Area Events


Every year Jefferson County adds more events for the enjoyment of everyone. Arts events abound with a rich harvest of theatre, many genres of music, art exhibits, crafts workshops and fun festivals. For the outdoor enthusiast, there are many events and tours for biking, canoeing, fishing or hunting. A wide variety of equestrian activities range from trail rides, to special painted pony parties to rodeo events to competitions. With the abundant rural nature of Jefferson County, this is a popular location to hold events that connect kids with nature. The Events Calendar is updated frequently with festivals, performances and activities, so check back often or sign up for our newsletter.

Upcoming Events

Tour of Homes - March 18, 2017

The Home and Heritage Tour is provided for the benefit of the Jefferson County Historical Association which sponsors projects and events focusing on the rich heritage of Jefferson County.  Come spend a delightful day in our town, and then you too can say, "I Found It In Historic Monticello!"  

The 13 stops on the tour this year are:

1.   Wirick-Simmons House  -    Jefferson County Historical Association Headquarters
      115 East Pearl Street
2.   Pasco-Merritt House
      710 West Washington Street
3.   The Daffodale House Bed & Breakfast
       635 West Washington Street
4.   The Avera-Clarke House Bed & Breakfast
      580 West Washington Street
5.   The Jefferson Arts Gallery
      575 West Washington Street
6.   1872 John Denham House Bed & Breakfast
      555 West Palmer Mill Road
7.   Monticello Ecological Park
      Entrance on South Water Street
8.   The Cottage Bed & Breakfast
      295 West Palmer Mill Road
9.   Murdock-Kirkpatrick House**For Sale**Sold**
      185 East Palmer Mill Road
10. Dilworth-Barnhill House
      345 East Washington Street
11. Budd-Carswell House
      555 East Washington Street
12. Shuman-Alexander House**For Sale**
      310 East Dogwood Street
13. Cornerstone Warehouse & Sales**Estate Sale**
      285 North Railroad 



Monticello Bike Fest April 1, 2017
Get your chain greased and  your bikes tuned up for the event.  Train, train, train to get your fastest time or be prepared to stroll through the prettiest county in Florida.  Join Jefferson County Chamber of Commerce for a morning of fun!  Ride 10, 30, 60 or even 100 miles - or just bring the family and enjoy a casual ride on a lovely spring day at your own pace.  Click here for registration and other information.
Want another reason to pedal the Bike Fest?  Upon registration participants will receive a $5 voucher for any restaurant or retail store in Monticello and also included at registration Friday night is an appetizer of chicken jambalaya, refreshments and live music located at Rev Cafe on the Courthouse Circle.

Emancipation Day Celebration
  • Monday, April 17th, 2016 10:00 AM - 3:00 PM
  • Add this event to your personal calendar
  • Join in the festivities planned for Emancipation Day! Call 850-997-3760 for more information

67th Annual Watermelon Festival  June 4 - June 18, 2017

The 67th Annual Watermelon Festival will be held on various dates in June.  See the schedule below for details on how you can participate, volunteer, enjoy, or become a vendor.  Call 850-997-5552 for more information.
June 3, Watermelon Pageants
June 9, Kick-Off Dinner, Bed Race, and Rodeo
June 10, Rodeo
June 15, Woman's Club Fashion Show
June 16, Rotary Barbecue & Street Dance
June 17, FMB Breakfast, Antique Car Show, Parade & Festival

Lighting of the Christmas Tree Downtown Monticello December 1, 2017

Starting at 2 PM wonderful, beautiful decorations will go up on the first block of East Dogwood and part of Cherry Street. At the intersection of Cherry and Dogwood a tent will be set up for Santa who will arrive on a huge red LOUD fire truck. People will take photos of their little ones sitting on Santa's Lap.
Soon Vendors will start arriving with their tents., They will open tables and fill them with goodies such as baked goods, especially the Monticello Women's Club fabulous homemade fruitcake. Some will offer interesting jewelry, plants, scented candles, oddities and books for Christmas gifts. Local non-profits will crowd along Cherry Street selling handmade gifts and items designed to make a little money to help them continue their good work. Stores will be open throughout the downtown with their best, most interesting, most unusual and finest wares on display.
Somewhere in the area we'll have a big, gorgeous Community Christmas Tree, surrounded by huge gift boxes. It's a perfect setting for a family photo, so be sure to bring your camera. We'll have caroling, maybe even a band, some speakers, crowds of people and late in the evening the Live Manger Scene may stroll through - I've even seen Mrs. Santa Claus. When it's over - the people of Monticello and Jefferson County can hardly wait for Christmas.

Bethlehem in Monticello December 1st and 2nd, 2017
Bethlehem in Monticello will be presented on December 1st and 2nd from 7:00 PM to 8:30 PM.  The pageant will take place on South Water Street behind the Little Angels Preschool and across from the Old Jefferson County High School.  The pageant depicts scenes from the birth of Christ with realistic sites, actors in authentic costumes and live animals, including two camels (Jeremiah and Amazing Grace), a burro, sheep, goats and chickens. In contrast to all the celebrations of the season, this is a quiet meditative walk through the ancient city of Jesus' birth - a Christmas gift to the community of Monticello and all of Florida.  Please call the church office 850-997-5545 if you have questions or can help. Or you may call Billie McClellan 850-997-4741.

Christmas Tour of Homes
By: Monticello Area Historic Preservation Association, Inc.
A self-directed tour of family homes decorated for the Christmas Holidays

December 9, 2017 
12:00 – 6:00 PM

Refreshments, tickets, information, maps, and rest rooms at Monticello Woman’s Club, 975 E. Pearl Street
Tickets #15 

  1.  1872 Denham House, 555 W. Palmer Mill Road
  2.  1880 Daffodale House, 620 W. Washington Street
  3.  Jefferson Arts, 575 W. Washington Street
  4.  Monticello Opera House, 165 W. Washington Street
  5.  1831 Woman’s Club, 985 E. Pearl Street
  6.  Elizabeth’s Cottage 1020 E. Pearl Street
  7.  1910 Simpson House 1115 E. Pearl Street
  8.  1928 Simpson House, 1235 E. Pearl Street
  9.  1890 Girardeau House 950-E. Washington Street