The Pickering House Inn: Luxury, History and Charm in Wolfeboro, New Hampshire

Article by Nancy Dunmire, Staff Journalist – IPA Magazine Travel

The Pickering House Inn: Luxury, History and Charm in Wolfeboro, New Hampshire

North, South, East, and West—no matter which direction you travel in New Hampshire, you’ll find yourself gliding along winding country roads, surrounded by vast green forests and timeless scenery. Eventually, those roads lead to one of New England’s most charming destinations: Wolfeboro, New Hampshire, proudly known as “The Oldest Summer Resort in America.”

This lakeside town is full of history, beauty, and classic New England character. Grand homes line Lake Winnipesaukee’s shore, quaint shops fill the village center, and the pace of life slows just enough to let you breathe it all in. But tucked just steps from the heart of downtown is a treasure worth a journey all its own: The Pickering House Inn.

A Historic Legacy, Reimagined in Luxury

Originally built in 1813 as a tavern, the Pickering House Inn has lived many lives—boarding house, family residence, even a once-condemned property—before being saved, restored, and reimagined into one of the most extraordinary boutique inns in America.

Built by John Pickering, the tavern and barn were later purchased by Daniel Pickering in 1815 and transformed into his private residence. He also owned a large portion of the surrounding land. In the 1870s, this very barn was transformed by Pickering’s daughter-heir into a three-story housing for railroad workers. 

This incredible, historic property was eventually left to deterioration, and was faced with plans to condemn.

The building was lovingly rescued in 2016 by Peter and Patty Cook, whose vision and artistry brought the house back to life. Preserving original doors, windows, and timbers, they created a balance of old-world charm and modern comfort. By July 2018, the inn reopened to acclaim, and within a year it was listed on the National Register of Historic Places and named the #1 Best Inn in New England—and then in the Nation.

Now, under the care of new owners Doug and Paige Babcock, the story of this historic landmark continues to unfold with warmth, elegance, and hospitality.

Stepping Inside

Crossing the threshold of the Pickering House feels like entering both another era and another world. Ten guest rooms are each exquisitely designed, blending historic architecture with modern indulgences:

-Luxurious bedding that invites the deepest sleep, like drifting onto a cloud.

-Heated showers with digital thermostats, ensuring every detail of comfort.

-Plush robes that wrap you in softness.

-Automatic blinds and curated lighting that create an atmosphere of rest and relaxation.

Every corner tells a story—historic photographs line the walls, antiques mingle with contemporary design, and the house itself whispers its centuries of tales. My personal favorite? ‘The loft suite‘, where light pours in from above, offering a hideaway that feels both cozy and grand.

Each element has been designed not just for beauty, but for joy. From wood floors gleaming with care to the blend of original posts and beams reimagined in the dining room, you’ll sense the devotion behind the restoration at every step.

Gathering Spaces That Feel Like Home

Beyond the rooms, the inn is filled with thoughtfully appointed sitting areas, welcoming nooks, and hallways that invite you to linger. Coffee stations are elegantly arranged for guests, while the dining kitchen resembles a chic café. Here, mornings begin with a gourmet breakfast—freshly cut fruit, warm scones, breads, toppings, and creative entrees—all served with a focus on freshness and detail. Fresh flowers, thoughtfully placed throughout the house, bring a touch of color and life to every space—even in the dining room, where they make each meal feel like a celebration.

Then there is the Barn. Once a real-live housing for working animals, now a breathtaking event space that feels both rustic and refined, it rises with soaring ceilings, balconies above, twinkling lights strung across the beams, and long wooden tables and chairs polished to perfection. It’s an atmosphere that seems almost made for weddings, milestone celebrations, and unforgettable gatherings.

Step outside, and you’ll find a beautifully appointed patio, complete with a modern electric fire table, perfect for cozying up with a glass of wine as the evening air settles over Wolfeboro. It’s yet another space designed for conversation, comfort, and delight.

Doug and Paige, the inn’s gracious new owners, hope to open the Barn to not only destination weddings and private events, but also to local community celebrations and special occasions—a living extension of the inn’s spirit of hospitality. During our time together, there was an aire of excitement over their new acquisition/adventure! They are wonderful hosts, warm and welcoming, and with years of experience in the hospitality industry, Wolfeboro can expect Pickering House Inn to be a substantially significant and iconic gathering place.

The Heart of Wolfeboro

What makes a stay at the Pickering House Inn even more magical is its setting. Step outside, and you’re on the edge of Wolfeboro’s village center, with its lakeside activities, trolley rides, ice cream shops, delightful restaurants, and boutique shopping. In summer, the lake sparkles with boats and swimmers; in winter, the town transforms into a cozy, snow-dusted wonderland. Visit their website Pickeringhousewolfeboro and indulge in timeless beauty; your home away from home.

And with Portland, Maine just an hour away, this hidden gem is closer than you might imagine.

Why You’ll Love It

The Pickering House Inn is more than a place to stay—it’s an experience of history, luxury, and warmth. Whether you’re drawn by its centuries-old legacy, its nationally celebrated design, or simply the comfort of a night spent in unparalleled elegance, this inn is a destination all its own.

Wolfeboro may be the oldest summer resort in America, but the Pickering House Inn has proven that history and modern luxury can dance together beautifully. For those seeking both charm and indulgence, it’s truly unforgettable.