Booking It Through History: First Ladies – Dolley Madison

My Booking It Through History: First Ladies focus for April is the queen among the First Ladies – Dolley Madison. Dolley is the first First Lady to have the title and is the gold standard for even our modern First Ladies. With her charm and vivacious personality, Dolley brightened every room she entered and pioneered the use of social events to bring partisans together. She is a true American icon!

Each month, I’ll detail the life of the first lady and their legacy. Then I’ll share what I learned while studying them, along with ways you can travel in their footsteps through historical sites and museums. I’ll also share books, podcasts, TV shows, and websites where you can learn even more about that first lady. Read all of the way through the blog post or click on the links below to go straight to those sections.


Dolley Payne Todd Madison was born on May 20, 1768 in North Carolina to John and Mary Payne, Quakers who had recently moved to the state from Virginia. When Dolley was only a year old, they packed up their growing family and moved back to Virginia, settling in Hanover County near relatives that included Patrick Henry. Her father was a farmer near Henry’s Scotchtown, and Dolley spent her childhood helping her family with innumerable chores as the oldest daughter, growing close with her three younger sisters and four brothers. Even though they were kin to the “voice of the Revolution,” her father’s pacifism kept them out of the crosshairs of the British and also led to the emancipation of their slaves in 1783.

When Dolley was fifteen, the family left Virginia for the Quaker stronghold of Philadelphia, Pennsylvania. Her father attempted to become a starch merchant but his business failed in 1789, causing him to be “read out of meeting” by his fellow Quakers. This led to a debilitating depression and his early death in 1792. Dolley’s mother took on the responsibility of providing for her family, opening a boarding house frequented by congressional members in the nation’s temporary capital.

Inquisitive and erudite, Dolley was a striking young woman with black curly hair and sparkling blue eyes. Before his death, her father arranged her marriage to a local fellow Quaker, lawyer John Todd. After marrying at the Pine Street Meeting House on January 7, 1790, they moved into a new home (now the Todd house in Historic Philadelphia) and soon were joined by two sons, John Payne Todd and William Temple Todd. Dolley was a happy wife and mother and found a way to become friendly with the President’s wife, Martha Washington, even with her strict Quaker social mores. 

The summer of 1793 proved to be the end of this idyllic time in her life. As yellow fever swept through the city, John sent Dolley and their two small children to the countryside while he stayed to take care of his ailing parents. Within weeks, her husband, younger son, and in-laws all perished, leaving Dolley alone with a toddler to support. After fighting with her brother-in-law over John’s estate, Dolley was able to support Payne financially, but the emotional toll of this tragedy was hard to overcome. 

The following spring, Dolley was introduced to Congressman James Madison by her good friend, Senator Aaron Burr. While they were an odd pairing, Madison short and wizened, Dolley tall and full of life, they soon were a love match and married at Harewood, Dolley’s sister’s estate in Virginia on September 15, 1794. Since Madison was outside of the Quaker faith, Dolley was read out of meeting like her father. 

Stuart, Gilbert, Artist. Mrs. James Madison, Dolly Payne / from an original picture by Gilbert Stuart, in possession of Richard Cutts, Esq. M.D. Washington. , None. [Between 1804 and 1855] Photograph.

Dolley and James spent the first three years of their marriage in Philadelphia. Upon his retirement from political life in 1797, they moved back to Montpelier, James’ estate in Orange, Virginia. They spent just three years there during the Adams administration when James was asked to serve as Thomas Jefferson’s Secretary of State. James, Dolley, and Payne packed up and moved to the swampy new capital of Washington City where Dolley quickly became the center of all social events.

As I noted last month, President Jefferson was a widower, so Dolley served as his hostess when needed. With Jefferson’s republican sensibilities preventing many state dinners or receptions, the Madison home became the centerpiece of Washington entertainment. With Dolley’s keen intellect and social graces, members from both sides of the aisle were brought together in a friendly way. Dolley’s charm worked wonders with the diplomatic corps as well, preventing crises brought on by Jefferson’s temperamental nature. She also took on charitable projects, including raising funds for the Lewis and Clark Expedition.

When James won the presidential election of 1808 with Dolley serving as his campaign manager, she became the official hostess of the President’s House. She lost no time changing out Jefferson’s shabby bachelor furnishings, forcing Congress to fund renovations to make the home a source of national pride. James and Dolley presided over the first inaugural ball in the nation’s new capital with Dolley dressed in a regal cape with a train and hat with exotic feathers.

