Top Holiday Events in Winter Haven 2026

What Are the Best Holiday Events and Things to Do in Winter Haven in 2026?

Winter Haven, Florida, offers several ways to enjoy the holiday season, from Christmas Bricktacular at LEGOLAND® Florida Resort to downtown holiday lights, local markets, community parades and outdoor activities. Families can combine seasonal entertainment with shopping, dining, lakefront outings and attractions throughout Winter Haven and nearby Polk County.

Some of the key events to consider in 2026 include LEGOLAND® Christmas Bricktacular, the Haven Holiday Market on November 21, the Havendale Christmas Parade on December 4 and seasonal celebrations in downtown Winter Haven. Event dates and activities vary, so check the latest schedules before planning your visit.

Winter Haven Holiday Events in 2026 at a Glance

1. Celebrate Christmas at LEGOLAND® Florida Resort

Location: LEGOLAND® Florida Resort, Winter Haven
2026 dates: Select dates from November 21, 2026, through January 3, 2027
Admission: Included with general Theme Park admission on event dates

LEGOLAND® Christmas Bricktacular is a featured holiday experience in Winter Haven for families who want to combine seasonal entertainment with a full day of rides, attractions and LEGO® activities.

During the Christmas season, LEGOLAND® Florida Resort adds festive decorations, holiday character experiences, LEGO® building activities and seasonal entertainment to the Theme Park. The 2026 celebration also introduces new experiences for families to explore.

What's New at Christmas Bricktacular in 2026?

• Christmas Drone Show Featuring LEGO® Santa: A new festive drone show on select dates.

• Interactive Festive Light Trail: A holiday light experience featuring interactive LEGO® brick-building activities.

• Rap Battle Show: A new seasonal entertainment offering for the 2026 celebration.

• LEGO® Christmas Tree: See the Resort's towering 30-foot LEGO® Christmas Tree.

• Holiday character experiences: Look for LEGO® Santa and other festive characters during the seasonal event.

• Seasonal food and activities: Add holiday treats and LEGO® building experiences to your Theme Park day.

The drone show does not operate on every Christmas Bricktacular date, so check the entertainment schedule when selecting a visit day.

Christmas Bricktacular is included with general Theme Park admission on event dates. Eligible Annual Passholders can also attend, subject to pass terms and applicable blockout dates.

For families visiting Winter Haven during November, December or early January, Christmas Bricktacular is a way to build holiday entertainment into a larger day of family activities.

Learn more about LEGOLAND® Christmas Bricktacular.

2. Shop Local at the Haven Holiday Market

Date: November 21, 2026
Location: Central Park, Downtown Winter Haven
Admission: Free

The Haven Holiday Market is a community shopping event where visitors can browse local vendors and find gifts, crafts and seasonal products. The 2026 market is scheduled to feature more than 250 vendors, with offerings that include arts and crafts, holiday décor, vintage items, food, local authors, food trucks and live music.

The market is a good option for visitors who want to support local businesses while enjoying a seasonal outing in downtown Winter Haven.

Families can browse vendor booths, look for handmade gifts and take a break for food and entertainment. Because the market is held in Central Park, visitors can also explore nearby downtown shops and restaurants.

Best for: Holiday shopping, local crafts, food and a family-friendly community event.

3. Watch the Havendale Christmas Parade

Date: December 4, 2026
Time: 7 p.m. to 9 p.m.
Location: Havendale Boulevard, Winter Haven and Auburndale

The Havendale Christmas Parade is a community tradition that brings together Winter Haven and neighboring Auburndale for an evening of holiday celebration.

The parade is scheduled to travel approximately 3.1 miles along Havendale Boulevard, starting near 14th Street in Winter Haven and continuing west toward Auburndale. Local businesses, schools, community groups, marching bands and other participants help bring the route to life with decorated entries.

For families who enjoy holiday parades, it is an opportunity to see local organizations take part in a seasonal event without planning a full day at a theme park.

Best for: Families, community celebrations and an evening holiday outing.

Check the current event information before traveling in case route details or timings change.

4. Explore Downtown Winter Haven During the Holidays

Downtown Winter Haven is worth adding to a holiday itinerary, especially for visitors who want to explore local businesses, grab a meal or enjoy a community event between larger attractions.

The downtown area offers restaurants, independent shops, public spaces and seasonal programming. It can also serve as a starting point for a relaxed afternoon or evening in the city.

Look for Starlight Nights

Starlight Nights is a seasonal holiday lighting tradition associated with historic Downtown Winter Haven. Past celebrations have featured illuminated streets, decorated storefronts and photo opportunities throughout the downtown area.

For 2026, confirm the current lighting dates and hours before visiting. If the displays are operating during your trip, consider combining an evening walk with dinner or shopping downtown.

Attend Winter Haven First Friday

Winter Haven First Friday is a recurring downtown event featuring local shopping, dining, live music and a community car show.

The December 2026 event is scheduled for December 4, from 5 p.m. to 8 p.m. Visitors can explore participating businesses and restaurants before or after other seasonal activities, while checking event details for the latest entertainment and offers.

Best for: Visitors looking for local shops, restaurants, live entertainment and a community atmosphere.

5. Visit the Winter Haven Farmers Market

The Winter Haven Farmers Market offers a different way to explore the city during the holiday season. The market features local food vendors, fresh produce, baked goods, crafts, plants and artisan products, along with live music.

The market is held on Saturday mornings along Magnolia Avenue in downtown Winter Haven. Scheduled December 2026 dates include December 5, 12, 19 and 26.

Visitors can browse locally made products, pick up food and explore the surrounding downtown area. It can be a useful stop for families who want a relaxed morning activity before heading to another attraction.

