Wealth of Seasonal Charm: A Look Inside Chestertown’s Historic Bolton House

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In the heart of every historic Eastern Shore town there’s a prime street where the homes are remarkably distinct, character-rich, and narrative driven. On such a street in Chestertown you will find our feature home on a block well known for its venue as a fine stroll dotted with wrought iron fences, sumptuous plantings, and welcoming front porches. 

Historical Pedigree

This property’s particular narrative dates back to the Revolutionary War era when Chestertown was one of the busiest port towns in Maryland—second only to Annapolis—bustling with shipments of tobacco and wheat, and the natter of the day was consumed with the war effort. Into this mix, came a patriot and one of the very Sons of Liberty for the Eastern Shore, John Bolton. An appointee for the Commissary of Kent County, Bolton was a key supplier of ammunition for the colonial military. It was Bolton who sanctioned the construction of the original residence that dates back to 1759. 

Today, this meticulously maintained and historically preserved three-bedroom dwelling is home to a husband and wife best suited to its continued stewardship and loving care. All year-round the home of Susan Flanigan and Michael McDowell is particularly distinguished due to its richly red painted exterior and pride of place on a primary town corner. It is at this time of year, however, when the residence takes on a particular glow and a wealth of seasonal charm that says the holidays have arrived in Chestertown. 

The first exterior cues that yuletide celebrations are in the offing are the window displays that Flanigan conceives and tends throughout the season. A dedicated member of the local garden club, Flanigan’s handiwork is not only seen, but enjoyed aromatically throughout the home. 

“Outside the house, I decided to use flowerboxes which are wired to eye-hooks to hold them in place,” explains Flanigan.

Inside those boxes is a fragrant mix of nature’s resources, many plucked or snipped from their own backyard gardens.

“I love the use of berries,” she says, which have been added to what she describes as base greenery, such as boxwood, and other detailed pieces such as blue spruce. “Then, I sprayed some pods gold and layered in pyracantha and holly, to gradually build up the color and texture.”

Each window of the home is then lit in the colonial style with one single white candle. The porch of the home, supported by four stately Doric-style columns, was added in 1780, says Flanigan. It is accented with a railing of intricate wrought iron from which now hangs an ornate swag of both artificial and real greens intwined with ribbon, pine cones, orange slices, red berries, and white lights.

Most notably when surveying the exterior of the home one notices that another historical property, The Dunn House, was added on in 1786, when William Dunn purchased the Bolton house and added on to it initially with just one room and then several more over the years. It now functions as two, separate private residences.   

The first time Flanigan and McDowell walked across the threshold of their home was 2017, when they had decided that it was time, after thriving D.C.-based careers in education and journalism, respectively, to retire somewhere that would keep them within the confines of the Chesapeake Bay. The region, a place with great meaning to Flanigan, who grew up vacationing at her family’s summer home north of Gibson Island. 

“I’ve always been very soulfully attached to the Chesapeake Bay,” says Flanigan. 

For McDowell, a Fellow with New America, a policy and research-based thinktank based in the District, Chestertown reminded him of what he enjoyed most growing up in Belfast, Northern Ireland—a walkable town with bricks underfoot, welcoming storefronts, and friendly local business owners that were just a jaunt away. The pair are nostalgic preservationists who have worked closely with the Maryland Historical Trust to ensure that whatever they might want to do to make the home their own was historically appropriate and sanctioned. 

Making It Their Own

One of the first matters to be addressed by the couple regarding the exterior was the result of a unique discovery in the home’s front hall. Upon inspection they found a secret panel in the wall near the entry. Once opened, it revealed what they learned to be the original color of the home when Bolton lived there. 

“The color of the house was white when we purchased it,” explains Flanigan. “Then we looked in that secret panel in the front hall and we saw that the original boards [were painted] a deep red.” (This special spot in the entry is now marked for historical reference with a print of artist John Hesselius’s portrait of the original owner, John Bolton.)

This episode in the homeowners’ history still amuses them, she says, as the painting project did not go off without a hitch and actually caused quite the stir in town when the first coat of the new hue was applied.

“The painters put one coat over the white, and when you put one coat of red over white, what do you get?” 

Flanigan says she clearly remembers returning from an establishment in town that afternoon to see the bright pink result of that first layer of paint and was in a panic, as was the rest of the town who had yet to learn the owners had no intention of keeping it that way. 

“And then we got the second coat on, and I told the contractor it was still not deep enough, so we went to three coats of paint and now we have that nice, deep, red color.”

Deep, forest green shutters would accompany the rich red wood boards completing the cosmetic portion of the exterior changes to one of the oldest wooden houses in Chestertown. (Several weightier exterior improvements, including replacing the roof, subsequently needed to be made as well, and were all accomplished with the counsel of the Maryland Historical Trust.) 

The warmth of wide-plank pine floors and a winding center hall staircase wrapped in greens, white lights, and the couple’s collection of official White House Christmas ornaments beckons further entry and provides glimpses into the home’s library on the right and front living room to the left. 

The library with its stately Federal-style fireplace over which an elephant Audubon print is displayed and flanked by a set of nostalgic, period built-ins, would be deemed the annual location of the couple’s primary Christmas tree. Flanigan relays that she often displays several throughout the house, and that they prefer locally sourced fresh trees cultivated without the use of pesticides, so that they can then responsibly recycle them to a nearby farm for goats to enjoy after the holidays.

