Back in 2019, I had the loveliest stay in the Berkshires at 33 Main in Lenox, Massachusetts. It was one of those trips that stayed with me long after I returned home. I loved it so much that I booked another visit for my birthday the following year—but then COVID hit, the borders closed, and the trip never happened.
For years, I hoped I’d get back. This year, I finally did—and this time I had a very special travel companion: my dog, Chloe.
One of the things I remembered most from my first visit was an adorable little dog staying at 33 Main. I also remembered how incredibly pet-friendly Lenox was, and I couldn’t wait to experience it again with Chloe by my side.
So, I installed a dog car seat, packed Chloe’s favourite blanket and treats, and we hit the road.
Here’s a quick overivew of our trip!
The Road Trip
The drive from Whitby to Lenox is about six and a half hours, making it one of the easiest cross-border road trips I’ve taken. Once you’re on the highway, it’s really just a few major routes before arriving in the Berkshires.
Travelling with a dog couldn’t have been easier. We found plenty of convenient stops just off the highway, and many of the service centres either welcomed Chloe inside or had small fenced dog runs where she could stretch her legs before we continued on our way.
As usual, Chloe was the perfect passenger. She slept through most of the drive, occasionally waking up to look out the window before curling back up while I listened to far too many true crime and reality TV podcasts.
Before we knew it, we’d arrived in the beautiful Berkshires.
Checking Into 33 Main
Approaching Lenox is part of the experience. The winding roads, mountain views, and charming New England scenery make for a beautiful welcome before you arrive at 33 Main.
Parking is easy, and before your arrival you’re asked to choose a personal four-digit entry code, making check-in seamless if you arrive after staff hours.
Luckily, I arrived while the staff were still there and was greeted with the same warm hospitality I remembered from my first visit.
Chloe and I were staying in the Hollingsworth Suite, one of two dog-friendly rooms at the inn. It was every bit as beautiful as I remembered.
Since my last visit, Annie Selke had refreshed many of the interiors. While the design had evolved, it still reflected her signature style—bright, colourful, elegant, and incredibly welcoming. Every room feels thoughtfully curated without sacrificing comfort.
One of my favourite things about staying here is that you’re truly surrounded by Annie Selke’s designs. The furniture, bedding, rugs, artwork, robes, towels, table linens—even the soaps and lotions—are all part of her collection. If you fall in love with something in your room, chances are you can take one home yourself.
Waiting for us were freshly baked cookies for me and a special dog treat for Chloe—a thoughtful little touch that immediately made us both feel welcome.
Breakfast Worth Driving For
Each evening you’re asked to choose your breakfast time and whether you’d like to dine in the beautiful dining room or outside on the veranda.
If there’s one thing I remembered from my 2019 visit, it was breakfast.
More specifically…
The bacon.
I know it sounds ridiculous to rave about bacon years later, but I honestly wasn’t sure it could possibly live up to the memory I’d built in my head.
It absolutely did.
Perfectly crisp, perfectly cooked, and somehow even better than I remembered. Combined with the beautifully prepared breakfasts each morning, it’s one of the highlights of staying at 33 Main.
Evening Charcuterie Hour
Every afternoon at 5 p.m., guests are invited to enjoy complimentary charcuterie and cocktails.
A fully stocked bar is available for guests to help themselves, while an assortment of cheeses, meats, crackers, fruit, and accompaniments are beautifully presented.
The first evening, I enjoyed a lovely glass of rosé with an individually prepared charcuterie plate. The following night, I poured myself a crisp white wine and sampled from the shared board while chatting with other guests.
It’s one of those thoughtful touches that transforms a stay from wonderful to truly memorable.
Throughout the day, guests can also help themselves to coffee, tea, cold drinks from the guest refrigerator, fresh ice water, and—my personal favourite—those delicious homemade cookies that always seem to be waiting in the kitchen.
Exploring Lenox
One of the best things about staying at 33 Main is its location.
The inn sits right in the heart of Lenox, making it easy to explore everything on foot. Boutique shops, cafés, bookstores, galleries, and restaurants are all just a few steps away.
Even better, many businesses welcome dogs, so Chloe was able to join me while I wandered through town and stopped for coffee.
Lenox has a wonderfully relaxed pace. It’s the kind of place where you naturally slow down, linger over breakfast, browse independent bookstores, or simply sit on a bench along Main Street watching the world go by.
Just outside the village is Tanglewood, the summer home of the Boston Symphony Orchestra, where visitors gather for world-class performances in one of the most beautiful outdoor concert venues in the country.
Surrounded by the rolling hills of the Berkshires, Lenox is also an ideal base for hiking, scenic drives, and exploring charming nearby towns. No matter the season, there’s always something beautiful waiting around the next corner.
A Visit to the Norman Rockwell Museum
One of my favourite outings was visiting the Norman Rockwell Museum in nearby Stockbridge.
Even before stepping inside, the museum grounds are worth exploring. Rolling lawns, mature trees, colourful gardens, and sweeping views of the Berkshire Hills create a peaceful setting that feels like a Norman Rockwell painting come to life.
Walking the paths is wonderfully relaxing. Benches are tucked throughout the property, inviting visitors to stop and admire the scenery.
Already Planning My Return
Some places are wonderful because they’re beautiful. Others are memorable because of the people.
33 Main manages to be both! It’s just such a wonderful play to relax and unwind. It manages to be luxurious and easy all at the same time.
From the beautifully designed rooms and unforgettable breakfasts to the welcoming staff, thoughtful amenities, and pet-friendly atmosphere, every detail makes you feel genuinely cared for.
Returning after so many years reminded me exactly why I’d never forgotten this place.
This trip was everything I’d hoped it would be—and sharing it with Chloe made it even more special.
As we drove home, I was already thinking about when we might come back. Some destinations are worth visiting once.
The Berkshires—and especially 33 Main—are the kind of places you’ll find yourself returning to again and again.
Items in this post may have been provided to me for review, but all opinions are fabulously my own.