Even though Dolley didn’t dance due to her Quaker background, she became renowned for her hostess duties and hosted more formal dinners than any other First Lady in history! She also hosted drawing rooms every Wednesday evening that were so crowded, they were called “squeezes.” In her fanciful turbans and the latest Parisian fashions of empire-waisted gowns with her parrot, Polly, sitting on her shoulder, what a sight she must have been!

Dolley was popular with politicians, including her good friend, Speaker of the House Henry Clay. She befriended the wives of the politicians as well, corralling the women into “dove parties” to attend Congressional debates. She used her social connections to further James’ political gains, causing his opponent in 1808 to say that he had been “beaten by Mr. and Mrs. Madison…I might have had a better chance had I faced Mr. Madison alone.” However, jealous people, including her nemesis John Randolph, slandered her in the newspapers, questioning the Madisons’ marriage and Dolley’s faithfulness. 

Dolley was also the first First Lady to publicly support charitable causes, raising funds for the Washington City Orphan Asylum. In doing so, she set the tone for future First Ladies to choose a signature charitable cause, which still survives today. She also provided a home for her sisters, including widowed Lucy who remarried Supreme Court justice Thomas Todd. It was the first wedding at the President’s House.

After James’ reelection in 1812, the machinations of war with Britain began in earnest. Just over thirty years after the victory at Yorktown during the American Revolution, Britain still didn’t respect the fledgling United States and had been impressing thousands of American sailors for years, forcing them to serve in the British Navy against their will. The first two years of the war were tumultuous with James deathly ill at times and troops suffering humiliating defeats. During this time, Dolley served as James’ personal secretary when his official secretary was sick.

As the British Army marched towards Washington City in August, 1814, James left Dolley at the President’s House while he rode out to review the troops at Bladensburg. Dolley was determined to stay until he returned, but as the entire town fled, including the soldiers protecting her, Dolley made hasty plans to escape. She packed as many State papers as she could, foregoing many of her own personal belongings. Most famously, she instructed two enslaved workers to take down the famous Gilbert Stuart painting of George Washington and send it away for safekeeping. She fled to the Virginia countryside, cannons booming behind her every step. The British arrived shortly after she left, burning the President’s House, the Capitol, the Library of Congress, and many other public buildings. The only thing remaining of Dolley’s home was the charred walls.

Upon return to Washington, she and James moved into the Octagon House where they spent the next six months of his presidency. Although the treaty that ended the war only reinstated the status quo, the Americans believed they won the war. James was able to finish his presidency with Dolley hosting events at the temporary President’s House at the Octagon House and an additional home.  

Dolley and James must have breathed a sigh of relief to head home to Montpelier in 1817. They spent almost two decades together there where they hosted many famous guests including Thomas Jefferson and the Marquis de Lafayette. They also dealt with Payne’s many debts and misdeeds, always getting him out of trouble to their own financial detriment. James’ health began to falter, and Dolley rarely left his side. However, she had just stepped away when he died on June 28, 1836. Without her “Jemmy,” Dolley was heartbroken and suffered a physical and emotional breakdown. How terrible it must have been when she had to sell Montpelier (and the enslaved living there) to pay debts in 1844.

She moved back to Washington and lived at the Madison-Cutts house built by her brother-in-law on Lafayette Square. She depended on money she got from Congress for James’ State papers and on charity, including from a former enslaved worker who sent her some of his own money now that he was free. She was often visited by future First Ladies, was friends with eight presidents, and continued her political involvement with her own seat on the House floor. She lived long enough to lay the cornerstone for the Washington Monument (along with Eliza Hamilton!) and had several photographs taken of her. She was also chosen by Samuel Morse to be the first civilian to send a telegraph. She died in Washington on July 12, 1849 and had a state funeral attended by thousands, eulogized as the “first Lady in the land.” She is buried beside James at Montpelier.

Thanks to my good friend and Dolley expert, Libby McNamee, for contributing to this piece.


Dolley’s legacy is legendary as the founder of Washington, DC society. She is known for her wit, charm, and vivacity, a model of civility and empathy that transcended party and social status. By using her soft skills of diplomacy through entertainment, she showed the men in charge a thing or two about how to get things done without playing political games! Without her, I doubt there would have been a President James Madison. 

