December 2025 Events Around the Big Bend: Tallahassee, Havana, Monticello, Crawfordville & Thomasville, GA
Tallahassee Local Events Velinda Hittinger November 21, 2025
Tallahassee Local Events Velinda Hittinger November 21, 2025
December has a special way of bringing the Big Bend to life. Lights sparkle on old brick streets, music fills the air, and families gather to enjoy traditions that feel warm and familiar. If you’re planning to spend time around Tallahassee, Havana, Monticello, Crawfordville & Thomasville, GA this holiday season, you’ll find no shortage of festive fun. Each of these towns celebrates December in its own way, and that’s part of what makes the Big Bend such a great place to explore.
This guide gives you an easy list of real events happening across the region in December 2025. Whether you’re a local looking for something new or a visitor trying to make the most of your trip, this list keeps things simple. The goal is to help you enjoy the season without the stress of searching for events yourself. So grab a warm drink, get comfy, and let’s take a tour of everything happening this December. Read on to learn more.
December in Tallahassee always feels like the city is wrapped in a big holiday bow. Something is happening everywhere from downtown streets to local museums. If you love live music, bright lights, holiday markets, or outdoor family fun, you’re in the right place.
Date: December 6, 2025
Time: 3:00 p.m.–10:00 p.m.
Location: Downtown Tallahassee
The Winter Festival is one of Tallahassee’s favorite traditions. The whole downtown area comes alive with holiday magic. You’ll see streets lined with food trucks, local art vendors, and joyful performances. Kids love the hands-on activities, and adults enjoy the music, lights, and community feel. The holiday parade is the cherry on top, and it always brings out smiling crowds. If you want that classic holiday atmosphere, this is the event to mark on your calendar.
Date: December 6–7, 2025
Location: North Florida Fairgrounds
Market Days is one of the largest arts-and-crafts events in the Southeast. It features more than 300 vendors, so you can imagine how easy it is to get lost in all the fun. You’ll find handmade gifts, home décor, jewelry, seasonal treats, paintings, and everything in between. It’s a great place to shop for holiday presents while supporting small businesses. And honestly, who doesn’t love walking around with a cup of hot cocoa while browsing unique finds?
These Tallahassee events draw big crowds each year because they’re fun, festive, and full of that holiday spirit everyone loves.
Havana may be small, but it shines bright in December. The town is known for its antique shops, charming streets, and cozy atmosphere. When the holidays arrive, Havana becomes a beautiful place to spend time with friends and family.
Date: December 13, 2025
Time: 10:00 a.m.–4:00 p.m.
Location: Downtown Havana
This cheerful event fills the entire downtown area. You’ll find craft booths, local vendors, warm holiday foods, music, and friendly faces everywhere you go. It’s the kind of event where you can stroll slowly, take your time, and enjoy every little moment. WinterFest feels like a perfect small-town Christmas movie come to life.
Date: December 13, 2025
Time: 1:00 p.m.
Location: Downtown Havana
Now this one is truly unique. Instead of floats and huge performance trucks, locals decorate their lawnmowers and parade them through town. It’s funny, charming, and so full of personality. It’s one of those events that reminds you why small towns have the best holiday traditions. Kids love it, adults love it, and everyone ends up smiling.
Havana’s holiday events make the season feel down-to-earth and joyful. Sometimes simple celebrations are the ones you end up remembering most.
Monticello’s historic charm makes December feel magical. With its beautiful courthouse square and classic holiday decorations, it’s easy to fall in love with this small town during the holidays.
Date: December 6, 2025
Time: Evening hours
Location: Downtown Monticello
Monticello’s Christmas Light Parade is a long-standing favorite. Local groups decorate bright, colorful floats, and the community fills the sidewalks to watch them roll by. You’ll hear music, see lights flashing, and feel the joy in every direction. After the parade, you can enjoy the festive decorations around the town square. It’s an easy way to slow down and soak in the holiday spirit.
