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Downtown Winter Haven and the Chain of Lakes from the air above The Jade

A Winter Haven Guide

Downtown Winter Haven, block by block.

Downtown Winter Haven is a few walkable blocks of brick storefronts around Central Park. It has a brewery, a century-old theater, a Saturday market, and events through the year. This guide covers where to eat and drink, what is on, and living nearby.

The lay of the land.

Downtown Winter Haven is small and walkable, and most of it sits within a few blocks of Central Park. Shops and restaurants line Central Avenue, and Fountain Walk has its fountains. The Chain of Lakes Trail runs along the western edge past the K9 Courtyard dog park, and the lakes sit at the ends of the east-west streets.

Fountains along Fountain Walk in downtown Winter Haven
Fountain Walk, downtown Winter Haven · photo Ultrahip, CC BY-SA 3.0

Where to eat and drink.

Beyond the short list below, downtown also has Thai, sushi, southern barbecue and bakeries. Main Street keeps the full directory (opens in a new tab).

  • Grove Roots BrewingThe hometown brewery, downtown
  • Union TaproomCraft pours across from Central Park
  • Barrel 239A whiskey bar with hundreds of bottles and a turf patio
  • Arabellas RistoranteItalian in Times Square, the dressed-up night out
  • Richard's Fine CoffeesThe downtown coffee counter
  • Saturday farmers marketProduce, makers, and music, every Saturday morning

A year on Central Avenue

Downtown after dark.

The Ritz Theatre has held its corner for about a century and still runs live shows, and Theatre Winter Haven produces a full season of its own. Main Street Winter Haven (opens in a new tab) runs the rest of the calendar. Dates move a little each year, and its site and the city’s calendar post the current ones.

The Ritz Theatre marquee at night with car light trails along Central Avenue
The Ritz Theatre · photo Andrew Heneen, CC BY 4.0
  • First FridayDowntown, the first Friday evening of each month
  • OktoberfestCentral Park, each fall
  • Holidays on CentralCentral Park, each December

Live a walk away from all of it.

The Jade Apartments is about a 15 minute walk from downtown, close enough to walk to the Saturday market. What a lease costs is published in full, and the floor plans show the three homes. see the neighborhood (Distances and travel times are approximate, under typical conditions.)

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