James and Dolley were an odd pair, but they were a true love match. While her first marriage was arranged by her father and she expressed some ambivalence about marrying James, Dolley grew to love her little “Jemmy,” and they had a bond that war couldn’t break. They were heartbroken to not have any children of their own and had to be disappointed in Payne’s debauched life. He never lived up to his potential, drinking away his own depression possibly related back to the tragic loss of his father. 

As First Lady, she left so many precedents that are still valid today. From her inaugural ball to her receptions to her charitable works, most modern First Ladies have looked to Dolley as a role model. The only comparable recent First Lady is Jacqueline Kennedy.

She is claimed as North Carolina’s only First Lady (to date!), but she considered herself a true Virginian. Her family’s legacy in Virginia was enhanced by her sister’s marriage to George Washington’s nephew. Her brothers, however, spent their time much like Payne – drunk and in debt, dying at young ages. One brother, Walter, was tragically lost at sea, adding to the long list of losses that Dolley endured.

Slavery was an issue that was unresolved in Dolley’s lifetime, and with her Quaker upbringing mixed with her life as a plantation mistress, it was unresolved in her own mind as well. She grew up with the enslaved that her father emancipated. Then as James’ wife, she was expected to lead a household made up primarily of the enslaved. Scholars have debated how she felt selling the enslaved to pay her debts upon James’ death, but it’s not clear.

Dolley is a prime example of rising above trials and tribulations, the ultimate positive cheerleader. She had some very hard times in her life – financial woes, losses of those she loved most, hurtful scandals – but she always looked on the bright side and pushed forward. It is an admirable quality!

My Time with Dolley

I loved reading about Dolley and couldn’t help but smile when learning about her parties with a cursing parrot and outrageous turbans! How it must have charmed both Federalists and Democratic-Republicans alike, causing them to get along with their political foes to be part of the social scene. She set the standard for Southern hospitality mixed with a regal presence that perfectly blended the American values of individualism and collaboration. 

I wish more politicians today understood the benefit of getting to know their opponents outside of the House or Senate floor, seeing how similar they are that could lead to common ground on just about any issue. We need a new modern-day Dolley to help usher in another era of gentility and civility.

In learning more about the First Ladies, I love to imagine them all in a room, discussing the highs and lows of the job. Dolley was friends with Mrs. Washington but never got to meet Mrs. Adams. I’d like to think they would all be bosom friends, with Dolley a perfect blend of Mrs. Washington’s empathy and Mrs. Adams’ political wit. She took the best from both and made the First Lady job a unique and needed thing in both political and social DC. As a former DC dweller, I appreciate all that she did to ensure the capital city became a true showplace that makes Americans proud to this day.

While her political life was full of success, Dolley’s home life was full of ups and downs. I can’t imagine her grief as she lost her husband and baby at the same time. How did she go on? Much like Martha Washington, there was no time to feel sorry for yourself when you had a young child to support. What these women endured is unfathomable to us today, and I admire Dolley’s tenacity and ability to pivot. 

As I walk the streets of Washington, DC, I’d like to think that Dolley would be thrilled at how it has turned out. From its sweeping vistas down the National Mall to the halls of power on Capitol Hill and the White House, our modern city that is the political capital of the world can give thanks to those in history who saw its potential, including Dolley.

What an amazing woman!

Travels with Dolley

Dolley didn’t travel much in her lifetime with her focus on the mid-Atlantic region from Philadelphia to North Carolina.

North Carolina: 

Greensboro History Museum – This history museum is located near Dolley’s birthplace and has an exhibit all about her. 


Montpelier – James and Dolley’s home is a wonderful place to visit to learn more about their life together. You can see Dolley’s unique way of entertaining and imagine her sitting on the porch looking out over the rolling Blue Ridge mountains.

James Madison Museum – This museum may be small, but it’s mighty! Just a few miles from Montpelier, it has many artifacts from James and Dolley. It makes a great stop before or after Montpelier.

Scotchtown – Patrick Henry’s home is near Dolley’s family farm and historians believe she visited here

Fairfax County – There are several historical signs about Dolley’s route while fleeing a burning Washington.

Washington, DC:

Octagon House – This temporary President’s House where Dolley and James lived after the burning of the official residence is open for tours. Thanks to my friend, Libby McNamee, for the pictures!

