Will, Rory, and I had the best time in the Berkshires this past weekend! We were invited up to experience Annie Selke’s new inn 33 Main in Lenox, Massachusetts, and both the inn and the surrounding area exceeded my every expectation. While the overcast weather put a slight damper on our visit, it was such a relaxing little getaway and the inn gave me lots of interior design inspiration for our new house. I’m dying to head back to experience the area in full bloom in the spring or to see the foliage in the fall!

33 main lenox ma on design darling

design darling berkshires trip

33 main annie selke

33 main astor room

33 main lenox ma

design darling 33 main


We stayed in the dog-friendly Astor room at 33 Main and the blue and white color palette was right up my alley. We have several Annie Selke pieces in our home (including this striped rug in our living room, this jute rug in our dining room, and a variety of bath towels from her Pine Cone Hill line) and it was such a treat to experience her aesthetic come to life. We were greeted with freshly baked cookies in our room and woke up to gourmet breakfasts prepared by the innkeeper Becca each morning — she even set up a special table so we could eat with Rory at our feet without disturbing the other guests. The decor and the service were both exceptional and the location (in the heart of Lenox, Massachusetts) was a perfect home base for daytime exploring.

design darling the mount

the mount lenox ma

the mount lenox

the mount lenox ma on design darling

design darling winter outfit with moncler peplum jacket

jacket  //  sweater  //  jeans  //  boots

edith wharton the mount

edith wharton the mount lenox ma

j.crew V-neck Boyfriend sweater in everyday cashmere in mediterranean coast

the mount dining room

pale pink dining room at the mount

sorel conquest boots

design darling the mount lenox

My favorite stop of the trip was The Mount, home of author Edith Wharton and a must-see for anyone with an interest in architecture or interior design. Upon arrival we actually learned that the property is dog-friendly (as long as you can carry your pup through the interior) so we immediately drove back to the inn (a quick three-minute drive) to pick up Rory. The three of us walked through the house (let’s be honest, Will carried 30-pound Rory at least 90% of the tour) before retreating outside to let him romp in the snow. I heard from several of you on Instagram that you’ve attended weddings on the property and I truly can’t imagine a more stunning locale — the gardens must be absolutely incredible come springtime.

norman rockwell museum stockbridge ma

design darling norman rockwell

sweater  //  jeans  //  boots

design darling norman rockwell museum

We also visited the Norman Rockwell Museum in nearby Stockbridge, Massachusetts, where the artist spent the last 25 years of his life. We got to see the Four Freedoms in person (posters of which apparently hung in Will’s high school classroom, ha!) and apparently if you visit between April and November you can visit his actual studio on the same property. The museum hosts a massive collection of his Saturday Evening Post covers — there’s an entire room with magazine covers hung floor to ceiling that we easily could have spent hours examining.

no six depot west stockbridge ma

no six depot coffee

design darling berkshires coffee shop no six depot

nutella waffle from no. six depot in west stockbridge mass

red lion inn

polo ralph lauren flag cotton crewneck sweater on design darling

sweater  //  jeans  //  boots

red lion inn on design darling

There are so many other cultural landmarks in the area — MASS MoCA, Shakespeare & Co.Tanglewood — that I’m eager to explore on our next visit. Artistic and literary delights aside, we were absolutely blown away by the restaurants we visited! No. Six Depot was a delicious spot for coffee and lunch (and very Instagrammable if that’s your thing) and an easy pit stop between The Mount and the Norman Rockwell Museum. I’m still drooling over the nutella waffle days later… YUM. We also had drinks at the Red Lion Inn, a historic hotel originally built as a tavern in the 1770s. But the standout from the trip was Brava, an unassuming pizza and tapas spot in downtown Lenox where we took two seats at the bar and ordered bruschetta, Brussels sprouts, and two different kinds of pizza. You guys… I was not expecting to find the best pizza I’ve ever had (no exaggeration) in the Berkshires of all places, but I would literally drive the two and a half hours from Greenwich just to eat here again. I have a goal on my 101 in 1001 list to leave a 100% tip for great service and this was the perfect place to make it happen — the bartender/server was lovely and again, the PIZZA. OMG.

cranwell lenox ma

We also made a quick pit stop at Cranwell where my dad went to high school. It was an all boys’ prep school until 1975 (the year he graduated!) so he and his two brothers were some of the final graduates. It was so fun to see a place he’s talked so much about and to send him a few pictures from the campus, which has since been converted into a golf resort and spa.

dash & albert lenox ma

dash and albert boutique lenox ma

dash and albert store

design darling striped dog bed dash and albert

dash and albert lenox

dash and albert on design darling

Before heading home we took a moment to pop into the Annie Selke boutique across the street from 33 Main to pick up a few souvenirs for our house. Apparently they switch out the inventory in the store every three weeks to feature the newest arrivals and my wishlist just about quadrupled after seeing everything in person. My next Annie Selke acquisition will probably be an area rug for our master bedroom (maybe this or this?) but I have to call out the striped dog bed that so many of you asked about on Instagram over the weekend. The one in our hotel room was the denim/ivory stripe (my photo editing made it look a bit brighter than it really is, sorry!) but we have an old hot pink/white version at home (and if we ever get a second puppy, this color combo is calling my name). We’ve been known to put ours in the back seat of our car to keep Rory comfy (and off our laps) during road trips (or, you know, two cross-country moves) and it works like a charm. 🙂

A big thank you to 33 Main for hosting us this weekend and to all of you for your recommendations on this post — we can’t wait to try more of them on our next visit!


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  1. Fantastic post. Edith Wharton is, in my opinion, the best and most underappreciated American writer, full stop. Ethan Frome, required in so many high schools, is so not representative. I’d recommemd House of Mirth if you haven’t read. Timeless, extraordinary novel about ambition, aging, and class.

  2. I’ve been reading your blog for around 5 years now and this is one of my favorite posts ever. My family used to go to the Red Lion Inn regularly when my late grandfather and grandmother had a home in the Berkshires . Seeing those pictures brought up such a well of memories. My mother had a picture of me “riding” a lion around age 3 framed in our kitchen for many years. I hope you loved your time there; you’ve inspired me to go back.

  3. This is SUCH a pretty hotel! I’m located in Boston and usually go to the Berkshires once every fall, but I’m sensing that I need to have another trip soon and stay there! Looked like a great time. So awesome that they’re dog friendly!

    Mackenzie ||

  4. This seriously looks like the best weekend! That part of MA is so beautiful, and now I’m itching to go check out Lennox (and this property, because anything Annie Selke touches is magic!). Glad Rory seemed to have a great time, too 🙂

  5. I have seen so many people traveling to the Berkshires recently and I haven’t seen any bad experiences. It looks amazing! And I can’t imagine a bad time to go: spring florals, summer to escape the southern heat, fall foliage, and winter snow! Hopefully we can make a trip up soon!

  6. What a great write-up! My husband and I pass this area several times a year as we drive from Boston to Saratoga. I keep saying we need to stop and explore one of these days! We are always looking for dog friendly vacations (and now infant friendly as well).