Milton-Freewater Through The Years: "The most unusual and interesting fact in Milton and Freewater's history."

Last Updated 2/9/2024Posted in Historical Preservation, #mfcda


Articles, Commentary, and Photos Courtesy of Marcia West Akes

This is probably the most unusual and interesting fact in Milton and Freewater's history.

1915 Photo from a Freewater advertising brochure. The building later became Crimins Barber Shop and was “wiped out” in the 1928 fire. The Freewater Times noted, “J. S. Crimins....salvaged most of his barber equipment.” The building was rebuilt and became Barnes Barber Shop in the late 1930s. Before Milton and Freewater consolidated, the boundary line that separated the two towns ran through the building. In an old article, Clarence Barnes stated, “I could give a man a shave in Milton and cut his hair in Freewater!” It became the famous “two-town” barber shop and was written about in “Ripley’s Believe It Or Not!” In the mid-1960s, the building was turned into a fabric store and is now the Umatilla County Extension Office (on the south corner of N. Main and N.E. 5th Street.)

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More on “two-town” barber shops

A few more details have been brought to light about the “two-town” barber shop. The line between Milton and Freewater ran through the building that was Crimmins’ Barber Shop until 1937, and Clarence Barnes was a barber there until it became a fabric shop in the mid 1960’s.

Gerald Stiller pointed out facts noted in the July 27, 1928 Freewater Times about the big fire. The article states that the fire “completely destroyed two blocks of the business section of North Milton, adjoining Freewater, early Sunday morning and for a time threatened the entire business and residential section of Freewater.”

When listing some of the business owners who were able to save some items, the article says that “J. S. Crimins, in the brick block on the corner of Main and Depot Street, salvaged most of his barber equipment.” Stiller points out that Depot Street then, is Main Street today. In 1928 the streets were slightly different than they are now and where at this time Depot Street “dead ends” by the old Milton train depot/current senior center, at that time it extended on down to the Freewater business district.

The 1928 article also states that “Thirty-Seven business concerns were wiped out” which included “two buildings occupied by Western Union Telegraph and Crimins barber shop.” Stiller has photos which show the difference between the old building and the one built after the fire. Also, a picture he has of the Freewater Barber Shop shows a door to a Western Telegraph. 

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(Picture of basketball player at Mac-Hi)

Jerry explained that the family name was spelled “Crimmins.”  However, when he was in high school his father changed the spelling to only have one “m” as there was another Crimmins in town and the post office kept getting their mail mixed up.  Jerry has now gone back to the original spelling of his family name, but that is why the huge basketball picture of him on the wall of the Mac-Hi gymnasium has his name as “Crimins.”   Jerry still holds the Oregon High School Single-game Scoring Record of 73 points, which he scored in a 116-63 Mac-Hi win over Hermiston on February 23, 1952.  He edged out three other players throughout the state and that year was recorded as “the most historic season of high school basketball that Oregon has ever seen.”

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Crimmins remembers “two-town” barber shop

By Jerry Crimmins, Mac-Hi Class of 1952

The February 13th issue (of the Valley Herald) contained an interesting front page story for me.  The article was titled “State Farm Insurance celebrates 44 years in M-F.”

Jim Burns says he was told that at one time there was a barber shop where the Umatilla County Extension office is now, on the corner of N. Main and N.E. 5th Street.  The line between Milton and Freewater ran through the building.  “You could get a shave in Milton and a shoeshine in Freewater,” it was said.

I heard this story when growing up in Milton in the 1930’s and 40’s, from my family members, many times.

The barber shop was owned by my grandpa, John Summerfield Crimmins.  It was called Crimmins’ Barber Shop.  Mr. Crimmins came from Huntington, Oregon in the early 1900’s, settled in a small house at the end of N. Main; near the then Federated Church building and across the street from the VanSlyke house, a large grand white residence.

Mr. Crimmins and his wife, Flora, had four children:  Dan, Jack, Carol, and Meredith.  They all attended school in the old Freewater grade school building and all graduated from Mac-Hi in the 1920’s and 30’s.  All are now deceased except for Dan who is now 98 years old and living in Moscow, Idaho; where he was City Treasurer for many years.

Mr. John Crimmins died suddenly of a heart attack in 1937.  What happened to the barber shop?

My father was Jack Crimmins who worked for F. G. Lamb and Company in the fresh fruit packing houses and later (after the great freeze in the valley in the early 1950’s) in the pea canneries and freezing plants.

