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Brampton Inn - A cozy fairytale

Story by Annie Hasselgren

Photo by JennQuinn Creative


Hand-raised chickens named after the staff, a cat named Squeaky who is in every wedding, and a cottage that used to be a smokehouse are just a few of the charming details that make the Brampton Inn in Chestertown a picturesque getaway and event venue on the Mid-Shore.


It can be true that “the customer is always right” – and, in some cases, the most informed. When Hilari and Dave Rinehart were regular guests of the Brampton Inn in Chestertown, they had traveled enough to know what they liked and didn’t like about hotels and inns. Upon learning that the historic Brampton was in search of new owners, they knew they could curate something special for future guests.

“We wanted to create a place that felt like home, like you are part of the family,” Hilari Rinehart said. “A place where you can go to unwind and relax.” True to form, the Rineharts embarked on a years-long journey to restore the inn into a getaway and wedding venue that featured all of the natural beauty and local resources that the Eastern Shore has to offer.


With collaboration and sustainability in mind, the Rineharts attended chamber of commerce meetings in Kent County to ensure that they were equipped to do things right. Their focus is on supporting small, local businesses that help to create weddings full of delectable dishes, beautiful surroundings, and enchanting surprises.


“With so much talent here on the Shore, it didn’t make sense for us to work with catering companies in D.C. or Philly,” Hilari said. “We wanted to create an environment where guests can immerse themselves in the environment and connect locally while here.”


Brampton works with vendors such as Chesapeake Chef Services in Kent Island, Wildly Native and Cakes by Abby in Chestertown, Crow Vineyards in Kennedyville, and others. The inn’s wedding coordinator connects couples with local vendors ideal for their taste and style — and the vendors get creative. Recently, Chesapeake Chef Services held a cauldron dinner at the Brampton as part of a special event, delighting guests with their old-world take on dining.



The inn also offers special experiences and packages for their guests at local restaurants, complete with wine pairings at eateries such as The Kitchen at the Imperial in Chestertown. For New Year’s Eve, Brampton staff organized a Chester River boat cruise for guests. Most Friday evenings and during special events, guests are treated to performances by concert pianist Mike Casey, a musician from Kent County who was trained in Europe and returned to his roots on the Shore to share his talents.

Just as the Rineharts pay homage to all the Shore has to offer, so, too, did they jump feet first into a monumental restoration process intended to preserve the deep history of Brampton. The couple bought the inn in the midst of the COVID-19 pandemic, when it was illegal to hold large gatherings. With a 15-person cap, the inn was restricted by event size, but that didn’t stop some couples: the Rineharts hosted a small wedding at Brampton the second week of ownership.

The 5-year, multi-million-dollar plan for the inn was also slowed down by supply chain challenges, but as a history buff committed to ensuring that the Brampton Inn retained its character and presence, Dave Rinehart could be found most days, perched atop a ladder, painstakingly restoring shutters.

"Some of the challenges of maintaining and restoring an historic property is trying to recreate the techniques that were used at the time the building was constructed,” Dave Rinehart said. “For myself, I try to be as true as possible to the spirit of those who built the Brampton, and honor their memory by using the same tools they would have available at the time. Finding the initials of the craftsmen that came before me while doing restoration and being able to match their style and quality of work are some of the greatest rewards, as well as knowing it will be around for future generations."

The Rineharts worked with local masons, builders, landscapers and architects in the restoration and continued to fine-tune the property. Although there is little record of the inn prior to its inception, the Rineharts have learned a great deal of Brampton’s history since 1860. Unlike many large estates that stay within families, Brampton has changed hands — and appearance. The brick part of the house is second generation; previously, there was a wooden mansion that burned down, leaving only one surviving wing. The house was then rebuilt with brick, using uncommon architectural styles for the time period.


The Brampton Inn is a transitional Greek Revival / Italianate-influenced dwelling, an unusual style for the area and the only one of its kind remaining. The 3-story, main section of the house was constructed with a symmetrical five-bay-wide façade and a depth of two bays. Even the use of each structure has also changed significantly. Russell’s Cottage was the smokehouse (complete with hooks where the meat was hung) and the Robin’s Nest Cottage was an on-site vet clinic, with pet-friendly terracotta floors. What is now the Garden Cottage was the horse barn, which was rebuilt and restored with fireplaces at each end.

“The chimneys were for the horses,” Hilari said, laughing. “That tells you how much they cared about their animals.”

Some more recent changes to the property include a 3-tier Renaissance Terrace Garden with a pergola and fire pit, which guests can access via the inn’s veranda or breakfast room, and has become an outdoor oasis that couples love to customize with flowers and other accouterments for their special day.

The Brampton Inn provides a blend of historic nostalgia and Eastern Shore charm with which guests and couples make lasting memories, and the Rineharts plan to hold true to these principles for years to come.

“We love to talk to our guests about what the property was, what it is now, and what it’s meant to guests over the years,” Hilari said. “Couples are coming for weddings and starting their story here, in a place rooted by such a wonderful history.”

Photos by Jumping Rocks Photography

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