Wine, Chocolate and Cheese 2022

Central Avenue Downtown Winter Haven

Main Street Winter Haven hosts our annual Wine, Chocolate and Cheese event in Downtown Winter Haven! On Thursday, November 17th over 30 downtown businesses will host a wine & chocolate or a wine & cheese pairing. Your Tasting Passport will take you from business to business to sample each of the combinations! Live music on […]

Shop Small Saturday

Historic Downtown Winter Haven Winter Haven, Florida

Come out and support your local small businesses in Downtown Winter Haven on November 26th! Be sure to visit each of the participating businesses and get an early start on holiday shopping! 🎪 Welcome tent with hot coffee and maps of Downtown businesses with their Shop Small specials! 🎁 Raffle entry with every Downtown receipt […]

33rd Annual Carols in the Park

Central Park Downtown Winter Haven Winter Haven, FL, United States

Main Street Winter Haven is thrilled to announce our 33rd Annual Carols in the Park presented by Citizens Bank and Trust! For thirty three years, artisans, specialty food vendors, and local choral groups have gathered in Downtown Winter Haven’s Central Park to kick off the holiday season. This event has become a tradition for multiple […]

It’s a Wrap!

Main Street Office 254 W. Central Ave. Suite F, Winter Haven, United States

To show how much we appreciate your decision to shop Downtown, we would love to help you WRAP UP your Holiday shopping! 🎁 1. Purchase your Holiday gift at any of our Downtown Winter Haven businesses. 2. Bring the gift and receipt to our wrapping station (Main Street Winter Haven office). 3. Our volunteers will […]

Craft Beer Crawl 2023

Historic Downtown Winter Haven Winter Haven, Florida

A long time ago in a Downtown far, far away....or right here in your community! Main Street Winter Haven invites you to celebrate May the Fourth with good friends and GREAT beer! Come explore Historic Downtown Winter Haven while sampling specialty CRAFT BEERS & BITES in our participating shops and businesses! Don't forget your Star […]

Bark in the Park 2023

Central Park Downtown Winter Haven Winter Haven, FL, United States

Spend your FREE Friday night shopping pet vendors, enjoying a cold beverage, and enjoying time with your favorite four-legged friends. Bark in the Park will be held in Central and South Central Park Downtown - with favorites like the police K9 demonstration and our Annual Weiner Dog Race! 🐾 VENDOR APPLICATION HERE  

Wine, Chocolate & Cheese

Central Avenue Downtown Winter Haven

Main Street Winter Haven hosts our 9th Annual Wine, Chocolate, and Cheese event in Downtown Winter Haven, on November 3, 2023, from 5:30-8:30 PM! We invite you to explore Downtown Winter Haven while enjoying Wine, Chocolate, and Cheese. Tasting tickets include a specially designed map that outlines the participating businesses and the official tasting glass. […]

Starlight Skating – Downtown Winter Haven

Get ready to glide into the holiday spirit as an enchanting ice skating rink arrives in Downtown Winter Haven for two unforgettable days on December 2nd and 3rd! Join us for a magical experience as we transform the heart of the city into a winter wonderland, perfect for family fun, a date night, or a […]

Starlight Stroll – Downtown Winter Haven

Join us for an evening at the heart of downtown Winter Haven and partake in the Starlight Stroll! Experience the magic of the Holiday Season as the city comes alive with twinkling Christmas lights and enchanting window displays. We invite you to take a leisurely stroll through the streets adorned with breathtaking lights and Holiday […]

Sidewalk Shopping – Downtown Winter Haven

Join us for a festive day of shopping and holiday cheer in Downtown Winter Haven! On December 16th, from 10am to 2pm, Central Avenue comes alive with a sidewalk shopping experience. Businesses are spreading the holiday spirit by utilizing our newly expanded sidewalks, creating a vibrant and welcoming atmosphere for all. Explore an array of […]