Bringing Back Main Street

It’s happening all over Florida: residents are rediscovering Main Street, preserving historic architecture, returning to walkable neighborhoods, and engaging with their neighbors. Some of our historic cities, like Mount Dora and Bradenton, have managed to preserve this small town feeling on their own, but many others are taking advantage of the concerted efforts of the Florida Main Street Communities program, affiliated with the National Trust for Historic Preservation’s Main Street America initiative.

Here are a few other small towns with a Main Street, community-oriented feel—one that cultivates a calmer, more congenial way of life.


Kissimmee is a Florida Main Street program success story. Its attractive downtown retail core is filled with two- and three-story brick buildings that now house a collection of family-owned eateries, sidewalk cafes, shopping, and retail services. What’s more, the downtown plays host to festivals and activities for residents year-round, including an annual Chili Cook-Off and Beer Festival, community-based trick-or-treating for the kids, a yearly birthday bash (Kowtown Festival), and a weekly farmers’ market, recurring every Tuesday evening from 3-7.

Winter Haven

(Pictured Above) In mid-state Winter Haven, community leaders began revitalizing their downtown using a Main Street approach way back in 1995. Thanks to a strong partnership between civic and business leaders, they’ve successfully joined forces to renovate the facades of many of the downtown retail buildings, so the structures stay true to their architectural history, helping the area feel like a cohesive neighborhood. They’ve also established downtown community activities, including an outdoor sculpture competition and a guided tour of the completed works of renowned architect Gene Leedy, a founder of the Sarasota School of Architecture and a permanent Winter Haven resident since 1954.


Bartow serves as the official seat of Polk County, one of our more rural regions, where citrus, cattle, and phosphate production underpin the economy. Established in 1851, the city maintains a small town feel, with one- and two-story buildings lining retail streets, and park benches lining brick sidewalks. Here city leaders banded together to create a vibrant downtown center with a cohesive neighborly feel and opportunities to shop, dine, and socialize. The Main Street Bartow organization coordinates events and traditions that bring residents downtown. These include a weekly farmer’s market at Fort Blount Park; Friday Fest, a monthly street party; plus an annual Science Fiction fest; Honey Bee Festival & Craft Show; and Christmas parade.


Leesburg has been a Main Street program affiliate since 1994, when members of the merchants association, the chamber of commerce, and others teamed up to revitalize the historic downtown. Together with community residents and volunteers, they’ve now successfully created a beautiful, vibrant downtown district, with activities for everyone. The partnership also hosts more than 100 special events and festivals each year, including an annual Mardi Gras Celebration, BikeFest, Fish Fry, Saturday Morning Market, and a Main Street Christmas Stroll and Parade. They add events all the time, too, including the upcoming Food Truck ‘n’ Flick Night. All this serves to create a safe, appealing town center that encourages people to know their neighbors and keeps residents and visitors coming back for more.

St. Cloud Main Street

A mere 26 miles southeast of bustling Orlando is St. Cloud, a small, historic city on the southern shore of East Lake Tohopekaliga. Founded in 1909 by Union Civil War veterans, the town’s attractive buildings reflect its historic origin. In fact, much of the effort to revitalize the town center has been devoted to restoring and maintaining the lovely Mission and Spanish Colonial architecture. One of the mainstays of the St. Cloud Main Street program is the monthly “Hipstoric 3rd Friday,” hosted by a different vendor every month. After the event, community members are invited to a free outdoor movie in nearby Centennial Park. Watch also for the annual Smokin’ Blues, Boats, Bikes & BBQ Fest as well as the Redneck Gala, which serves as a community fundraiser.

Venice Main Street

Venice is a beautiful, vibrant city on the edge of the Gulf of Mexico, just south of Sarasota. It is one of the few cities in the US designed by a renowned urban planner with the dream of creating a model city on the water. Its elegant Italian architecture, tree-lined streets, and landscaped town center—along with a series of visually arresting beaches—combine to make Venice an attraction for families, retirees, and vacationers alike. The town hosts art, music, and street festivals nearly every month, and there are a wealth of entertainment, dining, and shopping options in the thriving downtown retail core. In the food department, choices are ample, including French, Italian, seafood, BBQ, café fare, pub food, and creative American. There’s even an organic smoothie bar!

New Port Richey

Water and its natural beauty are abundant in New Port Richey, a sparkling city on the Gulf of Mexico with the Pithlachascotee River running through its heart. The town boasts 10 public parks, many with water access and opportunities to boat, kayak, fish, and hike. It’s not uncommon to see dolphins, turtles, and manatees around, as well as more than 140 bird species, which frequent the James E. Grey Preserve, an 80-acre wildlife sanctuary in town that is part of the Great Florida Birding Trail. A quaint historic downtown with arts, culture, retail, and dining completes the New Port Richey experience. Seek out Cavalaire Square for live music and authentic Caribbean fare every weekend or visit exclusive Dulcet Restaurant for fine dining nearby.

Do you have a thriving Main Street in your area? We’d love to know, share it with us in the comments section below.

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