Lanesborough, Massachusetts: The Berkshires Town That Is Very Much Not Mount Greylock

If you've ever driven north on Route 7 out of Pittsfield, congratulations: you've been to Lanesborough, Massachusetts. You just didn't know it, because nothing announced it, and also because you were looking at the mountain. That is the town's whole deal, and honestly, the town has made peace with it.

Let's take a loving, slightly mean tour of the "Gateway to Greylock."

A Brief History of Lanesborough (Or: Why It Used to Be Called New Framingham)

Lanesborough has an origin story with more identity crises than a college sophomore. One of the first Berkshire communities to be settled, it was originally known as "New Framingham." It was first settled in 1753 and officially incorporated on January 21, 1765.

The name we ended up with is a mystery wrapped in a rumor. Tradition has it that a Mr. Lane of England promised the community a bell if they would take his name, but the bell was never produced. So the town is named after a guy who ghosted it on a bell. Other theories include Viscount Lanesborough, a friend of Governor Francis Bernard, who incorporated the town. Whichever origin you pick, someone got a name out of it and Lanesborough got a lanyard.

The town's most famous son is humorist and lecturer Henry Wheeler Shaw (b. 1818), who wrote under the name Josh Billings and gained fame in the 1800s as a sort of Will Rogers observer of the human condition. His "Allminax" obtained a wide circulation. He wrote in deliberately mangled spelling, which means Lanesborough produced the original "u up?" energy about 150 years early. He died in 1885, and the town has been politely waiting for a sequel ever since.

"Gateway to Greylock": Geography for People Who Like Being Somewhere Else

The town's official slogan is "Gateway to Greylock, and the Best of the Berkshires." A gateway is, by definition, the thing you walk through to get to the good part. Lanesborough has bravely branded itself as the lobby.

To be fair, the lobby is gorgeous. At 3,491 feet in elevation, Mount Greylock is the highest point in Massachusetts. Portions of it are in the town, though the summit itself sits over in Adams, so Lanesborough gets the approach, the trailheads, and the humility.

Geography-wise, the town is hard to pin down. Its streets merge seamlessly with Pittsfield's at the southern border, so you may cross the line mid-errand without noticing. The town covers 29.6 square miles, and the population was 3,038 at the 2020 census, which is plenty of room to not run into your neighbors at the transfer station.

There is real outdoorsy goodness here. Pontoosuc Lake is a lake in Lanesborough and Pittsfield, offering public access, and the Lanesborough Town Beach is a very small beach on the north side of the lake. The "very small" is the town's own marketing, and it is refreshingly honest. There's also the Ashuwillticook Rail Trail, which is a mouthful and a lovely bike ride.

Town Meeting Is the Nightlife: Government, Gossip, and Free Pizza

Lanesborough runs on an open town meeting, the purest form of democracy and the slowest form of entertainment. This year's installment was a thriller. It took nearly three hours, but the voters dispensed with the town's business. The Berkshire Eagle noted that one factor might have been free pizza and child care provided in a separate room. Civic engagement, brought to you by pepperoni.

The agenda had real drama. Voters approved a budget for fiscal year 2027, and they argued over a fire truck, plus a dump truck. Somewhere, a culvert sat quietly, waiting for its turn. It's also a year of big changes for the Select Board, which is the town's version of a blockbuster cast expansion.

The demographics tell you who's in the room. The median age skews well above the Massachusetts figure. Owner-occupied housing runs high, so nearly everyone has a stake in the dump truck.

Wikivoyage's summary of the after-dark scene is blunt. There are plenty of places to sleep and eat, but no nightlife to speak of. Your evening options are Lanesborough Day (a community celebration for all ages, with an Elvis tribute artist closing out the live music) or driving to Pittsfield.

Eating, Shopping, and the Berkshire Mall Situation

Food in Lanesborough is comfort-forward and unpretentious. The roast crowd will point out that the dining scene includes Bob's Country Kitchen, Krispy Kone, a pizza house, and a pub that's proud of its wings. Locals will point out that Krispy Kone is a Lanesborough Day fixture, which is more community spirit than most Michelin-starred restaurants can claim.

Then there's the Berkshire Mall, the town's best-known commercial landmark, on the Pittsfield line. Retail has had a rough few decades, and the mall has the energy of a prom decoration left up in October. Residents mostly commute elsewhere for work, which is why the town keeps leaning on tourism, apple orchards like Lakeview Orchards, and the endless supply of hikers who need gas on the way up the mountain.

If you do come, here's a field guide:

• Hike Mount Greylock and take a photo at the summit (in Adams, but we won't tell).
• Bike the Ashuwillticook Rail Trail to feel athletic without committing.
• Swim at the Town Beach, but check the notices first, since the town posts public health advisories for Pontoosuc Lake when the water gets moody.
• Stop for ice cream at Krispy Kone and pretend this was the plan.
• Attend town meeting if you want to see democracy at its most gloriously caffeinated.

The Verdict

Lanesborough is a quiet, pretty, slightly overlooked town with a great mountain, a decent lake, a historic humorist, and a municipal government that will absolutely debate your dump truck for three hours. It's not trying to be the main event, and that's the charm. It's the friend who always drives you to the airport.

Think we were too nice? See the full roast of Lanesborough on RoastMyTown.com.