Letters from the Drinking Town #4 – Leo’s Ristorante

Dear Worcester,

Leo’s is a neon sign on Shrewsbury Street. It’s a fancy curlicue sign with red letters that states “Leo’s.” It makes you think of old times on the shore with the family back when men wore hats. That’s all it ever was for me in the near two decades I have lived in and around Worcester. An art installation more than a restaurant.

The restaurant proper is a few hundred paces back away from the street. I never felt the need to go there. I never heard of anyone recommending it. The only thing I might have been told is that it used to be a great old school Italian place but now the kids are running it and it’s not what it used to be. You hear that thing all the time. “The kids don’t have the heart the old man had for the joint.” That has been said as long as there have been family businesses. It doesn’t mean that it is true.

I have had no desire to try it out for the gin and tonic tour. Maybe because every time I mentioned it, people would pshaw it and say it ain’t worth it. So I skipped it when I hit 144 places for gin and tonics and the world did not break asunder.  I came back to do the new bars and restaurants last year and Leo’s didn’t even cross my mind. Now here I am on the third go round of bars in Worcester and I figured that I might hit the places I overlooked or ignored. While sitting in a doctor’s waiting room, I made a list of joints to hit and get a gin and tonic. For some reason, I caught myself writing down Leo’s. And so that is how it happened.

At 6:45 on a Wednesday (during restaurant week) I parked the car and walked down what felt like a back alley to the front of Leo’s. I wasn’t sure. I felt like a lobby to a forgotten hotel. I found the door and on my right was the mostly empty dining room. Greeted me was a mass produced sign that said, “Seat yourself.”

Okay, call me a snob. But if I want to seat myself, I will get my dinner at a food truck and find a nice bench to rest upon. If I am going to a restaurant that is not known to be cheap, I want someone to greet me at the door with pleasant efficiency. I want them to look at the table chart and find me the best and proper table. I want a smile and a, “This way please.” Is that so much to ask?

Apparently so. No one even acknowledged my confused presence.

I had to navigate the strange old setting myself. I looked down a short hallway and thought it was a good bet there might be a bar there. The pictures on the wall were family portraits, the owner and his wife I guess. It was more like going through a hallway in a friend’s family house, looking for the bathroom then looking for a place to have a drink.

I did find the bar and had an eight dollar gin and tonic. Do I have to even state that it was okay at best. The bartenders seemed preoccupied. There were three couples there at the bar, all eating and drinking. None of the food looked appetizing. They were just pasta with red sauce glopped on it like it was an Italian Restaurant themed horror movie: On Top of Satan’s Spaghetti!!!!

Outside of one of the bartenders, I was the youngest one there by about two decades. And I’m in my late forties. No one was excited to be there. It was the day to go out eating and so they were. I tried to think of something to write about but was stymied. The place is a tired joint filled with tired people.

To make my point, the bathroom has an ad on the wall for Charlton Manor Rest Home/ Assisted Living. I’m not knocking it, they know the right place to advertise. The copy reads in part “We are a small elegant home with many special feature, you will feel like you are visiting a Bed and Breakfast or an Old Inn.” Which is different from the feel at Leo’s – the Neon Sign that Walks Like a Dining Location.

On the wall of the bar area was a large painting that no doubt was purchased at Home Goods. It had a young stylish woman in a black dress at a bar. The bar was classic wood and was inviting. The view was from behind. Her head was turned so you spied her in profile. She held a martini glass aloft. She seemed poised and pleased. I thought to myself, “Why can’t I go there?”

Well that was snarkier than I thought it would be.

Until next time,

Dante of Worcester


2 thoughts on “Letters from the Drinking Town #4 – Leo’s Ristorante

  1. I went there with my family in the spring of 1992. I remember the date because it was my husband’s graduation. My parents had driven out from Amherst for the occasion and though the day had started sunny and in the 70’s by the afternoon a cold front had blown through and, as the outdoor ceremony finished up, the temp had dropped to the mere mid-50s. It was cold and we were cold and I remember asking for a cup of coffee along with a glass of red wine. I probably ordered the Eggplant Parmesan, a lingering culinary favorite, and remember thinking that it had been a good day. I’d had the forethought to bring a sweatshirt to the ceremony, my husband had a brand new MBA and my mother was in a relatively good mood.

    And that was the last time we ever ate at Leo’s.

    Thanks for jogging the memory. So glad you’re back Dante.

  2. Wow Uschi,

    What a wonderful memory. I like that aspect of restaurants. It isn’t the food but the people you are with and the things happening to your life. Thank you for sharing it with us here.

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