Monticello Florida’s Annual Bike Fest

April 1, 2017.

This competition is routed around and through the unsurpassed beauty of rural Jefferson County, the heart of the Red Hills. Follow the curves of Gamble Road, surge along the Old Spanish Trail, idle past Lake Miccosuki or coast down the gentle slopes of Plantation Way.

Whether you ride for fun, feel a little competitive or are determined to win a trophy – this is it. You don’t want to miss the biggest happening scheduled for this Spring – APRIL  2017 — in North Florida.  

If you don’t compete, come and enjoy the race – watch cyclist curve along the round-about in front of our famous Historic Courthouse. Meet and congratulate race winners.

Wander along historic streets lined with amazing nineteenth century houses. Eat in great restaurants. Visit stores filled with a wonderful variety of furniture, antiques, collectibles and art.

Meet great people you will never forget. There’s nothing formal about it, just say you are enjoying the town and Monticello people will jump at the chance to talk about the hometown they love.

The Monticello Bike Fest is handled by the Monticello/Jefferson County Chamber of Commerce at info@monticellojeffersonfl.com or phone Katrina at 850-997-5552.



DUELS in Monticello Florida

Courthouse at EveningI’ve read of historic duels between several old families in Jefferson County. The stories always include the participants moving the actual event north about five miles to the “no-man’s’land” at the Florida-Georgia border. The story always further explains that the actual border had not been exactly pinned down at the time, so neither locale’s sheriff felt he had jurisdiction. Therefore the duelists did not worry that dueling had been declared illegal in both states. They were ready to fight!duel

It’s different now, in 2017 we still duel, oh yes, but we handle these contests in a legal way. Here are the rules: All antagonists must register with the Monticello/Jefferson County Chamber of Commerce. It’s located on West Washington Street. Then they must gather at the dueling grounds on the appointed day – that’s the Old Apron Factory on south Jefferson Street – (you’ll see a Simpson’s Nursery sign) Don’t pay any attention, it’s still the appointed LEGAL dueling grounds.

Most of the historical antagonists tried to keep their duels a secret according to Shofner, but nowadays every one of them blatantly advertises his fight. They ask people to come and watch! It really is a DO NOT MISS event for the whole area. We even invite people from north of the Georgia border.

Located - Pearl and Jefferson

Located – Pearl and Jefferson

All the duelists will congregate in the Old Apron Factory, South Hwy 19, Monticello, Florida on February 18 @ 5:00 pm11:00 pm United States + Google Map for the Monticello Jefferson County Chamber of Commerce  Chili Challenge,  2077 S. Jefferson (South Hwy 19), Monticello, FL Set-up 3pm to 4:30pm; Judging 4:30pm to 5pm; Open to the Public 5pm to 7pm –

BUY YOUR TICKETS TODAY! Admission – Adults $8 (all you can eat) Children ages 5-12 $5; Ages 4 and under FREE! The Chaotics Dance 7:00PM to 10 PM – tickets $15.


Christmas Tour of Homes in Monticello, FL, 2016


Pearl Street in Monticello

Pearl Street in Monticello Florida

The 2016 Christmas Tour of Homes in the City of Monticello in Jefferson County Florida is on Saturday, December 10, 2016 from 12:00 to 6:00 PM. This event includes a self-directed tour of nine (9) historic venues and is presented by the Monticello Area Historic Preservation Association.

The tour costs $15.00 and you can buy tickets in advance from Monticello/Jefferson Chamber and several other venues in the town of Monticello and Southern Friends Framing and Antiques in Thomasville.

The most fun however, will be to go to the Women’s Club building at 985 East Pearl Street (Monticello’s prettiest street). They not only have tickets for the tour, they have their famous holiday cakes and if you are hungry they also offer a light meal for sale. The sponsors of this event provide a phone number if you have questions – 850-997-6552.

This tour encompasses an area of Monticello that is often overlooked except by local residents. You will see several houses that are truly beautiful as well as interesting historically and culturally.

One other thing you should look for during the tour is the magnificent Monticello Avenue of Oaks. These wonderful trees are worth the tour alone. Ask someone to direct you when you visit the Women’s Club.

The tour sponsor, Monticello Area Historic Preservation Association, works with our Women’s Club, Monticello/Jefferson Chamber, Jefferson County Tourist Development Council and Main Street of Monticello to encourage the preservation of the treasured buildings in this tiny 1827 town.

Monticello’s tree lined streets are full of small and large historic homes, many dating from before the Civil War. They are an expression of the best of our culture and we welcome your visit.

JC #1 347

JC #1 248

Located - Pearl and Jefferson

Located – Pearl and Jefferson

Monticello Christmas

by Anne Haw Holt


A Story for Santa – Anne Holt

Christmas starts this Friday evening — that’s December 2! Monticello Downtown Christmas is always the first to celebrate this beautiful season. Starting around 5:00 or 5:30 PM the streets just north of the festively decorated Courthouse will be full of families hurrying to the garden at the Wirick-Simmons House to see the lighting of the community Christmas tree and hear the choirs singing old fashioned carols.

Carolers by Anne Holt

Shoppers will be visiting the interesting displays of gifts in our town’s unusual collection of specialty shops. Children will be watching for Santa to arrive on a fire truck.
East Dogwood Street will be full of colorful booths offering everything from the Monticello Women’s Club’s fabulous “Old Fashioned Christmas Fruitcake” to handmade jewelry, books and unusual gifts.
Carolers will stroll by. You may even hear someone reading “T’was the Night Before Christmas.” Children will sit in Santa’s lap as parents take their picture. Many will pose to take a family photo in front of the Community Christmas tree—ask someone to help, you’ll make them happy.
A little later, right in front of the public library on Water Street (two blocks south of Washington St. or Rt. 90) our beautiful live nativity scene, “Bethlehem in Monticello” will open. Children will marvel when they men, women and child actors with live animals bring the real Christmas story to life.

