Southern Charm Beckons in Tallahassee

Historic Inn Attracts a Host of Varied Guests

In March of 2015, one of Tallahassee’s oldest homes reopened its doors as the Park Avenue Inn. An elegant antebellum mansion, it offers guests the opportunity to experience unparalleled Southern elegance. Brilliantly illuminated, chic and spacious, you never would guess that the building is nearly 175 years old.

Lawrence Davidson

The grand, pillared porch of the 175-year-old Park Avenue Inn is rich in history and Tallahassee lore. 


Located in Tallahassee’s Historic District, the home has seen its fair share of owners over the years. Kate Bruner runs the inn’s day-to-day operations and says it’s the history, more than anything else, that attracts guests to Park Avenue Inn.

“The historic background provides a point of interest, as it does for most B&Bs housed in period homes,” Bruner said. “History and hospitality are the draws for guests at a B&B. It’s a far different experience than a chain hotel room.” 

Amanda Hunter

The five rooms, two of which are suites, are well-suited for guests seeking a tranquil space reflective of days gone by. 


Built between 1837 and 1839, the home was constructed and owned by Capt. R.A. Shine for almost five years before Florida achieved statehood. The Second Seminole War was taking place at the time, and it was not uncommon to witness Indian attacks on white settlers, even in Tallahassee. In 1842, the war ended, and the home had survived unscathed. Shine owned the home for an additional five years before later selling it to a chance buyer. 

As the legendary story goes, F.H. Flagg and Dick Wilson had just left a friend’s home where they had been playing poker. On the way home, under the starry sky, they passed the beautiful home and noticed it was for sale. Flagg fumbled with a lottery ticket in his pocket which was, if he won, good for the exact asking price of the home. He declared if he won the lottery, he would purchase the place. The next day Flagg ended up winning and made good on his word. The home was now his. 


In 1884, Flagg passed away and the home was sold to a woman, Hattie Dickenson, who owned it for 10 years before it was acquired by Jane and Simeon Chittenden. The couple was responsible for the installation of many of the iconic features in the home, including the Georgian-esque lion door knocker and the stone wall that stretches along Park Avenue and Gadsden Street. The stones used for the wall had originally been used as ballast on a sailing ship from Scotland, and once discarded, were acquired by Chittenden by means of trade.

Amanda Hunter

In later years, the Chittendens had a son who grew up and, coincidently enough, married
F.H. Flagg’s granddaughter, thus bringing the home back into the Flagg family.

Ann Chittenden is the current owner of the home and oversees some of the operations of the Park Avenue Inn. According to Bruner, this isn’t the first time Chittenden has opened the home to paying guests. In fact, the building was remodeled and converted to an inn in 2003. Chittenden ran the inn with her aunt until 2009, when the untimely death of her partner led to its closure. 

Bruner approached Chittenden with an offer to reopen the inn.

“Our children are graduating school, and we decided a change would be good,” Bruner says. “I have always enjoyed touring old homes in small towns and in Charleston and Savannah and hoped to live in and care for one myself. I researched the idea and found that Tallahassee had only one B&B, and that started my endeavor. I run the inn much like Ann and her Aunt Nut (as she was referred to by family and friends) ran it.”

The inn offers accommodations in five different rooms of the house. Two are suites. All rooms come with private bathrooms, flat-screen TVs, Wi-Fi and complimentary breakfast. 

The rooms’ original furnishings accent the inn’s history. However, simplicity is key, says Bruner.

“The rooms are furnished with Chittenden family antiques and heirlooms, but I deliberately made sure each room was still open and not fussy or overloaded with furniture,” Bruner points out.

From the street, it’s easy to see why Flagg was captivated by the home. Its grand front pillars create an elegant platform for the wraparound porch, where guests of the inn can be found sipping coffee and reveling in the pleasant Southern climate. Dark blue shutters compliment the overall color scheme of the home while adding a bit of traditional Southern style. It’s believed that the front windows of the home, along with the ones in the living room and some of the bedrooms, had previously been used in the original territorial capital that was demolished in 1839.

The Park Avenue Inn sits within close proximity of many Tallahassee popular attractions. Guests can reach the Capitol Museum on foot in about 10 minutes or enjoy a leisurely stroll in nearby Cascades Park. The Avenue, a restaurant known for its seasonal Southern fare, is a two-minute trot across Monroe Street and provides a perfect ending to a day filled with Southern elegance.

“I’m very encouraged by the variety of clientele I have been able to attract, including several international guests,” Bruner offers. “My first guests were from Germany. They were visiting Tallahassee and walked by the inn and asked if they could stay. I am also thankful that residents of Tallahassee have used the inn for date nights and staycations. My guests are visitors touring Tallahassee, FSU parents, business travelers and legislators. My business neighbors have been most supportive in referring their clients to the inn.”  

Park Avenue Inn also functions as a wonderful event space for small wedding receptions, anniversaries and baby showers. The drawing room features 12-foot ceilings and is adjacent to the dining room which is available for catered events.

“We just booked a wedding rehearsal dinner that will be held in the backyard in April 2016,” Bruner notes. “And we booked a Masquerade Ball for October, too. I’m happy the community is aware of the inn and is using it for special functions.

“My goal is to run the inn for another 20-plus years,” Bruner says. “There are so few of the old antebellum homes left in Tallahassee. The Chittenden house is a piece of Tallahassee history, and she deserves to be loved and cared for as the Chittenden family has for generations.”

Categories: Homes