Monticello offers a peaceful seasonal atmosphere that blends history, tradition, and community. If you’re looking for a relaxed holiday outing, this is a great spot.
Crawfordville offers a nice mix of nature and community, and December brings both together in a way that feels warm and welcoming.
Date: December 6, 2025
Time: 10:00 a.m.
Location: Hudson Park, Crawfordville
This heartwarming event supports wildlife rescue and rehabilitation efforts. Families are invited to decorate native trees, meet animal ambassadors, and enjoy a cheerful day outdoors. There are also raffles, treats, and holiday activities for all ages. If you’re an animal lover or enjoy giving back during the holidays, this event is a wonderful way to do it.
Crawfordville’s holiday celebrations may be smaller, but they’re filled with real meaning. You’ll feel connected to the community and the natural world at the same time.
Just a short drive from Florida, Thomasville, GA is known for its historic charm. December lights up the town with traditions that bring people from all over the region.
Date: December 11–12, 2025
Time: 6:00 p.m.–9:00 p.m.
Location: Downtown Thomasville
This is one of the biggest and most popular holiday events in the Big Bend region. Victorian Christmas transforms downtown Thomasville into a beautiful scene from the past. You can enjoy carriage rides, listen to carolers, watch blacksmith demonstrations, taste roasted chestnuts, and walk through charming shops. The streets are filled with warm lights, music, and the sound of people laughing and enjoying the moment. It feels like stepping into a holiday postcard.
Date: December 1, 2025
Time: 6:30 p.m.
Location: Downtown Thomasville
Thomasville kicks off December with its annual parade. Expect bright lights, decorated floats, bands, dancers, and lots of holiday cheer. Families fill the sidewalks early to get a good spot, and the whole downtown glows with excitement.
Thomasville is a must-visit during December because it blends tradition with fun in a way that feels both nostalgic and exciting.
Getting the most out of your holiday adventures is easier when you plan ahead. These simple tips can help you enjoy every moment without stress.
Arrive early for parades and festivals: Popular events fill up fast, especially in small towns where parking is limited. Getting there a little early helps you find a good spot, avoid long lines, and settle in before the crowds roll in.
Check event websites or social pages for updates: Schedules can shift because of weather, road closures, or last-minute changes. A quick check before you head out saves you a lot of frustration. Most events post updates on Facebook or Instagram.
Support local shops and vendors: Holiday events are packed with small businesses selling handmade gifts, baked treats, art, jewelry, and holiday décor. Buying local not only helps the community but also makes your gift-giving more meaningful.
Carry a little cash or smaller bills: Many vendors take cards, but some still prefer cash, especially for small items like snacks, ornaments, or raffle tickets. Bringing cash helps you avoid long payment lines or card-reader delays.
Plan your parking or transportation ahead of time: For bigger events in Tallahassee or Thomasville, some streets may be blocked off. Knowing where to park or using rideshare can save you time and stress.
Bring a tote bag for shopping: With all the local vendors selling cute holiday gifts, it’s nice to have a bag to hold everything you pick up along the way.
These easy tips help you enjoy December across the Big Bend with fewer worries and more fun. After all, the holidays are meant to feel joyful and simple, just the way small-town celebrations should be.
If you have extra time while exploring Tallahassee, Havana, Monticello, Crawfordville & Thomasville, GA during these December events and want to learn more about homes in the area, I’d love to help. Whether you have real estate needs right now or you’re planning ahead for 2026, you can always reach out. As a Realtor in North Florida, I’m here to make the process easy and enjoyable. Feel free to contact me anytime if you're curious about neighborhoods, homes, or next steps.
Happy Holidays!
Always,
Velinda Hittinger, REALTOR
Armor Realty
M: (850) 545-7219
Do you have an Instagram? Let's Connect- IG @ velindahittinger_realtor
Tallahassee Local Events
Tallahassee Local Events
Tallahassee Local Events
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