barrington. She can often be found working in the shop! I highly recommend stopping in to browse.

    For an incredible mix of vintage and new clothes and home goods, Griffin in Great Barrington is awesome! Sometimes on wintry days, they serve delicious homemade mulled wine!

    The over 25 under 40 crowd in The Berkshires can be found enjoying dinner at Cantina 229 in New Marlborough. It is amazing food in a beautiful location. A bit more hip than Wheatleigh or The Old Inn on the Green.

    For breakfast, I recommend The Southfield Store. The same owners as The Old Inn on the Green. Botanica on Railroad St in Great Barrington and Fuel are both great stops for coffee. The Home Sweet Home Doughnut Shop in Great Barrington is the best place for homemade doughnuts. Let Debbie know that I sent you!

    A trip for another weekend would be to go to Salisbury, CT or Hudson, NY! (Both are an easy drive from Lenox but a bit tight to do on a weekend)

  5. One of my friends has a house in Lennox, but we always head over to Great Barrington for the food and shops – Baba Louie’s pizza is a must!!

  6. You’re going to have the best time! I spent a summer studying voice at Tanglewood, and go back to visit all the time (it helps that one of my best friends parents live right nearby). I echo all the recommendations already made, and would also mention Stockbridge (a short drive away) – that’s where the Norman Rockwell Museum is located. If you’re over there anyway, it might be worth checking out the National Shrine of the Divine Mercy, just because it’s a beautiful chapel in a beautiful location. Make sure to visit The Bookstore (complete with wine bar!) while you’re in Lenox, too! Oh, I miss the Berkshires so!!!

  7. Dalton, MA is so cute! My friend opened a brewery called The Shire, the space is amazing (old paper factory) with live music and full bar if you don’t want beer!

  8. You must stop at the Arcadian Shop in Lenox. In addition to being one of the best shops for outdoor gear, they have a charming little cafe for coffee, soup, sandwiches. it’s called the Trailside Cafe. In addition, it shares a parking lot with Kennedy Park where you can hike or go snow showing (rentals available at the Arcadian Shop). In addition we love Canterbury Farm. Can rent cross country skis, snow shoes and even skates if you would like to skate on their pond. It is filled with beauty and charm. Have always met lovely people at both of these places.

  9. I grew up in the northern part of the Berkshires and would highly recommend heading to either MassMoCA or the Clark Art Institute–great museums for chilly winter days!

  10. Hello!

    I grew up in Lenox! Lots of fun things to do in the area! In Lenox, I would recommend a walk through the grounds of Tanglewood, watching the sunset/sunrise at Olivia’s overlook, catching a show at Shakespeare & Co., and heading into Annie Selke’s new store right in the middle of town. Near Lenox is another small town called Great Barrington, which has a bunch of cute boutique shops to poke into (specifically Church St. Trading Co., Louisa Ellis, and Farm & Home) and delicious restaurants.

    To eat:
    1. Breakfast/Brunch:
    – Haven cafe right in the middle of Lenox
    – Six Depot cafe in West Stockbridge (approx 15 minute drive. You’re halfway there if you spend the morning at Olivia’s overlook)
    2. Dinner:
    – I would highly recommend Baba Louie’s in Great Barrington (hands down the best flatbread pizza I have EVER had)
    – District Kitchen & Bar in Pittsfield, MA
    – The Wheatleigh in Lenox, MA for a very upscale, fancy, delicious 4 course meal

    Hope you enjoy Lenox!

  11. Not sure if Edith Wharton’s home is open (“The Mount”). Definitely eat at The Red Lion Inn! Also, Herman Melville’s home (you can see the room where he wrote “Moby Dick”), also the Norman Rockwell Museum. The Berkshires is a treasure trove of literary delight (Nathanial Hawthorne lived there as well). Enjoy!

  12. We usually go to lenox in the summer to visit Tanglewood – the BSO and Boston Pops are amazing! For restaurants, try Shots Cafe for breakfast and Firefly or Table Six for supper. It’s a pretty sleepy town in the off-season, but I would highly recommend going to The Mount if you’re an Edith Wharton fan (or just want to check out a historic home!). I also really like the local museums – Mass MoCA, the Norman Rockwell Museum, and Ventfort Hall Mansion and Gilded Age Museum. If you’re looking for an easy (and scenic) hike, check out the area at Olivia’s Overlook.

  13. You should visit the Norman Rockwell Museum! We had a great time when I visited with my family! (It even kept my younger brothers interested!)