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The Pennington Family Books in Order

Part ofMay McGoldrick Books in Order

Find the Pennington Family books by May McGoldrick in order, with brief summaries, series background, and help choosing a starting point.

Last updated: July 14, 2026

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The Pennington Family books in publication order

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5 books

1

Romancing the Scot

by May McGoldrick

2017

Widowed war hero Hugh Pennington finds an unconscious woman hidden in a shipping crate at his Scottish estate. Grace Ware is fleeing murderers and hiding a dangerous secret, but safety at Baronsford may not last.

2

Sweet Home Highland Christmas

by May McGoldrick

2017

Gregory Pennington is assigned to escort Freya Sutherland and her young niece to the family's Christmas ball. A wintry Highland journey gives two guarded strangers a chance at an unexpected holiday romance.

3

Dearest Millie

by May McGoldrick

2018

Millie Pennington finally meets Dermot McKendry, the Highland doctor who may be exactly what her busy family life has been missing. Their story is a warm, romantic return to Baronsford and the wider Pennington clan.

4

It Happened in the Highlands

by May McGoldrick

2018

Jo Pennington and Captain Wynne Melfort search for the truth about Jo's birth parents. Their trail leads to an ancient abbey turned asylum in the Cairngorm foothills, where danger and long-buried secrets wait.

5

Sleepless in Scotland

by May McGoldrick

2018

Phoebe Pennington and Captain Ian Bell are drawn together while still haunted by the murder of Ian's sister. Finding love means facing the grief, suspicion, and unanswered questions that refuse to stay in the past.

The Pennington Family books in chronological order

  1. Book cover for "Sweet Home Highland Christmas"

    Sweet Home Highland Christmas

    by May McGoldrick

    2017The Pennington Family, Book 1
  2. Book cover for "Romancing the Scot"

    Romancing the Scot

    by May McGoldrick

    2017The Pennington Family, Book 2
  3. Book cover for "It Happened in the Highlands"

    It Happened in the Highlands

    by May McGoldrick

    2018The Pennington Family, Book 3
  4. Book cover for "Sleepless in Scotland"

    Sleepless in Scotland

    by May McGoldrick

    2018The Pennington Family, Book 4
  5. Book cover for "Dearest Millie"

    Dearest Millie

    by May McGoldrick

    2018The Pennington Family, Book 5

Series background & context

The Pennington Family series follows an extended Scottish aristocratic family through the Regency era. The books combine romance with family history, murder mysteries, war shadows, hidden identities, and the awkward fact that relatives tend to notice everything.

The main sequence opens with Romancing the Scot. Hugh Pennington, Viscount Greysteil, is a war hero and widower who has lost much of his taste for life. Then a shipping crate arrives at his Scottish estate carrying an unconscious young woman. Grace Ware is fleeing the killers who murdered her father, and she hides behind a claim of lost memory while she tries to recover and understand who can be trusted. Their attraction grows alongside a threat that reaches into British political life.

Baronsford holds a lot of secrets.

Sweet Home Highland Christmas is a shorter holiday story set around the Pennington family's annual Christmas ball. Gregory Pennington is asked to escort Freya Sutherland and her young niece from the Highlands to Baronsford. The trip gives two wary people a chance to see each other differently, with winter weather and family celebrations adding to the pressure.

In It Happened in the Highlands, Jo Pennington and Captain Wynne Melfort search for the truth about Jo's birth parents. Their investigation leads to an old abbey that has become an asylum in the foothills of the Cairngorms. The book keeps the series' mix of romantic connection and a larger mystery that needs solving.

Sleepless in Scotland centers on Phoebe Pennington and Captain Ian Bell. Their growing relationship is complicated by the murder of Ian's sister and the old grief that still surrounds the crime. The final listed story, Dearest Millie, gives the youngest Pennington sibling, Millie, her own long-awaited romance with Highland doctor Dermot McKendry.

The series is tied to the earlier Scottish Dreams novels through Lyon and Millicent Pennington, whose children and adopted daughter lead these later books. You can read the Pennington Family titles on their own, but starting with Romancing the Scot makes the family connections and the setting at Baronsford easier to follow.

These are romances for readers who like a big household, a little danger around the edges, and couples who have to sort through more than simple misunderstandings. The emotional center is always the same: people looking for safety, belonging, and someone who will stand beside them when the past comes calling.

Read in order for the fullest family experience, and save Sweet Home Highland Christmas for a quick seasonal stop between the longer novels.

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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