Latest Past Events

It’s a Wrap!

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

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 […]

33rd Annual Carols in the Park

Central Park Downtown Winter Haven Winter Haven

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 […]

Shop Small Saturday

Historic Downtown Winter Haven Winter Haven

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 […]