Wine Chocolate and Cheese 2021

Historic Downtown Winter Haven Winter Haven, Florida

Main Street Winter Haven hosts our annual Wine, Chocolate and Cheese event in Downtown Winter Haven on November 12, 2021! On Friday, November 12th 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 […]

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 […]

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

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

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 […]