Flag House Inn

table set with place settings, fireplace in background

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About Our Historic Accommodations in Downtown Annapolis, MD

The interesting history of the Flag House Inn

The two townhouses comprising Flag House Inn were built in 1879 by a Welsh shipbuilder, Richard Owen Williams, and served a number of roles through the years. Descendants of the original builder say it passed through several generations of their family well into the 20th century. Each house in the duplex was individually owned, and we have traced the ownership in State Archives/ property records back to the 1920’s.

The two townhouses eventually became boarding houses, we have been told by several visitors that occupants were typically young ladies known as “drags” in Navy slang, and the male Midshipmen would call on the ladies in the sitting room. No visitors allowed upstairs! This type of arrangement faded over time, as women were admitted to USNA starting in the mid 1970’s and now make up ~30% of each class. At other times, the houses were owned by families.

In 1992, Tom & Connie Teigen owning #26 Randall St purchased #24, made significant renovations to open up the interior, modernize the plumbing & electrical systems, and harmonize the exterior siding and converted it into a bed and breakfast. Previously, the two homes looked very different. Recently (June ’21), the grandson of the Teigen’s stopped by, phoned his father and Tom was with them! He told some great stories: 4a wakeups to proof croissant dough, Connie going to the bank with money stuffed, well, on her body (!) and he confirmed they started flying the flags of their guests. See this recent video about this tradition.

In 1997, Charlotte & Bill Schmickle purchased the properties and ran the inn for 21 years, developing it into the well-appointed B&B that guests will experience today. It has been decorated with love and attention to historical detail. Every item in Flag House Inn has a story behind it! Bill & Charlotte were very gracious with handover and are doing well, living nearby.

Since early 2018, Flag House Inn has been owned by Marty & Carmel Etzel, who have entered the business after careers in the corporate/Tech (Marty) and education (Carmel) worlds. They bring their many experiences from personal & business travel, property management, marketing and knowledge of Baltimore, Washington DC and the Eastern Shore, and can make many recommendations on what to do in and around Annapolis.  Both spent significant time around the Chesapeake Bay growing up.

While keeping the traditional decor that’s appropriate to downtown historic Annapolis, they are working on modernizing many aspects of your experience such as room amenities, breakfast, and starting new traditions.  We are the caretakers of this lovely house until the next owners come along.

See this short video about our inn.  Many of our past visitors greatly enjoyed their stay with us, see the reviews from past guests in Trip Advisor or Google.  We recorded an in depth podcast in Feb 2021 with a local media service, it was a lot of fun to talk about our experience.  Listen here

More Stories

We’ve been contacted by many people with a connection to the house

– A retired CNO (Chief Naval Officer, head of Navy) who called on his future wife at one of the houses.

– Another former mid who called on his future wife in the 70’s (the proprietor said to the boys “See this line, none of you boys are coming across it!” )

– A man who grew up in #24 (Inn side) in the 70’s (the current Chesapeake room was his bedroom) who told many fascinating stories of the improvements made to the house – his electric supply was an extension cord fed thru a hole in the floor from 2nd floor, the previous layout of the kitchen, how the floors were jacked up and so on.  It was clear the original house had fallen into disrepair years back.  “Chuck” shared some pics, including one of him at the fireplace mantel 43 years ago.  When he visited us, he brought along that same painting, and we have restored the painting to its rightful place… See some pictures below!

– Also, the grand daughter of Helen Stinchcomb has visited with us.  Helen owned the #26 (owners side) from 1967 to 1983, and was famously the boarding house owner who warned the mids no one goes past her line.  Helen’s grandaughter  visited in September 2020 and brought old photos , shown below, as well as many stories.  It was fascinating to have her describe the previous layout, it was quite cramped!

People on steps

Front steps # 26 this is reversed image – its from a slide


Helen Stinchcomb, owner of #26 Flag House Inn 1967-1983

Lady in front of garden

Helen Stinchcomb in front of shed now garage)

Young man in front of fireplace

“Chuck” lived in #24 Randall with his family in 70’s & 1980″s – this is him in front of fireplace in Merchant Marine Academy uniform

man standing by fireplace

“Chuck” lived at #24 Randall in 70’s & 80’s, above mantel is same painting where he was photographed 43 years earlier

little girl standing by sailboat

Back yard of #24 Randall in 1970’s before it was bricked over for parking

little girl sitting n sfront steps

Front of #24 Randall in 1970″s

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