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Top Things to Do in Tennessee’s Oldest Town

May 11, 2026
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Whether you are visiting for a weekend getaway or just passing through for the day, you will find plenty to enjoy in a town rich with history and artistic charm. From guided tours and antique shopping to theatre performances and art galleries, Jonesborough offers something for those who appreciate culture and creativity.

Founded in 1779, Jonesborough is Tennessee’s oldest town, with a rich heritage that is still visible today in its preserved architecture and historic charm.

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The First and Last Town in Tennessee, Original Play Commemorates 250 years of American History as Told Through Local Storie

February 3, 2026
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The McKinney Center will debut a new play in February that is 250 years in the making. The First and Last Town in Tennessee shares stories from Jonesborough’s past and present to commemorate America’s Semiquincentennial. Written by Program Manager Anne G’Fellers-Mason, the play takes the audience on a journey from 1779, the year of Jonesborough’s founding, to present day.
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Valentine’s Day in Jonesborough: Chocolate, Dinner, Movies, Flowers & Community

January 22, 2026
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Nothing says Valentine’s Day quite like chocolate. Jonesborough Chocolate Fest is a must-visit for couples, friends, and families. Downtown merchants fill Main Street with chocolate treats, desserts, and specialty items. Enjoy sampling sweet creations while strolling through historic downtown and soaking in the festive atmosphere. Get your tickets now at jbochocolatefest.com
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