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Out and About in Winchester - Visit Winchester Kentucky
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Out and About in Winchester

Singers, songwriters and scouts take over the calendar for things to do in May in Winchester, kicking off with the return of one of downtown’s favorite gatherings: the four-concert summer Rock The Block Series.

May 13, 7-9 p.m.Rock the Block Series: Local family court judge Kimberly Carter lays down the law and the rhythms in opening the series. Joined by her husband (a retired local judge) on the guitar and other musicians, she’ll be holding court on the courthouse steps on Main Street. Pack a lawn chair to set up in front of the courthouse or grab a seat on the high side of Main for an evening of music, dancing and community fun.

Rock The Block is free, as is the bounce house for kids. A classic car show will be presented on North Main Street by Remember When Cruiserz. Food truck deliciousness, snow cones and “adult beverages” will be available for purchase. Plan time to visit downtown’s shops and restaurants before the show. 

Mark your calendar for this night and for the series’ other summer dates: June 1 features local musician Lauren Mink; July 8 brings in one of Kentucky’s hottest dance bands with Lexington-based Boogie G and the Titanic; and August 12 hosts Florence, KY-based Tom the Torpedoes, nailing that “vintage Petty sound” with the music of Tom Petty and the Hearbreakers.

May 22, 5-7 p.m. HeartStrings SongWriters’ Circle at Abettor: Singer/songwriters take the spotlight during this free event that is hosted by Winchester musician Trish Torline and held at Abettor’s North Highland Street location.

This “in the round” style music showcase features all song styles and musical genres – rock, folk, country, pop, Christian, alternative, R&B. The event gives artists a chance to workshop their material and melodies, tweak lyrics and share the stories behind the songs with the audience in an intimate setting. Who knows? You may here the Next Big Hit!

HeartStrings SongWriters’ Circle takes place on the second and fourth Sundays of the month. The lineup includes a rotating group of Kentucky artists and food trucks.

May 28-29 – Spring Trade Days at Fort Boonesborough: Plan to spend some of the Memorial Day Weekend at a gathering of merchants, traders, artisans, Native Americans, militia members, longhunters, scouts and other frontier characters at the original fort site of Daniel Boone and settlers.

“They will have camps set up that guests can visit,” said Park Manager Jack Winburn. “The merchants will be featuring eighteenth century wares that can be purchased and we will also have our regular living history demonstrations of pioneer skills.”

This event, which takes place throughout the day on both Saturday and Sunday, typically features period music and a chance to compare what life was like for the people who lived and worked the land, built a settlement and a community 245 years ago.

Fort Boonesborough has been reconstructed as a working fort complete with cabins, blockhouses and furnishings. Visitors can also tour the Kentucky River Museum (open Saturday during Trade Days) for a peek into the past of the lives of families who lived on the river and worked the locks and dams in the 1900s.

NOTE: During Trade Days, visitors are requested to park in the lower Fort lot on KY388 and ride the free shuttle up to the Fort.

Make it a Winchester weekend with a stay in one of several unique lodgings, including a Historic Log Cabin in a country setting and a downtown Carriage Inn apartment with views of the county courthouse. Winchester has a dozen or so brand name hotels and one-of-a-kind places for a fun getaway in the Birthplace of Beer Cheese.