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Road to the Breaking Books in Order

Part ofChris Bennett Books in Order

Explore the Road to the Breaking books by Chris Bennett in order, with concise summaries, Civil War series background, and reading guidance.

Last updated: July 14, 2026

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Road to the Breaking books in publication order

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10 books

1

Breakout

by Chris Bennett

2021

Nathan and his former Texas soldiers are trapped at Mountain Meadows as pro-Confederate militia close in. Elsewhere, Evelyn's Underground Railroad shelter is threatened, forcing both of them to fight for the people depending on them.

2

Enigma

by Chris Bennett

2021

Nathan Chambers returns to Virginia to inherit a plantation and confront the human cost of slavery. As secession rumors spread and a family feud turns dangerous, he meets the guarded Evelyn and searches for a way to follow his conscience.

3

Insurrection

by Chris Bennett

2021

Civil war has taken Nathan's home, and he is torn between reenlisting for the Union and helping create West Virginia. Guerrilla violence spreads across his new community while his old enemy, Elijah Walters, moves dangerously close.

4

Invasion

by Chris Bennett

2021

In spring 1862, Nathan and his men stand in the way of Stonewall Jackson's drive toward Washington. Evelyn's spy network uncovers vital Confederate plans, but getting the information to wary Union leaders may prove just as dangerous.

5

Road to the Breaking

by Chris Bennett

2021

In early 1860, Captain Nathaniel Chambers leaves Fort Davis after his father's death sends him home to Virginia. A family plantation, a violent neighbor, and his hatred of slavery force him to choose what kind of man he will become.

6

Sedition

by Chris Bennett

2021

With Virginia nearing secession in 1861, Nathan fights to keep his state in the Union while enemies plot violence against him. Evelyn's work with the Underground Railroad draws her into espionage and a choice that could cost her everything.

7

Emancipation

by Chris Bennett

2022

As the Union war effort falters in 1862, Lincoln prepares to make emancipation a national aim. Nathan fights in western Virginia while Evelyn seeks Lee's battle plans, and the coming Battle of Antietam threatens to change everything.

8

War

by Chris Bennett

2023

In 1863, Nathan's regiment faces Confederate attacks in the Shenandoah Valley, while captured comrades plot an escape from Richmond. Evelyn faces a deadly counterintelligence hunt, and the freemen from Nathan's farm fight for their place in the Union Army.

9

Inferno

by Chris Bennett

2024

After a Union defeat in 1864, Nathan enters a hard campaign in the Shenandoah Valley under General David Hunter. Evelyn faces renewed danger in Richmond while Tony and the freemen prepare for a secret mission against Confederate defenses.

10

Resolve

by Chris Bennett

2025

As the Civil War reaches its final months, Nathan risks a mission into Richmond to rescue Evelyn and gather intelligence. With Grant pursuing Lee and Elijah Walters seeking revenge, the long conflict becomes a final fight for Nathan's family.

Road to the Breaking books in chronological order

  1. Book cover for "Road to the Breaking"

    Road to the Breaking

    by Chris Bennett

    2021Road to the Breaking, Book 1
  2. Book cover for "Enigma"

    Enigma

    by Chris Bennett

    2021Road to the Breaking, Book 2
  3. Book cover for "Sedition"

    Sedition

    by Chris Bennett

    2021Road to the Breaking, Book 3
  4. Book cover for "Breakout"

    Breakout

    by Chris Bennett

    2021Road to the Breaking, Book 4
  5. Book cover for "Insurrection"

    Insurrection

    by Chris Bennett

    2021Road to the Breaking, Book 5
  6. Book cover for "Invasion"

    Invasion

    by Chris Bennett

    2021Road to the Breaking, Book 6
  7. Book cover for "Emancipation"

    Emancipation

    by Chris Bennett

    2022Road to the Breaking, Book 7
  8. Book cover for "War"

    War

    by Chris Bennett

    2023Road to the Breaking, Book 8
  9. Book cover for "Inferno"

    Inferno

    by Chris Bennett

    2024Road to the Breaking, Book 9
  10. Book cover for "Resolve"

    Resolve

    by Chris Bennett

    2025Road to the Breaking, Book 10

Series background & context

The Road to the Breaking series begins in early 1860, when Captain Nathaniel Chambers is serving at Fort Davis in the west Texas wilderness. News of his father's death calls him back to Virginia, where he must protect his mother, face an old family enemy, and decide what to do with the plantation he stands to inherit. Nathan's opposition to slavery makes that inheritance a personal and moral trap from the start.

His journey home sets the tone for a big, continuing Civil War story. Bennett follows Nathan from the tense months before secession into a country breaking apart, where political arguments can quickly become threats, raids, and open fighting. The books move through Virginia, Richmond, western Virginia, army camps, battlefields, and divided communities whose residents must choose sides.

Nothing stays simple for long.

Nathan is a former army officer who knows how to act under pressure, but he is also trying to build a life that matches his conscience. His wish to free the people enslaved on his property and to resist secession puts him in danger from neighbors, local militias, and rivals who see his loyalties as betrayal. The personal feud at the heart of the opening books grows alongside the national conflict, giving the series both an intimate enemy and a much larger war.

Evelyn Hanson provides another important point of view. Drawn into the Underground Railroad and then Union intelligence work, she faces the risks of moving information, protecting vulnerable people, and operating in a society where a wrong word can bring terrible consequences. Her connection with Nathan adds romance and emotional stakes, but both characters have work to do beyond their relationship.

As the series continues through Enigma, Sedition, Breakout, Insurrection, Invasion, Emancipation, War, Inferno, and Resolve, the scope widens with the Civil War. Military campaigns, espionage, the struggle for West Virginia, emancipation, and the cost of leadership all become part of Nathan and Evelyn's path. The story is chronological and works best when read in order, since conflicts and relationships carry forward from one book to the next.

Expect a historical adventure with a serious moral center. There are battles and escapes, but also family obligations, political maneuvering, and people trying to claim freedom or protect the people they love in a nation coming apart.

Edited by

Richard Reis

Software engineer whose passion for tracking book recommendations from podcasts inspired the creation of MRB.

Anurag Ramdasan

Lead investor at 3one4 Capital whose startup expertise and love for books helped shaped MRB and its growth.

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