Dolley Madison House – This home at 1520 H Street, NW near the White House is where Dolley lived after James’ death. It is not open to the public, but you can see the Dolley-themed placard as part of the Star-Spangled Banner trail (and other signs around the park about Dolley’s heroic actions).

Smithsonian National Museum of American History – In its First Ladies exhibit, you can see several of Dolley’s dresses and china.

National Portrait Gallery – To see the actual daguerreotype of Dolley in her later years, visit this amazing art gallery.


Todd House – Dolley lived in several homes during her many years in Philadelphia, and her home with her first husband, John Todd, is preserved as part of Independence National Park. 

Madison home – Just a few steps from the Todd house, you can see a placard outside of the home (located at 4th and Walnut Streets) Dolley shared with James while the government was in Philadelphia.

West Virginia: 

Harewood – The home of Dolley’s sister, Lucy, and her husband George Steptoe Washington, this was the site of Dolley and James’ wedding. You can view the historical marker but the home appears to be private.

To Learn More

Books to Read:

All links are Amazon affiliate links. You can also purchase the books through my affiliate link to which supports independent bookstores.


A Perfect Union: Dolley Madison and the Creation of the American Nation by Catherine Allgor

This biography of Dolley and how her skills created our American identity is a good way to deep dive into her life. Allgor uses letters, diaries, and other primary sources to give you a good insight into Dolley’s life. She also discusses the politics of the day (especially during Jeffferson’s tumultuous years!) but those parts are easy to gloss over if you’re just looking for Dolley.

First Ladies of the Republic: Martha Washington, Abigail Adams, Dolley Madison, and the Creation of an Iconic American Role by Jeanne E. Abrams

This book delves into the three first First Ladies, Martha Washington, Abigail Adams, and Dolley Madison, and how they created the role of First Lady in the fledgling country. It’s a really fascinating read!

Mr. and Mrs. Madison’s War: America’s First Couple and the War of 1812 by Hugh Howard

For all of the details about the War of 1812, read this!

The Intimate Lives of the Founding Fathers by Thomas Fleming

I bought this book at the National Portrait Gallery and can’t wait to dive in. There are two chapters on Madison and his marriage to Dolley.


Dolley: A Novel by Rita Mae Brown

This historical fiction novel by the prolific Brown is an entertaining way to take in a lot of history. Brown described political and personal intrigue in the nation’s young capital and captures Dolley’s vivacity. It’s an older book so some things haven’t aged well, but it is a worthwhile read to learn more about Dolley.

Patriot Hearts: A Novel of Founding Mothers by Barbara Hambly

I am glad I waited until after learning about Dolley to read this book about Martha Washington, Abigail Adams, Sally Hemings, and Dolley Madison. Hambly does a good job at weaving their stories together in interesting ways, and she packs a lot of history into the book. If you’re looking for a fiction companion to the nonfiction First Ladies of the Republic book mentioned above, this is it! 

Kids’ Books:

For older kids:

Dolley Madison and the War of 1812: America’s First Lady by Libby Carty McNamee 

I adore this book by my good friend, Libby. It is written for upper middle grade/young adult readers but is a great read for adults as well. The propulsive story about Dolley’s famous quick thinking that saved George Washington’s painting will keep you enthralled to the very last word! And you (and your kids!) will learn so much history in a fun way!

For younger kids:

Women Who Broke the Rules: Dolley Madison 

A Picture Book of Dolley and James Madison

Dolley Madison Saves George Washington

Dolley Madison Saves History (Graphic History)


Here’s Where It Gets Interesting, Episode 171: Hello, Dolley!: How to Become the Icon of a Nation



The History Chicks 

The Past, The Promise, The Presidency Conversations

How We Got Here, Season 3, Episode 5

TV Shows

C-SPAN First Ladies: Influence and Image



UVA’s The Dolley Madison Digital Edition (subscription required but there is a free trial) – there is a free website with additional information as well

White House Historical Association

  • Also where you can purchase the official White House Christmas ornament in honor of both James and Dolley

C-SPAN First Ladies: Influence and Image

From a little girl growing up as a strict Quaker in rural Virginia to the toast of Washington society, Dolley Madison was the most famous woman in America during her time. She left a legacy of hospitality and good will that is still the standard for First Ladies and for all hostesses today. 

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