Indulge at Chocolate Fest
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
Get creative at a Hot Cocoa and Paint Community Event
Kick off Valentine’s season with a cozy and creative afternoon hosted by Heritage Alliance in partnership with the Washington County Public Library. The Hot Cocoa and Paint Community Event will take place on Saturday, February 7, 2026, from 1:00 to 3:00 p.m. at the Chester Inn Museum Parlor, located at 116 West Main Street.
Enjoy a Romantic Dinner Downtown
After a day of chocolate tasting or painting, settle in for a nice dinner at one of Jonesborough’s locally owned restaurants. From cozy dining rooms to elevated menus, downtown offers a variety of options perfect for Valentine’s Day.
Dinner and a movie at The Jackson Theatre
Make date night extra special with dinner followed by a movie or live performance at The Jackson Theatre, located at 121W Main St. This beautifully restored historic theatre offers a timeless and romantic atmosphere right in the heart of downtown and is the perfect way to end a Valentine’s evening.
Flowers from First Class Floral
No Valentine’s Day is complete without flowers. Stop by First Class Floral, located at 137 E Main St, to pick up a stunning bouquet for your sweetheart. From classic roses to custom arrangements, choosing flowers from a local florist adds a thoughtful touch while supporting a Jonesborough business.
A Valentine’s Dance for Seniors
Valentine’s Day celebrations in Jonesborough are for the whole community! The Jonesborough Senior Center will host its annual Valentine’s Dance on Friday, February 13, at the McKinney Center, located at 103 Franklin Avenue. Tickets are $7.00 per person and are open to both Senior Center members and non-members. Tickets may be purchased at the front desk of the Jonesborough Senior Center, located at 307 East Main Street.