Welcome to Lenox, Massachusetts: The Town That Misspelled Its Own Name While Kissing Rich People's Feet
Ever visit a place so desperate to impress you that it accidentally reveals all its insecurities? Meet Lenox, Massachusetts – the town that literally couldn't spell "Lennox" correctly when they were trying to brown-nose British royalty back in 1767. It was supposed to be named Lennox, but a clerk misspelled it as Lenox, creating what is arguably Massachusetts' most expensive typo. Originally called Yokuntown, it was set off from Richmond in 1767 and was probably named for Charles Lennox, 3rd duke of Richmond and a defender of colonial rights. Nothing says "we desperately want to be taken seriously" like butchering the name of the aristocrat you're trying to honor.
The Summer Invasion: When Millionaires Descend Like Locusts
The population was 5,095 at the 2020 census, but don't let that fool you. Come summer, this sleepy Berkshire County town transforms into what can only be described as a colonial-era theme park for wealthy urbanites seeking "authentic" cultural experiences. Tanglewood has become famous as one of the world's leading music festivals, attracting more than 300,000 listeners each summer. That's right – this tiny town's population swells by roughly 6,000% when the 2024 Tanglewood season will feature more than 100 performances, including eleven weeks of concerts and other events by the Boston Symphony Orchestra.
Picture this: For most of the year, Lenox is a charming but sleepy village where many locals will tell you that the best time of the year is really the fall. Then summer arrives, and suddenly downtown becomes a parade of Range Rovers and people who think owning a Patagonia vest makes them outdoorsy. Lenox is the site of Shakespeare & Company and Tanglewood, summer home of the Boston Symphony Orchestra, which means locals spend their summers serving $18 artisanal grilled cheese sandwiches to tourists who describe themselves as "cultured" because they own season tickets.
The town's relationship with wealth is... complicated. The school's athletic teams are called the "Millionaires", in acknowledgement of the town's history, though the irony is that most actual Lenox residents are decidedly not millionaires. They're the people who work at the hotels, restaurants, and cultural venues that cater to people who are. It's like naming your high school team the "Ivy Leaguers" when most kids are headed to community college.
The Golden Age: When Rich People Built Vacation Homes and Called Them "Cottages"
Lenox's claim to fame rests largely on what historians call the "Berkshire Cottage era" – the period from 1880 to 1920 when wealthy families from Boston and New York decided the Berkshires reminded them of Switzerland, but with better servants. Lenox became a fancy summer resort, much like Newport, Rhode Island. Wealthy families built huge houses for fun and parties during the summer.
The price of real estate during this era was absolutely bonkers. In 1903, an acre of land in Lenox cost $20,000, which was a lot more than in nearby towns – that's over $700,000 in today's money for a single acre. Imagine paying Manhattan penthouse prices for land in rural Massachusetts because some robber barons thought the views were pretty.
These "cottages" were mansions so massive they made today's McMansions look like garden sheds. The crown jewel was The Mount, a country house that was designed and considered the first real home of the noted American author Edith Wharton. Built in 1902, where Wharton could write about the artificiality of high society while literally living in a monument to it. In its collection is an apology note from Edith Wharton for returning a book late – because even Pulitzer Prize winners had to deal with library fines.
But all good things (and absurdly expensive real estate bubbles) must come to an end. After 1913, it became harder to build and keep up these big mansions. Many estates were sold or torn down after the Great Depression and World War II. Some became schools, others yoga centers, because nothing says "inner peace" like doing downward dog in a former robber baron's ballroom.
Modern Lenox: Still Serving the Rich, Just With Better Marketing
Today's Lenox has learned to package its servitude more elegantly. Our award-winning lodgings offer an unparalleled world-class range of choices, from family-friendly motels to exclusive spas and resorts properties, the town's tourism board crows. Translation: "We have everything from places where normal people can afford to stay one night to places where hedge fund managers drop your annual salary on a weekend spa retreat."
The town is also home to the Pleasant Valley Wildlife Sanctuary south of Yokun Seat, the Wyndhyrst Resort and Golf Club, and a Miraval Spa. Because nothing says "connection with nature" like a $500-a-night wellness retreat where you pay extra to eat locally-sourced kale.
The town does have legitimate cultural attractions. The property was announced as a National Historic Landmark in 1971 and welcomes annually 50,000 visitors who tour the property and learn about Edith Wharton. But let's be honest – half the visitors are there because their guidebook told them it was "refined," and the other half are literature majors trying to get Instagram content that makes them look intellectual.
The Verdict: Charming, But Know Your Place
Don't get me wrong – Lenox is genuinely beautiful. Lenox is spectacular in the fall, when the autumn foliage creates postcard-perfect scenes that would make a Vermont tourism board weep with jealousy. Unlike many seasonal New England towns, Lenox does not shut down in winter but thrives, maintaining a year-round charm that's actually quite impressive.
The median household income sits at $51,750 while estimated median house or condo value in 2024: $437,999, which tells you everything you need to know about housing affordability for locals. It's a town where the people who make it run can barely afford to live there – a very New England problem indeed.
But here's the thing: Lenox has embraced its role as Massachusetts' most expensive summer camp for adults, and honestly? Good for them. They've turned their geographic accident of beauty and their historical accident of attracting wealthy tourists into a sustainable economy. Sure, it's built on serving people who think spending $200 on dinner makes them sophisticated, but at least they're good at it.
So visit Lenox. Enjoy the music, tour the mansions, buy the overpriced cheese. Just remember that you're participating in a tradition that's been going on for over a century: rich people coming to the Berkshires to feel cultured while local folks smile and count their tips.
Think we were too nice to this aristocratic wannabe? See the full roast treatment at RoastMyTown.com, where no town's pretensions are safe.