Silly’s History

My name is Colleen Kelley and I consider myself  extremely fortunate to have purchased a Portland Institution like Silly’s from the Nice sisters.  I took over in  November of 2002 and in that time have made some changes, however I have tried to preserve Silly’s as a fun, quirky feast for the eyes and the stomach in honor of the founders.  Thank you Deirdre and Stephanie for founding such a wonderful place…..

With that said I know that Silly’s opened on July 15th 1988 at 147 Cumberland Ave (now the home of Katie Made Bakery) and it moved to Washington Ave (built in 1909) its current location in 1997.  There are pictures of both buildings and a little history just inside the front door on the left. I emailed Deirdre Nice trying to find out more about the history of Silly’s and here is her reply….

“Well, Stephanie and I went to Jamaica back in November of 1987. We had been operating Prouts Neck Variety for two years and were looking around for a place we could operate all year and make our fast Abdullah’s. Stephanie was working at Sam’s Harbor Lunch and I don’t think I was working anywhere at the time. I called her up at work and told her we were going to Jamaica and to tell Sam she’d be back to work in 5 or 6 days. I packed and picked her up and we got on a plane. Those years at the Prouts Neck were grueling, we knew we weren’t going to do it again and were on the lookout for a new spot and interesting food but we needed a quick vacation.”

“While in Jamaica we discovered Jerk Chicken and brought it to Portland. We also came across a place called Bongo Cily’s. Cily was the woman’s name. A little place with great food, music that sort of thing.”

“About a month or so after we got home we found the spot on Cumberland Avenue in late December and signed a lease for it in January. Our rent was $125 a month. Gary Merrill, the actor, had gone to Florida and told us to stay at his house out by the water in Falmouth. So we camped out there for the month of February and started to think of names for the new place (which we eventually opened that July.)”

“We thought of everything under the sun, but at some point talked about the trip and the Bongo Cily’s place came up and Stephanie said how about Silly’s? It sounded right and that’s how it came about. After moving to the new place in 1997, we ran a pizza joint at the old place that we named Bongo Pizza. So the trip all those years ago still hadn’t worn off.”

outsidelight“Silly’s has been a magical name. It makes everyone feel good and has a different meaning for different people. I don’t think for Stephanie and me that it ever meant we thought what we were doing was silly or that we were silly or anything, but over time it simply allowed us (and now you) to do just about anything you want because it doesn’t constrict. It doesn’t mean anything and it means everything. “

Elvis shrine at sillys

Some more things from Colleen……

Bumper Sticker Club

You will see Silly’s bumper sticker in all the pictures on the wall.  The Nice sisters started this and I continue with its popularity by giving out bumper stickers to new guests and those who talk about going on a trip.  Guests’ email and drop off pictures throughout the year at which time I frame them place them on the wall.  I encourage participation and I am thankful for all new pictures that arrive because it means they were thinking of us at one of their happiest times and that is humbling.

Silly's inside 2005My hopes for Silly’s are to continuously update the menu and décor, to stay fresh, and to become a “green” restaurant.  All of these will take a lot of adjustment and hard work but will definitely be worth it.  Please understand and embrace change because it happens frequently within these 4 walls.

The motivation for Silly’s is… to be a destination dining location for all.  To provide wonderful service catered by unique people in an atmosphere of positive energy, whimsy and relaxed intensity coupled with food that is fresh, simple and delicious.  Please feel free to email me anytime with questions, comments or something you would like me to consider making on the menu or just to say hello.  Thank you for coming to Silly’s and I hope you enjoy yourself.

– Colleen Kelley, Owner

My deepest gratitude…..

To my mother Barbara “Bunchy” Gegg-Kelley, my father John “Big John” Kelley, my sister Michelle “Shelley” Kelley and my grandmother Anne Gegg Thank you for helping and supporting me every moment of everyday and making it possible for me to own Silly’s.

Thank you to my old management team Rich and Frank for teaching me so much.  To my friends, co-workers & educators, old & new who have worked here, come to visit, brought in new guests, talked it up, voted for Silly’s, given suggestions, told me when I need to pay attention, donated decor and offered the shirt off their back to help me.  You know who you are and I am forever humbled by how fortunate I am to know you.

To my staff old and new….Simply put…. Silly’s would not exist without the amazing talents of you.  Thank you very much for working here, for your wonderful suggestions, for your patience, for caring and for your integrity, you have made what is sometimes absolutely impossible to deal with possible.

A special thank you to Dave Cousins you are a genius web designer and Trena Penney for making this website possible.  Thank you doesn’t seem like it is enough for the time and thoughtfulness you put into this website and for being such a positive influence at Silly’s.

Sincerely, Colleen