The Retro Weekend Getaway That Should Never Go Out of Style

published Jun 9, 2023
We independently select these products—if you buy from one of our links, we may earn a commission. All prices were accurate at the time of publishing.
collage showing a large inn, garden flowers, a rocking chair, and an Inn sign
Credit: Photos: Shutterstock, Getty Images

Let me paint you a picture: You wake up in a four-poster bed covered by a soft patchwork quilt. Antique tchotchkes furnish the room, which is called something like “the lilac room,” and the walls are a soft shade of violet. You pad down the carpeted stairs, which may dip in the middle due to age, and sit down at a table where you scoop generous portions of homemade jam onto a fresh-from-the-oven biscuit. A feeling of cozy contentment settles upon you. No, it’s not heaven. It’s a classic bed and breakfast. 

The #bedandbreakfast hashtag on TikTok has nearly 60 million views. In one of them, there’s a young woman in a montage of wallpapered rooms, ocean views, and tables set with bowls of fruit. The on-screen caption says, “It is what it is (I ran away and became an innkeeper in a small town by the water).” The profile, @innkeepercaroline, depicts lots of moments in her life as an innkeeper, and it’s an easy way of life to dream about. Bed and breakfasts by the water and inns in quaint towns combine all of the cottagecore decor and coastal grandmother charm and package it into the promise of an alternate lifestyle where you could be a regular at the one coffee shop in town and write the next great American novel in all the time spent not looking at your phone. 

Of course, being an innkeeper means real, hard work. But spending the weekend at one? That’s just dreamy. Some of my earliest travel memories are rooted in the small inns and B&Bs I stayed at with my family. Despite the countless hotels that punctuated our cross-country road trips, these independently owned stays just stood out. Yet in my own travels as an adult, I’ve almost exclusively booked hotels and Airbnbs, often choosing the cheapest price or most central location over the accommodation itself. So when I thought about writing this love letter to the old-fashioned inn, I knew I needed to refresh my memory about what makes the experience so special. 

Credit: Red Lion Inn

And I knew just the place to do it: The Red Lion Inn. Situated in the Western Massachusetts town of Stockbridge (population: 1,827), the 250-year-old building is an iconic presence on Main Street. When my boyfriend and I pulled up on the first perfect-weather day of spring (no jacket needed, but not yet sticky with sweat — is there any better feeling?), the first thing I noticed was the broad front porch filled with people sipping drinks and just sitting in rocking chairs looking out contentedly. If the image sounds familiar, that’s likely because you’ve seen it in the 1967 Norman Rockwell painting “Stockbridge Main Street at Christmas.” Save for the snow-capped cars, driving down that street this spring didn’t look very different. 

Credit: Sofia Rivera

Entering the Berkshires inn gave me that same feeling of nostalgia, like walking into a vintage postcard. It’s that sense of history you don’t tend to feel in chain hotels or sparsely furnished Airbnbs. When I met Sarah Eustis, the founder and CEO of Main Street Hospitality, she told me about how she used to spend summers housekeeping at the inn when she was a teenager and her grandparents owned the place. She explained that the fresh daisies she keeps in the entryway and in each room are in honor of her grandmother and told me about the inn’s historian, who used to be Normal Rockwell’s personal secretary. There were bits and pieces of history everywhere I looked. 

Credit: Sofia Rivera

The halls of the Red Lion Inn are full of storied surprises: You’ll find a closet-sized room furnished with a wall-mounted telephone and papered in old covers of The Saturday Evening Post; antique hutches, China cabinets, grandfather clocks, and an ornately carved wooden rocking horse; high shelves lined with porcelain teapots; and long runners padding your every step. It’s a self-contained world, of a different era. Beyond all the antique-filled nooks and crannies, the inn houses not one but two boutiques (Shop Around the Corner, a sunny gift shop that looks like a tea party in store form; and Township Four, a chic boutique filled with plants and homeware, where I’d like to furnish my entire apartment). There is a formal dining room draped in white tablecloths and red carpet and a casual tavern decked out in wide-plank wood floors and suspended lanterns. Through a discreet door and down a flight of stairs, there is a speakeasy-like pub where we sat at the bar and listened to live piano music. 

In a New York Times article from 1982 titled “Bed and Breakfast, the American Way,” the author writes that in speaking with guests and hosts of B&Bs, “Almost all believed that B&Bs provided an antidote to the sterile monotony of chain lodgings. Behind many of their comments lurked the specters of loneliness and boredom — consequences of the shrinking size of the American household and the increased routinization of work in a highly technological society.” Although I’m writing this 41 years later, the sentiment holds. In contrast to the tight elevator smiles of many of my hotel stays, our weekend at the Red Lion Inn felt characterized by warmth and intentionality. No one was bustling down hallways to get where they were going — they had arrived. 

Credit: Sofia Rivera

It’s the sentiment that characterizes inns and B&Bs all over the place, as they’re often situated in smaller towns or slightly away from the buzz of major attractions, and it makes the stay itself so comfortably indulgent. To find a similar getaway near you, try using a site like Bnbfinder, which offers a searchable database of these kinds of properties around the country. You can also post in a neighborhood group for nearby recommendations to find independently owned spots that might not turn up in search results as easily. It can take a little more time than going to your favorite booking site, but it’s time well-spent. 

Thanks to the miracles of modern technology, travel can mean so many things, from staying in a stranger’s spare bedroom halfway around the world to luxuriating in a five-star hotel, and all of those options offer unique experiences. But as you make your summer travel plans, I’m telling you, there’s something special about a weekend at an old-fashioned inn. On our way out, just before we stepped onto the grand front porch to get in the car and drive home to our busier lives, we stopped at the guest book resting on a round table. We read the other parting comments and signed at the bottom of the page that began, “Just as wonderful as everyone said it would be.”