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1. On Friday, May 27, the Annunciation Greek Orthodox Church will host the 43rd annual Greek festival. Held in Tremont every Memorial Day weekend, the popular event features Greek music, food, drink and even antiques. Visitors will find a mouthwatering assortment of homemade Greek specialties like pastitsio, moussaka (Greek style lasagna), dolmades (stuffed grape leaves) and lamb shanks. But the crowd favorite is always the gyro — and they don't get much better than they are here. Be sure to save some room for baklava or loukoumades (fried dough with honey). If you want something to wash it all down with try the Greek beer Mythos or some Greek white wine. The festival starts at noon and is free.
2187 West 14th St., tremontgreekfest.com
2. On Friday, May 24, Osteria di Valerio in the Warehouse District will throw a "Swinging Affair," when they transform the popular subterranean space into a Rat Pack den. Rick and Sharona will be belting out everything from Sinatra to Peggy Lee. The entire menu — including the famous gnocchi and risotto — is available. The event starts at 8 p.m. and is free as long diners eat and/or drink.
408 W. St Claire Ave., 216-685-9490, osteriacleveland.com
3. On Sunday, May 26, One Shift, a Boston fundraiser, will take over Whiskey Island Marina and Wendy Park to benefit the family of Martin Richard. Richard is the eight-year-old boy who sadly lost his life in the Boston bombings. "This will be an event like no other!" promises Rob Turkek, president of the Cleveland Chapter of the U.S. Bartenders Guild, the non-profit spearheading this event. Sponsored by Bacardi, Jack Daniels and Samuel Adams, this event is no cost to attend and will feature local food trucks like Touch Supper Truck, Umami Moto, and KRAV. Turkek is inviting any and all tipped employees to choose a shift to work and to donate their tips to for the cause. It starts at 2 p.m. and is free, but please tip generously.
2800 Whiskey Island Dr., 216-631-1800, oneshiftforboston.org
4. On Tuesday, May 28, Cowell & Hubbard in PlayhouseSquare will host the Cleveland Independents Bartender Competition finals. Regional Ohio bartenders have been showing off their creative cocktail talents throughout the month in hopes of making it to the finals. According to chef Jonathan Bennett of Red Restaurant Group, and president of Cleveland Independents, "We're proud of these bartenders, and we're proud of our restaurants. We want to showcase both in every possible way." Starting at 5:30 p.m., the finalists will be judged by area celebrities such as Fox 8's Kenny Crumpton. The winning bartender will receive $400 in Cleveland Independents gift cards.
1305 Euclid Ave., 216-479-0555, cowellhubbard.com
5. On Wednesday, May 29, Behind the Woods Restaurant in Rocky River is hosting the Eat, Cook, Love, Laugh Dinner Party. The Italian-themed fundraiser will raise money for scholarships for teachers for character education. A $50 admission fee includes two drinks and a full dinner cooked by three guest chefs. Jim Chillemi of Dominic's in Westlake, Chad Chillemi from The Woods, and Cheech Vinciguerra of Lou's Italian Sausage Company will collaborate to prepare a three-course dinner. "These chefs bring their expertise of Italia to this event because Italy is too far away to drive to," says Janet Vinciguerra, promoter for event. An appetizer course includes an olive oil tasting station from The Olive Scene of Rocky River. Following the entree course, the dessert course will feature gelato provided by Rosso's in Rocky River. A silent auction along with live entertainment from Dom & Russ will also be provided. Reservations are required.
21919 Center Ridge Rd., 440-333-9663