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@The Clarke-Avera House Bed and Breakfast in Monticello, circa 1890-- -Cody Cruver Photography

Azaelas and well-preserved homes decorate Dogwood Street.

Monticello

Located 23 miles northeast of Tallahassee, Monticello is the quintessential small Southern town, where Spanish moss dangles from majestic live oak trees that shade the streets, antebellum homes grace the neighborhoods, and a quaint downtown invites visitors to dine and shop at family-owned stores and cafés.

As the county seat of Jefferson County, Florida’s only county without a single traffic light, Monticello offers an unhurried pace and friendly atmosphere. Its eerie history and reputation as “the South’s most haunted small town” make Monticello the perfect place to embark on a chilling ghost tour and even book a room at a reportedly haunted — yet delightful — bed and breakfast.

In Monticello and Jefferson County, visitors can explore Florida’s great outdoors, both in town and on the rivers and preserves nearby, from city parks and trails, including Monticello Ecological Park, Monticello Community Garden, and the Monticello Bike Trail, to the pristine Wacissa River and other waterways. Families of all ages will enjoy airboat tours on the river and visiting with the friendly animals at Aunt Louise’s Farm, which has special events and seasonal activities in the spring and fall.

History buffs will delight in Monticello’s collection of historic buildings, including the 1890 Monticello Opera House, which can be during a self-guided walking or driving tour. In June, the city celebrates one of the area’s most important crops with the annual Monticello Watermelon Festival, a multi-day event that includes a watermelon crawl, pageant, dancing, antique car show, and variety of family-friendly entertainment.

Plan your trip at Visit Jefferson County.