If you follow me on Instagram, then you saw that Edwin and I snuck away last weekend for a perfect little trip filled with both exploring and relaxing at 33 Main in the Berkshires. Neither Edwin or I had ever been to the Berkshires before. So we loved every minute of the weekend discovering a new place together! Within the Berkshires, we stayed at the little luxury inn, 33 Main, by home furnishings designer Annie Selke. I’ve been a huge fan of Annie Selke for years and featured her on Rhyme & Reason a couple times (as seen here and here) so the minute I saw her bright, beautiful inn open up last year, I knew I had to add it to the top of my travel list!
I love, love hotels and hotel decor and find myself often researching destinations and planning trips to new places around hotels that I hear about or discover on Instagram… this trip was no different (my girlfriend Lauren told me about the inn)! Based on our trip, I’d say that I highly recommend traveling to 33 Main in the Berkshires for a weekend getaway (remember when I first mentioned the Berkshires as a travel destination here?). We went during “off season” in the winter and it was still wonderful. So I can only imagine how beautiful the Berkshires are in the summer and fall. Keep reading for all my top recommendations for the area and to see some snaps of the gorgeous inn.
Cardigan (old – similar, similar) / Long Sleeve Tee / Scarf (similar) / Jeans (also love these and these) / Socks / Boots (more on them here)
Where to Stay in the Berkshires: 33 Main
The first thing we did upon arriving in the Berkshires was check into the inn. Because I love hotel design + decor so much, I was tickled to find out we were the first guests to arrive for the weekend so we got to see every room (you probably saw on my Instagram Story). Annie Selke did such a wonderful job making every room unique and beautiful. It gave me inspiration to open an inn of my own someday, ha!
Two of the rooms are dog friendly so we were so wishing Maybelle had made the trip. Our room was designed in a bright sunshiney floral yellow print. Which made me wake up each morning feeling extra happy. We played gin rummy (our favorite card game) in the living room during cocktail hour. Plus, made friends with the other guests. It was all around too much fun + the inn keeper, Becca, is the nicest person!
Where to Eat in the Berkshires
Edwin and I were so pleasantly surprised by how foodie the Berkshires are! 33 Main is located in the Berkshires town of Lenox, MA so that is where we ate most of our meals. I cannot recommend Brava enough… it was easily our favorite meal and favorite restaurant ambiance! My other dining out musts are Nudel (they change the menu daily based on seasonal selections!) and Alta Wine Bar (amazing for lunch!). We also enjoyed meals at The Olde Heritage Tavern and Bistro Zinc. Otherwise, we had both our breakfasts at 33 Main. Which were our two most favorite meals of the trip (along with Brava!).
Sweater (old – similar, last seen here) / Jeans (also love these and these) / Boots (more on them here)
What to Do + Where to Shop in the Berkshires:
During our stay, I must admit that we did a little shopping. Annie Selke has her own store right across the street from 33 Main, which is so convenient because I found myself being über inspired by the decor in the inn and wanting to shop it myself! I picked up a throw blanket and some gold mirrored stacking trays. I also really liked the store Design Menagerie which was full of home furnishings, clothing, gifts, and more.
Visiting the Norman Rockwell Museum was a huge highlight of the trip (I cried during the tour… it makes you so proud to be an American!). We also had massages at the Cranwell Spa, which were so lovely (it was the only massage Edwin has ever had other than one on our mini moon, ha!). The last activity we wanted to do but couldn’t because it was unseasonably warm was get outfitted at the Arcadian Shop and cross country ski… next time! If we make it back in the summer or fall, we also really want to go hiking. A local told us Olivia’s Outlook is a great option.
The Berkshires is a huge cultural hub for the arts. Other than The Norman Rockwell Museum, The Berkshires offers a trio of amazing art museums that really set the area apart including the Mass Moca, The Clark, and the WCMA. In the summer, The Boston Symphony Orchestra calls the Tanglewood music venue home. The Williamstown Theatre Festival in the summer months brings some of the country’s best actors, directors, designers, and playwrights to the Berkshires. If you love the art of dance, then Jacob’s Pillow is the place for you as they have free dance performances on the weekends in the summer.
Fleece / Hat (also love this hat) / Boots (more on them here)
We had such a fun weekend that I’ve already told my mom and sister that they have to add 33 Main and the Berkshires to their travel wish lists! Edwin and I will be home in Charleston this weekend but is anyone heading anywhere exciting? I’d love to hear about it and maybe add a new destination or two to my travel wish list. xx
Photography by Edwin Eversole. A special thank you to 33 Main for having us.
Everything looks so comfy and cozy, def. a zen spot! 🙂
Completely! I was in such a happy and relaxed state of mind when we were there! It was the most rejuvenating weekend! Definitely add it to your travel wish list. 🙂 xx
This is amazing! I wish you were going there, I could have given some great recommendations…I live in the Berkshires (in Pittsfield) and actually used to work at the Norman Rockwell Museum! I’m so glad you enjoyed your visit!
Meant to say *I wish I knew you were going there*
That’s amazing! We LOVED the museum! It was so well done. Shoots, we would have loved your recommendations but we absolutely loved your neck of the woods either way! So pretty! XO
I’m not too far away in NYC, but I’ve never really considered the Berkshires for a weekend away before! This inn is so darling though that I’m now convinced I have to make the trip!
x Diana // Pearl Girl
Ohhhh you absolutely should! It’s only about a 3 hour drive from NYC so it’s so easy! I can see 33 Main being the absolute perfect escape from the hustle and bustle of the city for a weekend! xx
Everything looks so charming here! Definitely need to add to my hotel bucket list;)
Thanks so much Katie! You’d absolutely love the inn!! xx
So glad you enjoyed yourself in the Berkshires. On your next visit let 1Berkshire help you plan your getaway. We work with journalist all the time in planning familiarization tours, we are the regional tourism council so have lots and lots of incite on fun and unique ways to explore our region.
Thanks so much Lindsey for the scoop! I will definitely reach out the next time we are in the area! We absolutely loved the Berkshires so hope to be back again. 🙂
Looks like such a relaxing trip! I absolutely LOVE this outfit!!! I’m going to have to get it myself ?
It was the most relaxing weekend! You must add the inn to your travel list!! Thank you so much… extra cozy! You’d love it! xx
There is so much more in the Berkshires than Lenox. However, Blantyre Castle is wonderful and in Lenox. My husband and I met there when we both worked there and were also lucky to have wedding reception there. There is also Canyon Ranch and Wheatleigh in Lenox. In north county, you will have to go to the Clark. It is the best museum in the Berkshires and is in Williamstown. Williams College (always #1 Liberal Arts College) is also here and they have a very nice art museum. There is also MassMOCA in nearby NorthAdams. In the summer there is SO much here. Jacob’s Pillow in Becket that has a free gorgeous outdoor stage that is free on Thursday, Friday, and Saturdays nights before the ticketed dance performances, there are also great summer theaters in the Berkshires. Here in Williamstown, is the Williamstown Theater Festival. A couple of years ago Bradley Cooper was in “Elephant Man” here. There are also theaters in Stockbridge, Lenox, and Pittsfield. Of course, Tanglewood that I’m sure you were told about and is the summer home of the Boston Symphony. Beethoven’s Ninth is the best with the Tanglewood Chorus.
Thank you SO much for your wealth of Berkshires knowledge Jennifer! The MassMoca was on our list of things to do but we sadly ran out of time :(. We definitely want to go back in the summer or fall because there is clearly so much to do! your wedding at Blantyre Castle must have been absolutely beautiful! What time of year were you married? Thanks for reading R&R! xx