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Angie Bryan

Angie Bryan is a former diplomat who is enjoying getting acquainted with her new home in Portland, one cocktail at a time.

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Posted: December 31, 2018

Lenny’s in Westbrook is a lively live music pub

Written by: Angie Bryan

A packed crowd filled the bar and kept servers busy at Lenny’s.
Photos by Angie Bryan

When my friends and I walked into Lenny’s, we discovered a cozy and friendly atmosphere. The bar was too crowded for us to fit in, so after checking to see whether there were purse hooks under the bar (there were), we sat down at one of the regular tables made of pressed tin ceiling tiles covered in glass.

Service was friendly (but could have benefited from an additional server – the place was hopping), and we decided to kick things off with some chicken wings, since it was a Wednesday, when a dozen wings are $10.50 – $5 cheaper than on other days. The wings come in six flavors, and you can order two flavors per order, so we got two dozen and chose blueberry barbecue (my favorite), Buffalo, salt and vinegar, and black pepper garlic. All were really tasty, with subtle flavors that didn’t destroy our palates.

Drinks from the cocktail menu at Lenny’s include the Manhattan, Limoncello gin and tonic and Old Fashioned.

Lenny’s has 10 specialty cocktails. I went for the $8 Limoncello gin and tonic. Unfortunately, I couldn’t taste either Limoncello or gin in it, so I left it undrunk on the table, and the server never asked if there was a problem. In her defense, she was really busy, but it did prevent me from ordering something else. My drinking companions had the $11 Manhattan and the $8 Old Fashioned. Both were average. One friend then ordered the $9 Westbrook Rye cocktail (rye, apple, cranberry and bitters), a light and fruity concoction and our favorite drink of the night.

Wings come in six flavors and are cheaper on Wednesdays.

For food (because two dozen chicken wings aren’t enough), we went with the $5.50 cup of French onion soup on special, the $13 Irish nachos (made on potato chips instead of tortilla chips) and the $12.50 sweet potato salmon burger with a $2 up-charge for a side of onion rings. The onion rings were spectacular, with an extra-crunchy batter, but the rest of the food was just ordinary (although the nachos got a lot better once we began dipping them in the house-made blue cheese dressing that came with the chicken wings).

Lenny’s is just as much a music venue as it is a pub, and jazz/pop keyboardist Darrell Morrow was onstage the night we were there. The crowd appeared to be heavy on middle-aged regulars, many of whom seemed to know the staff and/or musicians, and some of whom sang and danced to the music. The music stayed at a reasonable volume, and at one point, Morrow invited a friend of his up to perform a few songs. His friend, the unforgettable Angie MacDonald, blew the crowd away with her voice – I know this is about the bar, not the music, but I am unable to refrain from commenting on how incredibly talented she is. Everyone in the bar was transfixed.

If I went back, I’d stick to what they do best – Wine and Wings Wednesday, when $20 buys any bottle of wine that is also sold by the glass.


WHERE: 1274 Bridgton Road, Westbrook
PHONE: (207) 591-0117
HOURS: 3:30-10 p.m. Tuesday through Saturday, 3-8 p.m. Sunday. Food served 5-9 p.m. Tuesday through Saturday and 4-7 p.m. Sunday.
AMENITIES: Large parking lot, kitchen that cooks everything from scratch and sources its ingredients from local places like Pat’s Meat Market, live acoustic music and a social hour 3:30-5:30 p.m. Tuesday through Friday featuring $3 to $5 appetizers, $4 well drinks and $1 off draft beer. Wine and Wings Wednesdays offer discounts on chicken wings and bottles of wine.
BOTTOM LINE: Popular hangout for live-music lovers age 50 and up.

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