Starlight Nights Downtown

Historic Downtown Winter Haven Winter Haven, Florida

 Main Street Winter Haven & The City of Winter Haven are thrilled to announce Downtown's Winter Haven's newest Holiday tradition - 
Starlight Nights! For six weeks, Downtown Winter Haven will be dazzling with lights as 
we ring in the season of Holiday cheer and togetherness. Dine, shop, and enjoy a beautiful evening stroll with fun […]

Shop Small Business Saturday 2020

Historic Downtown Winter Haven Winter Haven, Florida

Come out and support your local small businesses in Downtown Winter Haven on November 28th! Be sure to visit each of the participating businesses and get an early start on holiday shopping! Shop Small Scavenger Hunt: 1. Pick up your Shop Small Scavenger Hunt map at any of the participating businesses, or download the image […]

Bark in the Park 2021

Central Park Downtown Winter Haven Winter Haven, FL

It’s a dog day in Downtown Winter Haven! Spend your FREE Friday night shopping pet vendors, enjoying a cold beverage, and enjoying time with your favorite four-legged friends. This year's event will be held in Central and South Central Park Downtown - with favorites like the police K9 demonstration and our Annual Weiner Dog Race! […]

Treasure Hunt Downtown 2021

Chamber of Commerce 401 Ave B NW, Winter Haven, FL

Main Street Winter Haven, in partnership with our Downtown businesses, presents our Annual FREE Treasure Hunt Downtown. Children under the age of 12 will search for LEGO® Minifigures in the participating locations Downtown! Pick up your FREE treasure map from the Chamber of Commerce Breezeway between 11AM-1PM. Participating downtown businesses will hide a LEGO® Minifigure […]

Oktoberfest Downtown 2021

Central Park Downtown Winter Haven Winter Haven, FL

Oktoberfest is a celebration of Bavarian traditions, food, and, most importantly, BEER! 🍺 Central and South Central Park in Downtown Winter Haven will be transformed into a German biergarten, as attendees are invited to sample over 40 craft, local and international beers. Tasting Tickets are $25 and available using the link below: OKTOBERFEST TICKETS HERE […]

Carols in the Park 2021

Central Park Downtown Winter Haven Winter Haven, FL

32nd Annual Carols in the Park presented by Citizens Bank and Trust December 4, 2021 10AM - 6PM Main Street Winter Haven is thrilled to announce our 32nd Annual Carols in the Park presented by Citizens Bank and Trust! For over thirty years, artisans, specialty food vendors, and local choral groups have gathered in Downtown […]

Bark in the Park 2022

Central Park Downtown Winter Haven Winter Haven, FL

It’s a dog day in Downtown Winter Haven! Spend your FREE Friday night shopping pet vendors, enjoying a cold beverage, and enjoying time with your favorite four-legged friends. This year's event will be held in Central and South Central Park Downtown - with favorites like the police K9 demonstration and our Annual Weiner Dog Race! […]

International Food & Drink Street Festival

Central Avenue Downtown Winter Haven

Calling all foodies!  You won’t want to miss the International Food and Drink Street Festival on October 20! Take a taste tour through Downtown Winter Haven and experience food and paired drinks from around the world. We will close down Central Avenue and 3rd Street for this International celebration in the street! This event is […]

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

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 […]