Good morning, Greater Winter Haven.

This is Winter Haven Wake — giving you all of the fun, local events to take your visiting family to…because hosting family is easier when you can send them somewhere else.

In today’s Winter Haven Wake:

Let’s go ⬇️

— Logan Byrd and Mike Romaine

Before Winter Haven had a downtown, it had Lake Howard.

In the late 1800s and early 1900s, settlers were drawn to the lake for one simple reason. It offered fresh water, transportation, and a natural gathering place in an otherwise undeveloped landscape. Homes, businesses, and civic buildings began clustering around its shoreline, slowly forming what would become the heart of Winter Haven.

As the city grew, Lake Howard became more than scenery. It anchored early commerce, hosted community events, and served as a launching point for boat travel once canals began linking nearby lakes.

When the first canal connecting Lake Howard to Lake Cannon was completed in 1915, the lake officially became the gateway to what we now know as the Chain of Lakes.

By the 1920s and 1930s, Lake Howard was the city’s social center. Residents gathered along the water for picnics, celebrations, and evening strolls. Downtown storefronts, hotels, and civic buildings rose nearby, all oriented toward the lake. If something important was happening in Winter Haven, chances are it happened near Lake Howard.

Even as the city expanded outward, Lake Howard remained its focal point. Roads curved around it. Parks were built along its edges. And downtown continued to grow with the lake as its backdrop.

If you’ve ever driven through Auburndale during Halloween, you might recognize the house on Patterson Drive that goes all-out with animatronics each year.

What many people don’t know is that the same home has been putting just as much care into a Christmas display … and this year, it’s being shared more intentionally with the public.

The display features a mix of inflatables, older decorations with a vintage feel, and projected holiday clips. Unlike the Halloween setup, which is a walk-through experience, the Christmas version is designed to be enjoyed as a drive-by or casual stop.

The Holiday House will be lit up every evening through New Year’s, giving families plenty of time to check it out as part of their seasonal routines.

🐱 Link is an orange tabby adult male Domestic Shorthair with a calm, gentle presence and a sweet, thoughtful gaze. Neutered and easygoing, he’s the kind of cat who’s content to lounge nearby and quietly keep you company.

New to the shelter as of December 15, Link is ready to settle into a cozy home where he can relax and feel safe.

ADOPT LINK HERE

🐶 Max is a black and white adult male Labrador Retriever mix with a joyful smile and a whole lot of love to give. This neutered good boy has been at the shelter since November 27 and is always happy to greet you with a wagging tail and bright eyes.

Max would thrive in a home where he can enjoy daily walks, playtime, and plenty of affection from his people.

ADOPT MAX HERE

Check the event links for additional information.

TODAY Grove Roots Run Club | Thursday, December 11th | 6:30PM (FREE)
Location: Grove Roots Brewing
Description: A great way to kickoff the weekend! Runners and walkers are welcome- route options include 1 mile or 5K.

Santa’s Run Fest | Saturday, December 20th | 7AM ($10+)
Location: Winter Haven Chamber of Commerce
Description: The Winter Haven Optimist Club’s Santa’s Run Fest invites runners to choose a 15K, 10K, or 5K, with Kid Dashes available for children. Set in scenic Winter Haven, the race features an out-and-back course on the Chain of Lakes Trail with gentle elevation changes suitable for all levels. Event Info

Fitness at the Port | Saturday, December 20th | 9AM - 11AM ($15)
Location: Port 27
Description: A full morning of fun and fitness at Port 27! Meditation and Rev/Flow classes happen simultaneously from 9am-10am, then, the fun continues with Yoga from 10am-11am. Each class is $15/person. Event Info

A Charlie Brown Ski Show | Saturday, December 20th | 3:15PM (FREE)
Location: Lake Silver- MLK Park
Description: Bring the whole family (pets included!) and a chair or blanket to see Cypress Gardens Ski Team’s final show of the year- A Charlie Brown Ski Show! Pre-show begins at 3:15pm with the main show at 4pm. Shows are always free, but donations are welcome. Event Info

TONIGHT Starlight Cookie Stroll | Thursday, December 18th | 5:30PM - 8:30PM (FREE)
Location: Downtown Winter Haven
Description: Enjoy festive lights and decorated storefronts, vote for your favorite People’s Choice window display, and stroll between cookie stops at participating businesses enjoying Winter Haven’s small town holiday charm. Pick up your event map at the Main Street Winter Haven office from 5:30–7:30 PM and you’ll be entered for a chance to win a $100 Visa gift card. Event Info

TONIGHT Santa’s Sweet Shack | Thursday, December 18th | 4:30PM - 6PM (FREE)
Location: Auburndale Library
Description: Bring the family to Auburndale Public Library for this month’s festive family night- Santa’s Sweet Shack! Enjoy crafts, games, and- of course- sweets! Event Info

