200-year-old inn’s romantic history repeats itself with new owners

PROCTORSVILLE, Vt. – Built around 1840, the colonial carriage style house on Main Street has over 6,000 square feet of space, a total of 12 bedrooms and 9 baths, a large wraparound porch, and beautiful, original features such as stained-glass windows and detailed woodwork. Narrow staircases behind skinny doors connect the three floors and feel like secret passages.

Tim and Caitlin. Photo by Paula Benson.

Over the many years, the home has been owned by various families, including members of the Singleton family, the same family that owns Singleton’s General Store right across the street. In 1987, the property was known as the Okemo Lantern Lodge when it was purchased by Dorothy “Dody” and Charles “Pete” Buttons, after the couple retired from their jobs in another state and moved to Vermont. The current owners christened the house The Black Bear Den after they purchased the property in September 2022.

There is an idyllic fantasy that has persisted for many years involving moving to Vermont with plans to open a bed and breakfast. From Lifetime movies, to the Bob Newhart Show from the early 1980s, stories of people who leave the “big city” for the romance and challenge of running a small-town inn continue. Few people act on that desire, but some do, including The Black Bear Den’s owners, Tim Brown and Caitlin Dee. They share a similar story with Charles and Dody Buttons, but perhaps one more charmingly impulsive.

Brown and Dee first met at a gathering for a Jeep club they were involved with in Connecticut. 48 days later, they purchased the Proctorsville property. They have been happily hard at work; cleaning, repairing, painting, and restoring the historic house ever since.

Brown retired from what was a regional sales manager job, and now works full time as the property manager for The Black Bear Den, which the couple has been renting out to large groups for short term stays. They may decide to open a B&B at some point, but admit the place needs more renovations before that can happen, and since Dee is still employed as a college professor, she can’t commit to running a bed and breakfast full time just yet.

Right now, Brown says, “Our hopes are to return the inn back to its original condition and create a well-cared for, beautiful home with gardens and more.” Brown admits, the couple has been taking on the work themselves, and “there have been a lot of necessary repairs and upgrades, and it’s been a ton of work already.”

Brown has even extended the restoration project to the timeworn cemetery on the hill above the house, another example of the couple’s commitment to honor the legacy of the property and town. Because the road leading to the cemetery has been blocked off, Brown explained, “No one is tending to it. The whole cemetery has fallen into disrepair.”

Called Proctor Cemetery after the Proctor family who donated the land, the earliest documented burial is from 1816. Buried there are five known U.S. Veterans, of the Revolutionary War, Civil War, the War of 1812, and the Spanish American War.

“Tim made a little path,” Dee related. “He’s been going up there, clearing out dead brush.”

“I’d like to get to the point where it looks nice, with flowers, and grass,” said Brown.

Much like their home, the pair exudes a positive energy. Dee and Brown really seem to be enjoying their adventure so far, laughing as they shared their story with me.

Dee went on to say that after an offer on a different property fell through, she saw the online post with the inn for sale. “It just really seemed meant to be. We didn’t plan to buy something this big, or own an inn, but here we are, and we’re just going with it for now.”

Both Dee and Brown look forward to spending time at the house together, and with their blended family, (they each have two children) and will continue renting to other families and groups who want to visit the area and stay in a unique home.

Someday, they said, they’ll have their wedding at the house.

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