Bailey's Harbor Schoolhouse Inn
Bailey's Harbor Schoolhouse Inn
  • Home
  • About
    • History
    • Policies
    • Contact
  • Rooms
    • Garden
    • Library
    • Upper Deck
    • Principal’s Office
    • Lighthouse
    • Homestead
  • 2026 Reservations
  • More
    • Home
    • About
      • History
      • Policies
      • Contact
    • Rooms
      • Garden
      • Library
      • Upper Deck
      • Principal’s Office
      • Lighthouse
      • Homestead
    • 2026 Reservations
  • Home
  • About
    • History
    • Policies
    • Contact
  • Rooms
    • Garden
    • Library
    • Upper Deck
    • Principal’s Office
    • Lighthouse
    • Homestead
  • 2026 Reservations

Baileys Harbor District #1 Schoolhouse

108 Years of the District #1 Schoolhouse

Baileys Harbor Schoolhouse Inn in 1917

1917

A plot of land belonging to Hedwig Peil (current owner Kristen Peil’s great-grandmother) is grouped together with neighboring plots and purchased by the Town of Baileys Harbor to build a school.


Architect Fred Crandall begins work on the newly commissioned schoolhouse .

Baileys Harbor Schoolhouse Inn In 1918

1918

Construction is completed on the Baileys Harbor District #1 Schoolhouse.

Baileys Harbor Schoolhouse class picture in 1935

Circa 1935

The schoolhouse operates with two classrooms, teaching grades 1st through 8th.


On the left, note Mr. Viste, the longest serving principal in the Baileys Harbor District #1 Schoolhouse.

Baileys Harbor Schoolhouse Inn Circa 1975

Circa 1975

 Kristen’s grandfather Roland Peil and father Loren Peil worked on the 1955 brick addition which can be seen across the front.


As class sizes continued to grow, a mobile classroom was also added to the south side (left) in the 1970s.

Last day of classes at Baileys Harbor Schoolhouse in 1983

1983

The last day of classes in the Baileys Harbor District #1 Schoolhouse.

Orphan Annie’s Gift Art Antiques at Baileys Harbor Schoolhouse 1987

1987

After housing the public library and town offices, The Town of Baileys Harbor offered the schoolhouse for commercial rental use.

 

Annie Peil, Kristen’s mother, moves her successful art and antiques business into the schoolhouse in 1987.

Annie Peil and Kristen Peil (mother and daughter) in front of their store at the schoolhouse

Circa 1990

Kristen Peil officially adds a vintage clothing boutique to her mother’s existing shop.

Loren and Annie Peil purchase the Baileys Harbor Schoolhouse 1994

1994

Annie and Loren Peil save the historic Baileys Harbor building from demolition by purchasing it from the town.


The first room is converted into lodging.

Previous owners Annie and Loren Peil at Baileys Harbor Schoolhouse Inn 2003

2003

Annie and Loren complete the renovation of the schoolhouse into a seven-room inn, completing a majority of the construction themselves.

Caleb, Kristen and Ida in 2016 at Baileys Harbor Schoolhouse Inn

2016

Kristen Peil and Caleb Whitney, along with daughter Ida, purchase the building in 2016.


The family continues to carry on the tradition of the hands-on ownership that has preserved the schoolhouse for the past 108 years.

Our Family Legacy and The Schoolhouse

Hedwig Peil

Hedwig Peil

Kristen Peil

Hedwig Peil

1st Generation 

(Kristen’s great grandmother)


Hedwig assisted with the school’s land acquisition in 1917 and served as the building’s custodial staff.


Roland

Roland Peil

Kristen Peil

Hedwig Peil

2nd Generation

(Kristen’s grandfather)


Roland spent his entire formal (1st-8th grade) education at the schoolhouse. He went on to work with the construction crew who built the brick addition in the 1950s.

Loren Peil

Loren Peil

Kristen Peil

Kristen Peil

3rd Generation

(Kristen’s father)


Loren attended the school and is the original lodging owner. After renting the space for many years, Loren along with his wife Annie purchased the schoolhouse from the Town of Baileys Harbor in 1994. As their “retirement” began so did renovations for Orphan Annie’s Schoolhouse Inn.

Kristen Peil

Kristen Peil

Kristen Peil

Kristen Peil

4th Generation 

(Current Owner)


Kristen attended school in the original building and ran a vintage clothing boutique alongside her mother Annie Peli’s antique store in the schoolhouse during the 90s. 


Kristen and her husband Caleb bought the property in 2016.

The Schoolhouse Inn Today

Current owners Caleb Whitney, Kristen Peil, Ida Whitney selfie

Fourth and Fifth Generation Authenticity

The 1917 schoolhouse has been a part of our fifth-generation Baileys Harbor family since the acquisition of the building’s land in 1917. Today, Kristen Peil, Caleb Whitney and their daughter Ida Whitney take great pride in continuing the family legacy through hands-on ownership and operation of the inn.

Historic photograph book of Baileys Harbor District #1 Schoolhouse Door County WI

Historic Photograph Book

 The current owners Kristen Peil and Caleb Whitney published a pictorial timeline of the District #1 Schoolhouse! Starting back in the early days of 1862, construction blueprints, decades of class photos and generations of businesses are all recorded.

 

By curating this collection, Kristen and Caleb hope to encourage others to share their stories about and photos of the schoolhouse.

Learn More
Bouquet Photography Book by Ida Whitney at Baileys Harbor Schoolhouse Inn Door County WI

Bouquet Photography Book

Caleb and Kristen’s daughter Ida has been photographing the schoolhouse for over half a decade. She published this small coffee table book featuring the inn’s garden-to-table bouquets.


A small keepsake for all who have fallen in love with the inn and its gardens, just like her.

Purchase Your Own

Baileys Harbor Schoolhouse Inn

reservations@baileysharborinn.com

+1 (920) 839-5353

Copyright © 2025 BH Schoolhouse LLC - All Rights Reserved.

We value your privacy.

We use minimal cookies to analyze website traffic and still optimize your website experience!

Accept