Winter Spectacular | Friday, December 19th | 6PM - 9PM (FREE)
Location: Grove Roots Brewing
Description: Don’t miss GRB’s Winter Wonderland! Complete with snow machines, Christmas lights, arts & crafts, three food trucks, cookie decorating, new GRB beers, and a visit from Mr. Claus it’s got everything for a wonderful Winter Friday night! Event Info

Holiday “Drive-in” | Friday, December 20th | 2PM - 4:30PM (FREE)
Location: Winter Haven Library
Description: Ages 17 & under and their families are invite to design their own cardboard box car and enjoy a drive-in holiday movie! How the Grinch Stole Christmas (G) will begin at 3pm and Rudolph the Red Nose Reindeer (G) will begin at 3:30pm. Bring Your Own Box encouraged- supplies are limited. Event Info

Christmas Wreath Making | Saturday, December 20th | 11AM - CLOSE ($42+)
Location: Port 27
Description: Create a custom holiday wreath with beautiful florals and greenery from Amor Flower Truck. Open 11am - Close while supplies last. Event Info

🎅 Santa Con (21+) | Saturday, December 20th | 6PM - 8PM ($10+)
Location: Downtown Winter Haven
Description: Dress in your holiday best for a festive night of sipping and strolling through downtown Winter Haven. Check in at Grove Roots Brewing between 6:00 and 7:30 PM to receive your SantaCon button and wristband, which unlock exclusive food and drink specials at more than a dozen participating locations. For every ticket purchased, $2 is donated to Operation Outreach with the Winter Haven Public Safety Department, helping provide bikes and skateboards for local kids. Must be 21+ to participate; valid ID required at check-in. Event Info & Tickets

Pajama Jam | Wednesday, December 24th | 12PM - 7PM (FREE)
Location: Grove Roots Brewing
Description: Grab your coziest holiday PJs and enjoy GRB’s annual Pajama Jam! Event Info

Winter Haven Farmers Market | Saturday, December 20th | 9AM - 1PM (FREE)
Location: NE Corner of 3rd Street and Ave C SW
Description: Fresh produce, local honey, handmade crafts, and local vendors.

Winter Haven Saturday Market | Saturday, December 20th | 9AM - 3PM (FREE)
Location: Central Park- Downtown Winter Haven
Description: A free, family- and pet-friendly market featuring arts, crafts, jewelry, food trucks, live music, and more.

Paradise Market | Sunday, December 21st | 9AM - 1PM (FREE)
Location: Camp Margaritaville Auburndale
Description: This indoor market features over 60 vendors offering baked goods, artwork, home décor, boutique clothing, and more. Open to the public and resort guests. Event Info

Live Music Christmas Eve Eve Party | Tuesday, December 23rd | 6PM (FREE)
Location: Grove Roots Brewing
Description: Get ready for the big day with GRB’s 9th annual Christmas Eve Eve Party featuring Winter Haven’s own Hunter, Sarah-Claire, & Squire Smith! You’re not going to want to miss this festive “Smith Family Christmas Special”- concert 6:30pm-9:30pm. Event Info

Theatre FINAL WEEK Annie | Various Dates | 7:30PM ($39)
Location: Winter Haven Theatre
Description: Based on the popular comic strip by Harold Gray, Annie has become a worldwide phenomenon and was the winner of seven Tony Awards, including Best Musical. The beloved book and score by Tony Award winners, Thomas Meehan, Charles Strouse and Martin Charnin, features some of the greatest musical theatre hits ever written, including “Tomorrow.” Event Info & Tickets

Theatre FINAL WEEK Plaid Tidings | Various Dates | 7PM ($39)
Location: Theatre Winter Haven- SecondStage
Description: Forever Plaid: Plaid Tidings brings back the beloved quartet for a harmony-filled holiday special packed with “Plaid-erized” Christmas classics, nostalgic humor, and audience-favorite musical moments. This lighthearted, heavenly-inspired show delivers festive fun and timeless charm; additional showtimes playing from now until Sunday, December 21st. Event Info & Tickets

Noel & New Beginnings Gala | Saturday, December 20th | 6PM ($75+)
Location: The Barn on Heartland Farm
Description: This elegant holiday fundraising evening benefits the Women’s Resource Center of Florida and features dinner, music, silent and live auctions, and inspiring stories of transformation. Proceeds support programs that empower low-income individuals and families in Polk County through emergency assistance, housing and utility support, food and hygiene services, and workforce and financial literacy programs—helping provide stability, hope, and brighter futures. Event Info & Tickets

Thanks for reading Winter Haven Wake today.

Forward this to someone who still hasn’t bought a single present.

- Logan and Mike

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