Annual Events

Where the Whole Town Shows Up

These are the Chamber's signature annual traditions — events that have shaped Chiefland's community calendar for decades and welcome visitors from across the state.

Coming Up

Upcoming events

Saturday, December 12, 2026 at 8:00 AM

Rudolph Fun Run 5K

Trail Head Park, Chiefland

A festive 5K run/walk starting at Trail Head Park, across the street from the Historic Train Depot. Registration opens at 7:00 a.m. and the run starts at 8:00 a.m. $30 in advance, $35 on race day, and children under 8 run free — costumes encouraged. All proceeds support the Chamber and its programs.

Saturday, December 12, 2026 at 10:00 AM

Chiefland Christmas Festival & Lighted Parade

Trail Head Park, 23 SE 2nd Ave, Chiefland

A full day at Trail Head Park from 10:00 a.m. to 6:00 p.m. — live entertainment, vendors, food, games, pony rides, and visits from Santa, Cindy Lou Who, and the Grinch — capped by the lighted parade, which steps off promptly at 6:00 p.m. (staging begins at 5:00). This year's theme is "Star Spangled Christmas," celebrating America's 250th birthday. Parade entries are due December 1; vendor applications are due two weeks before the festival (November 28).

Mark Your Calendar

Signature annual events

From a summer festival with 70-year roots to a festive December weekend, every event below is a free or low-cost way to experience the best of Chiefland.

Watermelon Festival crowds and fresh watermelon
First Saturday in June

Watermelon Festival

One of Chiefland's most beloved traditions, the Watermelon Festival has been running every summer since 1954 — when local farmers donated their last watermelons to celebrate the completion of new city streets. Today, farmers still donate watermelons served ice cold to all visitors.

Highlights include arts and crafts exhibits from across Florida and neighboring states, a watermelon seed-spitting contest, the watermelon parade, auction, weighing contest, and the crowning of the Watermelon Queen. Coordinated by the Chiefland Women's Club, this annual tradition draws thousands from across the state.

Chiefland Christmas Festival downtown
Each December

Christmas Festival & Parade

Chiefland's biggest winter tradition brings the whole community downtown. The festival runs 10 a.m.–6 p.m. with food, crafts, vendors, pony rides, inflatables, a rock wall, and live entertainment. At 6 p.m., the street lights up with the beloved lighted Christmas Parade.

Free admission. A great day out for the entire family — and a chance to shop local, taste great food, and feel the spirit of a Chiefland Christmas.

Enter the parade

Runners at the start of the Rudolph Fun Run 5K
Each December · Trail Head Park

Rudolph Fun Run 5K

A festive 5K run/walk from Trail Head Park held each December during Christmas Festival weekend. Registration opens at 7 a.m. and the race starts at 8 a.m. Costumes are enthusiastically encouraged — the more holiday cheer, the better.

Entry fees: $30 advance / $35 day-of. Children under 8 run free. Proceeds support Chamber programs and community initiatives throughout the year.

Register online

Chamber ribbon cutting and awards ceremony
Each Spring

Annual Awards Banquet

Each spring, the Chamber gathers to recognize the individuals and organizations who made an extraordinary difference in our community over the past year. Awards are presented for:

  • Citizen of the Year
  • Business of the Year
  • Law Enforcement of the Year

Know someone who deserves recognition? Nominations are open to all community members.

Nominate someone

Chamber members networking at a monthly luncheon
Monthly · Members Only

Monthly Member Luncheons

Every month, Chamber members gather for a networking luncheon — a relaxed setting to make connections, share referrals, hear from local leaders, and strengthen the business community that makes Chiefland run.

Luncheon tickets are included with every membership level, making them one of the most tangible day-one benefits of joining the Chamber. Whether you're a longtime member or brand new to the area, these monthly gatherings are where relationships are built.

Become a member

Need this year's exact dates?

Event dates and times are confirmed each year. For the current schedule, call the Chamber or stop by the Welcome Center in the Historic Train Depot — we'll have the latest information on hand.

Call 352-493-1849Contact us