✨ Worry Free Weekend | November 21–23, 2025 ✨

The weekend brings festive energy, outdoor glow, local markets, and plenty of opportunities to explore under the open sky. Here’s a full guide to make it feel worry-free and full of fun.

🎉 Friday, November 21

💃 Fútbol & Fiesta Weekend Kick-Off – BOXi Park
📍 BOXi Park (Orlando)
🕔 Evening (starts around 5 PM-ish)
Enjoy live entertainment, themed food + drink specials, and that lively, community-festival feel under the sky.

🛼 Free Roller Skate Night – Barber Park
📍 Barber Park, Orlando
🕠 5:30 PM – 9:00 PM
Bring your skates (or borrow some)—it’s a free skate night with music, DJ, games, and a fun throwback vibe for all ages.

🎨 Gallery or Art Stroll

  • Explore local art galleries or public art displays downtown or in a walkable arts district. Great way to soak in the evening with creativity and good company.

🌲 Evening Trail Walk

  • Take advantage of parks like Cross Seminole Trail or Seminole Wekiva Trail for a peaceful walk under the early twilight. Bring a water bottle + comfy shoes.

🌞 Saturday, November 22

🌾 Longwood Arts & Crafts Festival
📍 Longwood Historic District
🕘 9:00 AM – 4:00 PM
Browse over 200 artist booths — jewelry, décor, handmade goods — while enjoying local vendors and outdoor charm. A perfect local arts outing.

🎄 Festival of Trees – Orlando Museum of Art
📍 Orlando Museum of Art
🕙 10:00 AM – 5:00 PM
Immerse yourself in the holiday spirit with beautifully decorated trees, wreaths, gingerbread creations, live entertainment, and a holiday boutique.

🌌 Asian Lantern Festival: Into the Wild – Central Florida Zoo
📍 Central Florida Zoo & Botanical Gardens
🕕 6:00 PM – 10:00 PM
Wander through glowing lanterns, handcrafted scenes, and immersive light art in a peaceful night-walk experience.

🚶 Nature Walk or Trail Time
🕚 Late morning / early afternoon
Explore shady trails like Green Springs Park or Little Econ Greenway for nature time, fresh air, and relaxation.

🌼 Sunday, November 23

🛍 Sunday Outdoor Market – Central Florida Fairgrounds
🕖 7:00 AM – 3:00 PM
An open-air market with local vendors, crafts, food, and great people-watching. Perfect start to a mellow Sunday.

🥕 Maitland Farmers’ Market
📍 Maitland City Centre
🕘 9:00 AM – 1:00 PM
Shop fresh produce, baked goods, handmade items — all while enjoying a lakeside park atmosphere.

🎨 Fall Festival of the Arts – DeLand
📍 Woodland Boulevard, DeLand
🕙 10:00 AM – 4:00 PM
Over 170 national artists display their work — painting, sculpture, photography — plus food, live music, and outdoor art browsing.

🌿 Trail & Picnic Time
🕒 Afternoon
Wrap up the weekend with a relaxing walk or bike ride on Cross Seminole Trail or a picnic at Gemini Springs Park or Green Springs Park.

💡 Trail & Outdoor Favorites (Anytime This Weekend)

  • Cross Seminole Trail — 23 mi of paved walking and biking in Seminole County. Wikipedia

  • Seminole Wekiva Trail — a 14-mile paved multi-use trail, great for walkers, cyclists, and families. Wikipedia

  • Mennello Museum of American Art — art + quiet gardens for strolling and reflection. Wikipedia

✅ Pro Tips to Make the Weekend Smooth

  • Bring cash & tote bags for market and festival vendors.

  • Wear comfy shoes — with so much walking, your feet will thank you.

  • Use a small flashlight or phone light for evening trail walks.

  • Pack water and light snacks — outdoor exploring builds up appetite!

  • Mix it up: try one “go out” activity + one relaxing outdoor moment each day.

This weekend, fill your days with glowing lanterns, creative art, local makers, and trail time — all tuned to your pace and style. Enjoy every moment of your Worry Free Weekend! 💚

And if you’re looking for things to do year round, check out our other blog!

Free and Budget Friendly Things To Do in Central Florida