This room is accented and trimmed in a delicate, pale green and made all the more precious for its collections of keepsakes; none more treasured than the military sword resting next to the tree against the fireplace surround. This particular saber belonged to their son, Marine troop commander, 1st. Lt. H. Conor McDowell, who gave his life for his country during a training exercise in May of 2019 at Camp Pendleton. He was just 24. Other loving remembrances of Conor, such as the clothes pin ornament of a soldier that Conor made as child suspended from branch on the Christmas tree, are placed with care about the home in his honor, and we gratefully acknowledge his and their sacrifice. 

That pale green color of the “Jane Austin” room, as Flanigan sometimes refers to the library, is a holdover from the home’s previous owner and long-time Chestertown resident, Mackey Dutton. The hue is inspired by a cherished line of Famille Rose dinnerware handed down on Dutton’s maternal side of the family. 

It would be remiss to talk about this home without mentioning the contributions of Dutton and her late husband, Fred, who stewarded its continued renaissance after a long period of neglect in the 1980s. In 1989, a group of committed preservationists were credited with stabilizing the structure, and carefully removing all of the integral period features such as its original chestnut beams, chair rails, and cornices, and meticulously replacing them after an entirely new utility systems package was installed. Once updated, it served as the Dutton residence for many years.  

“The house as we purchased it from Mackey Dutton was very much in move-in condition,” says Flanigan, who remarked that there were several antique furnishings and decorative items from the Dutton collection that live on in the house today, including some found in the front room of the house to the left of the entry hall.

This room is the cozy place where the couple enjoys reading and warming themselves by the home’s original fireplace mantle and surround to which they have added the efficiency of a wood-burning stove. The family pooch, Rosie, is ever resting at the foot of their Knoll sofa. This room also conceals a hidden treasure behind a set of built-in doors, in the form of an old-fashioned bartender’s keep, complete with a nook to make and stir cocktails, and places to store their mixers and spirits. 

Flourishes and Other Finery

No holiday season would be complete without a festive feast or perhaps just a nosh, and that would be most splendidly accommodated in the couple’s formal dining room at the heart of the home. This space, so cheery and bright, with its original chestnut beams overhead and wide pine planks below is the consummate entertainers’ space. A cherished Flanigan family heirloom dining table is set for the proceedings with an exquisitely stitched tablecloth, the handiwork of a member of her local church, and crackers, not to eat, but the British yuletide tradition, as an homage to her husband’s roots in the U.K.

This room also boasts a handsome mantle and a wood-burning fireplace that Flanigan says they sought the help of a local craftsman to create since the room was not furnished with one. The exact replica of the mantelpiece design found in the front room is the work of carpenter Dick Swanson.

“And he did it in such a way that it looks like it was always there,” adds Flanigan.

Above the table is a crowning touch, another handmade creation, this one crafted by Flanigan, a wreath woven into the existing structure of the chandelier above of fresh boxwood greens and a selection of Christmas balls handsomely painted to depict scenes from the 12 Days of Christmas.

In addition to Flanigan’s passions for the garden and literature, the art of the miniature also plays dare we say, a larger role in their home.

This aspect is uniquely conveyed upstairs in the home’s primary bedroom. 

“I have always loved doll houses,” explains Flanigan. “I wanted to display my little miniature furniture but didn’t have a space for a doll house. So, I created a space in our bookshelf and put some paper on the back of the shelf to create a wallpaper effect, and I added in the little evergreen to make it Christmas-y.

She also adds holiday flair to the display with the tiniest of themed fireplaces and a prized hand-blown, glass Christmas tree that she acquired on a trip to Winterthur Museum, Garden & Library.

With all this attention to detail, it is little wonder that this residence has previously been a stop on the town’s Holiday House Tour, an event that Flanigan reflects upon fondly. 

“As hosts on the ‘Dickens of a Christmas’ house tour, we brought that history to life for our visitors. Like Scrooge in A Christmas Carol, we hope to honor the spirit of past, present, and future Christmases here and keep it in our hearts the year round,” Flanigan says. “We consider ourselves stewards of Bolton House. Our home belongs to the historic fabric of Chestertown.”

For information regarding this year’s Dickens of a Christmas events in Chestertown, visit mainstreetchestertown.org.

Flanigan’s Tips for Flawless Seasonal Florals & Greens

Nothing adds to the festivity of the season quite like using fresh greens with their complementary seasonal scents. Fortunately, floral enthusiasts like Flanigan know there is a knack to working and she agreed to share some tips:

1. To keep her boxwood wreath arrangement above the dining room table looking and smelling its best throughout the holiday season, Flanigan says she always keeps a spray bottle filled with water handy and gives the arrangement a healthy spritz daily.

2. A good rule of thumb when creating fresh floral arrangements, such as a window box, is to view it from different angles to ensure that there is a good measure of height in the middle or center of the arrangement with a gradual tapering down and draping of greenery out and over the sides of the boxes. 

3. Did you know that one of florists’ most relied upon arrangement tools, Oasis, is also one of the most detrimental to the environment? Flanigan notes that this green, block-like material is toxic and breaks down so slowly that good gardeners and conservationists alike are now looking for alternatives to using it. In her own work, she intends to substitute wire mesh in future window box arrangements to help reduce their personal environmental impact.