Bethlehem in Monticello Photographs by John Hicks

Bethlehem in Monticello - photo by John Hicks



9th Annual Farm Tour

Farm Tour 2016

Farm Tour 2016

Billed as a great family weekend, the Ninth Annual Farm Tour includes visits to more than twenty farms. Happening next weekend, October 22 and 23, 2016, visitors will learn about local farms, resource organizations, small gardeners and related vendors. There are farms near you in Leon County, Gadsden County, Jefferson County, Madison or Taylor County and farther west.

Jefferson County has a surprising lot of farms on this tour. Those farms will be open and welcoming you. I know of a farm where they specialize in Tennessee Fainting Goats, (be sure to see the great dogs who protect them). You will find farms that raise large varieties of vegetables, others that specialize in just a few or even in different kinds of fruit. There’s another near Monticello that raises bees and sells honey. You will find 20 farms in all, probably more than you can visit in a weekend.

Some of these most interesting places have mazes and other entertainment for your children and grandchildren, special entertainment besides the expected animals, chicken, turkeys and equipment they will be interested in seeing. Oh – there’s even a farm near Monticello where they grind Sugar Cane another that makes Mayhaw jelly.


Booklets with a map and complete information are available in many places in Monticello, Tallahassee, Greenville, Havana and other towns—even Bonifay and Eridu.

Remember, this is a self-guided tour. Each farm on the map gives you its own contact information. Don’t bring your pets, farm animals just don’t appreciate them as much as you do. Enjoy your weekend.

Lists of Farms to Visit

Monticello’s Harvest Dinner in a Rain Storm

Dessert Table - Harvest Dinner

Friends at Dinner

                         All seats were sold out, of course.  

All the best people were there — ready for a great Saturday evening at the Harvest Dinner by the Jefferson County Historical Association. Tables  placed around the Wirick-Simmons Garden in Monticello were all full. Guests ate venison, quail, sweet potatoes, deviled eggs and more. 

Barbara presided over yummy looking cakes, from pecan to double chocolate.

Then it sprinkled a little rain.

Everyone laughed a little and continued eating and talking to their friends around the large round tables.

Then it started to rain seriously. It began to pour. The wind blew and it rained — Oh my, how it rained.

As one, members of the group grabbed their plates and rushed under the large serving tent. Instead of six people at a table they crowded in twelve or maybe more – still enjoying their food.

Others stood along the serving tables. Some held their fine china plate in one hand and their real silver fork in the other. No matter the little rain problem, the food was delicious even interesting—and the company was better.

Some might want to say the Jefferson County Historical Association’s Harvest Dinner was rained out this year. They might want to say the event was a wash out, but that’s not what happened. We had a fabulous time and will never forget the wonderful Harvest Dinner when it rained buckets for hours. The dinner where we crowded in the serving tent, enjoyed our meal, our dessert. Some even finished with a cup of coffee, and we talked.

Yes, we talked. Groups formed and re-formed we reached out to everyone. Newcomers met life-long residents. We had time—time to find out what our old and new friends were doing and how things changed in their lives. We will certainly never forget this Harvest Dinner. When it was over, we realized — we didn’t mind a little rain at all.

Friends Eating and Laughing

Friends Eating and Laughing

Laughter is the best medicine.

Laughter is the best medicine.

Watermelon Festival 2016

by Anne Haw Holt

Monticello and Jefferson County Florida will celebrate their sixty-sixth annual WatermelonHeaderWatermelon Festival beginning with beauty pageants on June 4, 2016. The pageants will be followed up with events such as a great kick-off dinner (must be counted as part of the famous, deliciously satisfying Monticello Food Trail) followed up by a Bed Race on June 10.  Yes I said…Bed Race….you don’t want to miss it. This traditional race is silly, funny and I found it absolutely delightful.DSC_0357

Have you ever thought of entering a watermelon seed spitting contest? Or have you run a race wearing watermelon Shoes? Don’t miss the Watermelon Patch, watching your friends seriously try to win one of these events is as much fun or more than participating.

In addition to all the fun events, the town will be full of interesting vendors selling everything from cotton candy and Kettle Korn to hot dogs and handmade handbags. You’ll find pottery, jewelry, wood carving, books and other works of art all along Cherry, Dogwood and Pearl Streets in front of our gorgeous historic buildings.

Most small town festivals are hokey and old fashioned, but infinitely charming. This one is also surprisingly entertaining and definitely worth attending every event. Wear comfortable shoes and plan to stay late. No one does this better than Monticello….you’ll be charmed.

Watermelon Festival Schedule

June 4th  Pageants
June 10th Kick -Off Dinner, Bed Race, and new this year – Rodeo
June 11th – Rodeo
June 16th – Woman’s Club Fashion Show
June 17th Arts & Crafts, Rotary BBQ, Street Dance, Kids Show – Tale of Peter Rabbit
June 18th Kiwanis 5K Run, FMB Breakfast, MADCo. Kids Show – Tale of Peter Rabbit,  Platform Events, Parade, Arts & Crafts and new this year Watermelon Contests in the Watermelon Patch