My step-father was Al Beard whose auto parts store was across N. Main Street from where the barber shop was - mentioned in the article.

I live in the Portland area and have subscribed to the Milton-Freewater paper for many years; through good times and not so good….for the paper.

Gerald Stiller’s historical features are always interesting to me.

I am a 5th generation born in Milton, and even before it was Milton for my ancestors - my great great grandpa Brown arrived at the Cowl’s Crossing on the Walla Walla (River) in 1864 where great grandpa Daniel Frank Brown was born.  He later developed the area’s first electric company which he sold to the City for $5,000 about 1888.

(Following up on what happened to the barber shop located on the corner at 418 N. Main Street.  At this point, we are not positive who owned it after John Crimmins passed away in 1937, however, it has been said that Clarence Barnes was a barber at that location for 32 years.  Apparently, Barnes retired around the mid 1960’s, but he could have been an employee of Crimmins in the early years and been in the location for that long. 

Charlotte (Stewart) Trumbull notes that in the mid 1960’s she purchased the building from her grandfather Charlie Stewart’s estate.  She says he owned the building when it housed the famous “two-town” barber shop and it was written about in “Ripley’s Believe It Or Not!”

The building was empty when Trumbull took over in the mid 1960’s and she remodeled the entire building into a fabric shop.  She explains that the end section had the barber shop equipment still in it, that they had to tear out, and the rest of the building had been a Western Union office and a taxi office.

In the mid 1970’s Trumbull sold the building to the county, and former extension agent Debbie Lee says they moved the Extension Office to that location in the mid 1970’s; where it is currently located..)

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The Freewater Barber Shop

By Gerald Stiller

The Freewater Barber Shop was located on the corner at 418 N. Main Street.  Today the building houses the Umatilla County Extension Agent Office and the Water Resources Office.

Before the two cities of Freewater and Milton consolidated, the boundary line that separated the two towns ran through this barbershop.  Clarence Barnes was the barber and stated in an old article “I could give a man a shave in Milton and cut his hair in Freewater!”  Clarence barbered at this location for 32 years!

I remember getting my haircut in this shop at an early age.  Clarence put a board across the white arms of the magical barber’s chair and I climbed up to my make-believe throne.  Around my neck was placed a white robe that would keep the tickling hair clippings from falling down on me.  The first buzz of the clipper is somewhat startling, but not as bad as those scissors going snip-snip and the comment, “Don’t move!  Just about got an ear!”  Then came the finishing touch with hot steaming shaving cream lather applied to your neck to be shaved by a honed sharp razor.

I always found the trip to the barbershop interesting.  There was usually several people waiting and a lot of conversation (some gossip) about what was happening in local neighborhoods.  Some good stories were told I am certain, but few remembered except several heated political barbs!

I marveled how the barber would strop the leather strap to hone a sharp blade on that single bladed razor.  Then he’d begin to slide that blade across one’s whiskers that had been covered with steaming shaving cream.  Once I decided to try my father’s razor and soon decided that once was enough!     

The barber’s chair was a mechanical piece of art.  The barber had complete control and could jack you up higher and swivel you around in a complete circle and lay you down for a shave.


The red and white barber pole has become a symbol for a barbershop.  The pole represents the day of blood-letting in barbershops.  It is said that white bandages were used in the blood-letting process and then hung on a pole.  The wind wound the red and white bandages around the pole.  The pole then became the barber’s symbol for his shop.


Barbershops are also known for singing quartets that sang special harmony with song.  “Wick” Parrish was a barber in Condon, Oregon in the late 1950’s and sang and wrote Barber Shop Harmony Songs.  


Barber shop quartet singing began in the 1800’s.  It was a fun time for the men who usually sang around their community barbershop.  In 1947 women organized a ladies singing group called the “Sweet Adelines.”


Two early day barber shops mentioned to me were the Emmerson Barbershop and the Crimmins’ Barbershop.  In 1959 Glenn’s Barber Shop was located at 907 South Main in Milton.  In the 1980’s Earl Karr had a barbershop at 408 North Main where the Valley Herald Newspaper is located today.

(Blood-letting was the withdrawal of often considerable quantities of blood from a patient in the belief that this would cure or prevent a great many illnesses and diseases.  It was a tremendously popular medical practice up to the late 19th century.  Though the blood-letting was often recommended by physicians, it was usually carried out by barber-surgeons.)
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