Best for: Local shopping, food, handmade products and a casual outdoor outing.

Check the current market calendar before visiting, as vendors and operating details can vary.

6. See the Cypress Gardens Water Ski Show

Location: Martin Luther King Jr. Park on Lake Silver, Winter Haven
Scheduled December date: December 19, 2026
Time: 4 p.m. to 6 p.m.
Admission: Free

Winter Haven has a long connection to water skiing, and the Cypress Gardens Water Ski Team continues that tradition with public performances on Lake Silver.

The show features water-ski performers and is an option for visitors who want to experience something connected to Winter Haven's local history rather than another holiday shopping or theme park activity.

Bring a blanket or lawn chairs if permitted by the current event guidance, and check the team's schedule before heading to the park. Performances are weather-dependent and additional dates may be announced.

Best for: Outdoor entertainment, families and visitors interested in Winter Haven's water-ski heritage.

7. Enjoy Winter Haven's Chain of Lakes

Winter Haven is known for its Chain of Lakes, which offers opportunities to enjoy the area's waterways and outdoor scenery.

Depending on the season, weather and availability, visitors can look into guided boat cruises, lakefront parks and other water-based activities. These experiences can provide a slower-paced break from holiday shopping and seasonal entertainment.

Consider a Scenic Boat Cruise

A guided cruise is one way to experience the Chain of Lakes and see parts of Winter Haven from the water. Check the current cruise schedule, departure location, duration and reservation requirements before booking.

Spend Time at a Lakefront Park

Winter Haven's public parks offer space for walking, relaxing and enjoying the outdoors. Martin Luther King Jr. Park is also the setting for the Cypress Gardens Water Ski Show on scheduled dates.

If your itinerary includes a full day at LEGOLAND® Florida Resort, a separate lakefront outing may work better on another day, depending on your group's energy and schedule.

Best for: Outdoor activities, scenic views and visitors looking to experience more of Winter Haven beyond its attractions.

8. Explore Local Restaurants and Shops

A holiday visit to Winter Haven can include more than scheduled events. Downtown restaurants and local businesses offer opportunities to explore the city at your own pace.

Consider planning a meal around a downtown event, browsing independent shops or stopping for a coffee between activities. Visitors attending the Haven Holiday Market or Winter Haven First Friday can build extra time into their plans to explore nearby businesses.

For families staying in Winter Haven for more than one day, local dining and shopping can also provide an easy way to break up a busy attraction itinerary.

Best for: Visitors who want to experience local businesses and enjoy a flexible outing.

9. Add a Nearby Polk County Attraction to Your Trip

If you're spending several days in Winter Haven, consider adding another attraction in nearby Polk County. The surrounding area offers gardens, historic destinations and outdoor experiences that can complement a day of family entertainment.

Bok Tower Gardens in Lake Wales

Bok Tower Gardens is in nearby Lake Wales and offers gardens, natural scenery and seasonal programming. It is a separate outing from Winter Haven itself, so allow time for travel and check the current event calendar before visiting during the holidays.

Best for: Visitors interested in gardens, outdoor scenery and a quieter activity.

When planning a trip that includes multiple Polk County destinations, check the driving distance between each stop and avoid assuming that all attractions are within walking distance of one another.

10. Plan a Family Day in Winter Haven

Winter Haven's holiday activities can be combined in different ways depending on how much time you have and what your family enjoys.

Example: A Winter Haven Holiday Weekend

Day 1: Theme park and holiday entertainment

Spend the day at LEGOLAND® Florida Resort during Christmas Bricktacular. Check the event schedule for the holiday activities and shows available on your selected date.

Day 2: Local events and downtown exploration

Start with a local market if it is operating during your visit. Explore downtown shops and restaurants, then consider a community event or outdoor activity based on the day's schedule.

Evening option: If seasonal lighting displays are operating during your stay, plan a downtown visit after dinner. Confirm the 2026 schedule before building the evening around a particular display.

This flexible approach leaves room for travel time, meals and breaks while helping you experience more of Winter Haven.

Tips for Planning Holiday Activities in Winter Haven

Confirm Dates Before You Go

Some holiday events operate on a single date, while others run on selected days throughout November, December and early January. Confirm the latest schedule before purchasing tickets or traveling.

Check Admission and Reservation Requirements

Community markets and parades may be free to attend, while attractions and special experiences may require admission or advance reservations. Review the arrangements for each activity.

Plan Around Travel Time

Winter Haven's attractions, downtown district, lakes and nearby Polk County destinations are spread across the area. Check travel times and parking options before planning several stops in one day.

Consider the Ages and Interests of Your Group

A theme park day may be a good fit for families who want rides and structured entertainment. Markets, lakefront parks and downtown outings offer more flexible options for visitors who prefer shorter activities.

Check Weather and Outdoor Conditions

Markets, parades, boat cruises and water-ski shows may be affected by weather. Review event updates before leaving and have an alternative activity in mind if an outdoor event is postponed.

Plan Your Winter Haven Holiday Visit

Winter Haven offers more than a single holiday attraction. Families and visitors can combine seasonal entertainment at LEGOLAND® Florida Resort with local markets, community celebrations, downtown dining, lakefront activities and other experiences throughout Polk County.

Start by choosing events that match your travel dates, then leave time to explore the city between scheduled activities. For families planning a holiday visit, LEGOLAND® Christmas Bricktacular adds LEGO® building, seasonal entertainment and festive displays to a Winter Haven itinerary.

Check current event schedules before visiting, especially for seasonal lighting, outdoor performances and activities that operate on selected dates.