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One of Monticello's most prominent historical buildings, the Monticello Opera House, is a working theatrical venue, with regular performances offering culture and entertainment in a small-town environment. Concerts of every genre, adult theatrical productions, children's theatre, a holiday sing-along and New Year's Eve Extravaganza ensure there is truly something here for everyone. With a theater on the second floor and a restored banquet hall on the first floor, The Monticello Opera House is also a popular reception facility for weddings, reunions and organizations.

Jefferson Arts is the local arts association that features a monthly art show in the gallery. Workshops and classes in various art media are held throughout the year. The group also sponsors school outreach programs and exhibitions. A gift shop featuring the work of Jefferson Arts members is open during gallery hours.

Many family-fun events are held throughout the year. April is the kickoff month for the two-day Southern Music Rising Festival with food, arts and crafts. During the June, the Watermelon Festival features activities from sports to the arts. The festival features arts and crafts, food vendors, a parade, a golf tournament, a children's theatre production, a barbeque dinner, a classic car show and a street dance with a live band. As Halloween approaches, the season for Historical Ghost Tours arrives. The Big Bend Ghost Trackers host a walking tour of the most haunted buildings in downtown Monticello. December brings the popular event Downtown Christmas held on the first Friday night in December. Enjoy the holiday season with Christmas music, crafts, cook-off, cakewalk, Santa Claus and children's performances. Ending the year with a big bang, Monticello rolls out the carpet for the New Years Eve Gala at the Monticello Opera House with dinner dancing, a stage production and loads of fun.

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