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Southside Village Guide

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southside 1In the shadow of Sarasota Memorial Hospital, between Osprey Avenue and Tamiami Trail, Hillview Street runs through the heart of Southside Village. It’s a highly walkable, centrally located Sarasota neighborhood featuring an alluring assortment of live music venues, restaurants, pubs and markets. The businesses cater to residential regulars as well as part-timers and tourists.

The Five O’Clock Club, established in 1955, remains the linchpin of the nightlife scene in Southside Village. It’s the place party people from Bradenton to Venice and beyond go for live music, libations and dancing. Owner George Generoso has ran the Five O’ since 1996; he also organizes the village’s largest annual event, the Giving Hunger the Blues charity concert.

“It’s extremely safe here and well lit,” Generoso says about the appeal of the neighborhood. “You can just park your car, hit a bunch of great restaurants and end up at the Five O’Clock Club and dance the night away.”

Knick’s Tavern and Grill has been a popular Southside Village spot since opening in 2002. The menu teems with clever comfort foods. The intimate room also has a bar serving wine, beer and a special sense of camaraderie.

“It’s such a great neighborhood and all the residents keep us afloat through the summer,” says Knick’s co-owner Knickole Barger.

Libby’s Café + Bar opened in 2008 and quickly established itself as one of Sarasota’s most beloved restaurants thanks to its imaginative, modern American menu featuring diverse dishes executed with uniform precision. One of the best happy hour deals in town also helps with Libby’s popularity, but go for lunch or dinner any time of the year and chances are you will find a cheery crowd enjoying the warm, dark wood interior or seated alfresco along South Osprey Avenue.

“As far as Sarasota goes, people kind of break it down into Siesta Key, downtown and St. Armands but this small great neighborhood is one of the best in Sarasota,” says Patrick Seidensticker, co-owner of Libby’s. “It’s the best of both worlds; right off the beach and a mile from downtown. For the past five or six years it seems to get better and better and we’re proud to be part of the growth.”

Check out or list of  Southside Village’s restaurants and bars, and see the neighborhood's upcoming annual events below.

UPCOMING EVENTS
The 14th Annual Firehouse Chili Cook Off: Sarasota firehouses will compete for chili bragging rights at this event that will also feature live entertainment and celebrity judges. All proceeds benefit Sarasota Firefighters Benevolent Fund. 2-5 p.m. Oct. 20; Morton’s Gourmet Market, 1924 S. Osprey Ave. #100, 955-9856, mortonsmarket.com.

The 3rd Annual Southside Village SECA Car Show: Car entries, sponsorships and vendor food sales benefit The Life of Riley Foundation at this free event. 11 a.m.-3 p.m. Nov. 3; Hillview Street, thelifeofrileyfoundation.org

Giving Hunger the Blues: One of Sarasota’s greatest block parties, Giving Hunger the Blues fills most of Hillview Street, providing fun activities for the whole family including outstanding live music with attendees paying a mere $5 admission charge, which goes straight to charity. George Generoso held the first Giving Hunger the Blues in the back of his Five O’Clock Club in 1996. Since then, the annual event has raised more than $1 million for the All Faiths Food Bank, which distributes about 88,000 meals weekly in Sarasota and DeSoto counties. March 23; Hillview Street, givinghungertheblues.org

Last modified: February 19, 2014
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