Shop Small

Come out and support your local small businesses in Downtown Winter Haven on November 24th! 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. 2. Visit as many […]

30th Annual Carols in the Park

South Central Park Downtown Winter Haven Winter Haven, Florida

Main Street Winter Haven is thrilled to announce our 30th Annual Carols in the Park presented by Citizens Bank and Trust! For thirty 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 generations, […]

31st Annual Carols in the Park

South Central Park Downtown Winter Haven Winter Haven, Florida

31st Annual Carols in the Park presented by Citizens Bank and Trust December 7, 2019 10AM - 7PM Main Street Winter Haven is thrilled to announce our 31st 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 […]

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 […]

Carols in the Park 2021

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

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 […]

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 […]