Midsummer Day’s Dream Ice Cream

Donkey pulls ice cream cart in 1963

Midsummer Day’s Dream Ice Cream

You may remember buying ice cream from an ice cream truck as a kid. As you think back, can you hear in your mind the familiar music when the truck was blocks away from your house? The neighborhood ice cream truck was fun, but I bet you never bought ice cream from a cart that was pulled by a donkey! That would have doubled the fun.

This story is about two Ashland teenagers and their summer dream job, in the year 1963 or 1964. The story is told by Richard Kreisman, who grew up in Ashland. Richard and his friend Gary Pennington inherited the donkey and cart from a buddy who had used it in Ashland the year before – then “graduated” to driving an ice cream truck route in Medford.

Richard remembers answering questions like these as they clip-clopped around town. 

            “What’s the donkey’s name? … Donkey.” 

            “What does Donkey eat? … Iced hay.”

            “Why do you do this job? … We get to eat the leftovers.” 

            “What do you do when Donkey poops? … Here’s a shovel, I’ll show you.”

Here’s how Richard set the scene: “The donkey and cart lived on a very small farm in south Ashland, where we put the two together for our regular route thru Ashland. This task included loading hay and water for Donkey, lunch for ourselves, assorted ice cream bars and dry ice, plus a utility pack of bucket, broom and shovel.”

Richard described how he and Gary shared the duties. “During our day we would alternate our tasks. One of us would be the driver and the other would be the pilot. When Donkey went poop, the driver would stop and the pilot would pile it into the bucket [which you can see in the photo].” 

As the donkey led them through the streets of Ashland, most of their customers were young children. Richard thought the parents had as much fun as the kids, pretending “that they were just tall children who carried wallets.” 

In 1963, the Oregon Shakespeare Festival season consisted of 47 performances at the outdoor Elizabethan Theatre, most likely from late July until early September. This means that actors would have begun rehearsing in early June. At the time, their primary rehearsal space was also the outdoor theater. The summer energy of Ashland was centered right here.

Elizabethan Theatre in 1961
This is a 1961 photo of the 1959 Elizabethan Theatre stage. (photo by Dwaine Smith, courtesy of Oregon Shakespeare Festival)

Richard remembers that their time selling frozen goodies probably started in late June and ended in late August. As entrepreneurs, and as teenagers, they were drawn to the energy of the Shakespeare Festival. Some of the energy came from the OSF acting company, which brought an eclectic, untamed spirit to this still mostly traditional town of about 10,000 people. More energy flowed in with tens of thousands of theater lovers, who came to Ashland even then from all over the country. Richard remembers the actors “wolfing down ice cream during early rehearsals when multiple performers would descend upon our traveling snack bar.”

Donkey pulls ice cream cart in 1963
This is the famous ice cream cart and donkey of Richard Kreisman’s memories. Either Gary Pennington or his brother Craig are shown in this photo.

8 Comments
  • Susan Kapteyn Matthews
    Posted at 17:45h, 19 September Reply

    So excited to see my family’s name spelled correctly. Thank you, Richard Kreisman !! (from Susie Kapteyn)

  • Ron Redding
    Posted at 15:49h, 18 September Reply

    I remember this very well. My dad at this time worked at the Cloverleaf Dairy for the Kapteyn’s. I sat next to Richard who played trumpet in the AHS band.

  • Dixie Hannon
    Posted at 11:07h, 18 September Reply

    The donkey cart came by our street on Lit Way nearly everyday in the summer. It was an awesome treat for 4 young kiddos.

  • Darryl & Alice
    Posted at 09:10h, 18 September Reply

    Thanks for another fun moment in Ashland’s history Peter.

  • Paige Jensen
    Posted at 07:18h, 17 September Reply

    Someone continued the tradition after these two teenagers because I absolutely remember buying ice cream from the donkey pulled cart ( I too grew up in Ashland) but it would have been mid to late 60’s or early 70’s. Thanks for the fun reminder!

  • Julie Woosnam
    Posted at 23:00h, 16 September Reply

    I recognize that cart and remember buying ice cream bars from you guys! I must have been in second or third grade. Didn’t the cart have bells on it, or am I making that up? Thanks for the photo.

  • Andrea Good
    Posted at 19:07h, 16 September Reply

    And, I love the name of their cart! Midsummer Day’s Dream!

  • Andrea Good
    Posted at 19:05h, 16 September Reply

    It must have literally been the ice cream dream for these kids! Thanks for sharing!

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