the ceiling
Brandi Lightsey spent thirty years in banking. Born and raised in Colorado, married to a man born and raised in Colorado, living in the mountains at ten thousand feet. She had never lived anywhere else and by every outward measure she never needed to. Then she hit the ceiling. Thirty years in, there was nowhere left to climb and the work had stopped being meaningful.
Her mother died young, a fact that resonated with Brandi, so she decided to take the leap and not live with any regrets.
a listing and a plane ticket
The bed and breakfast was not her dream first. It belonged to her husband Darrel, and to their daughter Billie, who had briefly wanted to be an innkeeper herself before deciding it was not for her. Billie kept scouting listings anyway, and turned up a 230 year old farmhouse for sale in a Massachusetts town none of them had ever visited. The Lightseys got on a plane to see it. Brandi walked into the Harbour House Inn Bed & Breakfast, a 1793 farmhouse built the same year Cheshire was incorporated, and fell in love with the place on the spot.
She quit the bank. They left Colorado, the only home either of them had ever known, and moved east at the tail end of the pandemic.
the closed inn
Here is the part that sounds like bad luck and turned out to be the opposite. They arrived while the Inn was closed. Covid had shut the doors, and for new innkeepers with only a few guests on the books, that dead time became an opportunity.
They gutted and rebuilt. A full kitchen remodel. Every room and bathroom refreshed, new paint, new toilets, new vanities. Last year a new deck. The long neglected yard has been brought back to life too. By the time the world reopened, the Harbour House had quietly become a different inn bearing the same name, a name they kept for the practical reason that reservations already existed for the coming year.
one returning guest
The house has been an inn since the 1990s and the Lightseys are its fifth owners. What they inherited was mostly the building itself. The previous era had left them almost no returning guests. When they took over, one client returned each year. Since then they have created a warm environment and fostered a loyal base of guests who come back year after year.
And they built it deliberately. A new website. New listings. Travel auctions in New York. Brandi describes putting real work into marketing, the kind of unglamorous, persistent effort that does not show up in the photos but does show up in the calendar. Today the Inn draws repeat guests from New York, Boston, Connecticut, Rhode Island, Pennsylvania and Tennessee, and from overseas.
colorado in the house
Their Colorado roots are evident in the Inn. One room is dedicated to Colorado, anchored by a log bed her son built for her, a piece she loves sharing with the guests who stay in that room, surrounded by family art and photographs.
Being from big mountain country shaped the business as well. Where a typical Berkshires bed and breakfast might wind down for the winter, the Lightseys keep the lights on year round and look forward to building a year round client base. May through October is the busy season, with Darrel still running his drywall business on the side.
The Inn is open for all kinds of events. There have not been weddings yet, but the two and a half acres of outdoor space host bridal showers, book club dinners and Lions Club gatherings. The Inn is located in Cheshire, MA, which is centrally located to everything that makes Berkshire County special. It is also conveniently located less than a mile north of the Appalachian Trail.
the undersold berkshires
Ask Brandi about the region and she lights up. The hiking, the biking, the canoeing, the waterfalls. MASS MoCA, the Clark, the Norman Rockwell Museum, Tanglewood. To someone who found the Inn via an online listing, discovering the Berkshires has been a treasured adventure for Brandi and Darrel.
In Brandi's opinion Massachusetts undersells the region, and the promotion that does exist focuses specifically on the Boston Symphony Orchestra and Tanglewood while the wider landscape of cultural and outdoor activities remains unknown and undiscovered by many travelers who would love it most.
It is a striking thing to hear from her, because she is the proof of her own argument. Nobody marketed the Berkshires to Brandi Lightsey. She found it in an inn listing, walked in cold and rebuilt her whole life around it. Her bet is that plenty of other people would do some version of the same, if anyone told them it was here.
go and stay
Until then she does what she has done since the day she left the bank, keeps the lights on, gets creative and continues to build the business with her husband's help.
The work to market, redevelop and improve the Inn has been an ongoing labor of love. But the Lightseys will tell you they feel incredibly blessed, for their neighbors, for the friends they have made here, and for the way this corner of Massachusetts took them in.
Come experience it for yourself. A 1793 farmhouse the same age as the town around it, rebuilt room by room by two people who gave up an entire life to do so, on two and a half acres a short walk from the Appalachian Trail. Brandi and Darrel look forward to welcoming you to the Harbour House.
