We meet at the Fun Shop, climb steep stairs, cross a room overflowing with merchandise, duck through a doorway, go past children's toys, clothes, and books and finally arrive at his photography studio. "When we first came to Middleburg fifty-five years ago my wife Nancy opened the Fun Shop down the street and I opened my photography studio here. Then we merged. I've been losing space ever since," says Howard Allen. His studio is cozy, bathed in the diffused soft light of photographer's umbrellas. Mr. Allen takes a seat on the bench where he poses his clients for portraits. An ecru colored paper is a uniform background. The chair he has directed me to is positioned where I would guess a photographer would stand to take his picture.

So, how did you get to Middleburg? "Well, it wasn't a direct route," Mr. Allen says. "I was born in Berryville, grew up in Winchester, served in Africa and Italy during the war - as an ambulance driver. When I returned home I went to New York to study at the Art Students' League. I always liked drawing, especially caricatures," he pauses to show me his collection of caricatures.

"Anyway, I married Nancy, a home-town girl, in 1948 and we moved to Washington where I got a job with the Washington Post as an artist in their promotion department. But I tired of the 9 – 5 drill, and when my boss told me about a job with a photography studio in town I grabbed it. I stayed there for 3 years covering visiting entertainers like Frank Sinatra and Louie Armstrong and Washington notables like Eleanor Roosevelt. You know, back then you could walk right up to the stage and take your pictures – no security people held you back.

"One day my old boss at the Post called and asked if I would do a photo shoot in Middleburg. While I was out here, I discovered that the local photographer had died and his business was for sale. The rest, as they say, is history."

Howard Allen pauses to ask if it would be okay if he told me the rest of his story in photographs. Next to him on the bench is a pile of 8 X 10's face down.

He flips up the first photo, "Here is Arthur Godfrey giving an exhibition on his horse Goldie at the Upperville Horse Show. You know who this is," he states as he flashes the familiar face of media personality Willard Scott. "And here is a local Middleburg celebrity, Joe Fargis. He became an Olympic gold medalist in individual and team show jumping." The pictures show Willard Scott with hair and Joe Fargis taking a jump at age 10.

There are the typical Middleburg photos: fox hunting; steeplechase racing; and children in riding habit. Some capture graceful riding scenes. Some catch spectacular falls. One photo shows a rider flipping over a fence and landing headfirst in a mud puddle. Mr. Allen quickly flips to two more of the same rider, moments later, covered with mud but apparently sound and smiling.

As a preamble to the next picture he states, "This was taken on their first date here in Middleburg". He flips up a picture of Senator John Warner with Elizabeth Taylor. The next photo is of the movie actress dealing Black Jack at a Middleburg's annual Casino Night charity event. "Yes, she was really as beautiful as everyone said and friendly to everyone," he smiles.

And then we get to his favorite pictures, the ones he took of the Kennedys when they rented Glen Ora, an estate a mile outside of Middleburg. "Jacqueline kept her horses here and she and the children visited often. Our daughters and Caroline Kennedy were in the same pony club, so we saw them quite often," he says.

When the Kennedys were at Glen Ora, they went to church at the Middleburg Community Center (there was no Catholic church in town then). "One of my vivid memories is of Sundays when all the Washington photographers came out to take pictures of the family going to church. They used my dark room, and you would see these guys all running around waving their wet pictures in the air trying to dry them before driving back to Washington."

"I was honored in 1962 when Mrs. Kennedy asked me to take the official birthday picture of her with the children." He flips over a picture of the First Lady riding her horse along a country road holding John on her lap with Caroline riding her pony along side. "This picture appeared in media all over the world. Sometime later I got a call from the editor of McCall's magazine who said she had Jackie's permission for me to sell her one of the other pictures I took that day – they ran it on the front cover."

Howard Allen flips to a picture of an older Jackie riding with Pamela Harriman, and says sadly, "She came back to Middleburg every year to fox hunt right up to the time she died."

His photo pile is empty. Fifty-five years is a long time, how has Middleburg changed?

"When Nancy and I first came, there were only a half dozen stores in town. It was just a sleepy country village. I was on the Town Council in the '60's and we just went in, read the minutes and went home. Now everything's more citified," he says, "Our daughter, Betsy Davis, is the Mayor now. It's a big job!"

There are so many new people I hardly feel like I know anybody anymore. I never thought when we came here that we would stay for our whole lives. The Fun Shop has grown and grown – it's the oldest family owned shop in town. People say, 'If they don't have it at the Fun Shop, you don't need it.' Our daughters, Page Gloseclose and Betsy manage the store now. Nancy comes in just to check up on everybody."

Any regrets?

"Only one! That I didn't have my picture taken with President Kennedy when I met him."