This Upscale Neighborhood Proves There's More To Jacksonville Than Its Boring Reputation

Jacksonville, Florida, spreads across more land and water than any other U.S. city outside Alaska, covering 874 square miles, according to Jacksonville Today. You would think there'd be something to do in such a sprawling city, and you'd be right, but you might not know that if a certain personal finance website were your only bellwether for travel. That's because Jacksonville is also America's most boring city, per FinanceBuzz. It was one of 75 cities that the site measured against each other using five metrics: population makeup, culinary scene, outdoor activities, nightlife and celebrations, and things to do.

Going by those metrics, Jacksonville earned an "excitement score" of 14.3 out of 100. FinanceBuzz notes that over 50 percent of the city's restaurants are chains, and it has the third-lowest rate of nightclubs in the country. This is due in part to Jacksonville's low population density relative to its size. Not every neighborhood is concentrated around the kind of shopping and dining destinations that would appeal to locals and tourists alike. However, there's still plenty to see and do in Riverside and Avondale, two upscale historic districts that are often considered one big neighborhood.

Riverside and Avondale are both on the National Register of Historic Places, thanks to their domestic architecture, which exhibits a mix of Colonial Revival and other styles, including the most craftsman bungalows in Florida. The combined neighborhood sits on former plantation land, where residential streets sprang up following the Civil War. An influx of wealthy residents, who lost their downtown homes during the Great Fire of 1901, helped transform Riverside Avondale into the architecturally significant neighborhood it is today. If looking at houses isn't your idea of a good time, there's no better place to start exploring the neighborhood than by the actual riverside.

One of Jacksonville's best museums originated as a riverfront home, so visiting at least one old house might be inescapable for art lovers in Riverside. The Cummer Museum of Art & Gardens is situated along the St. Johns River on property that once belonged to Ninah Cummer, who contributed the first 60 pieces to a collection that now encompasses over 5,000 works. The permanent collection includes Florida art, Japanese woodblock prints, and 1920s movie posters from Jacksonville's Norman Studios. In addition to special exhibitions, the museum hosts workshops and events, such as a summer residency with nights themed to different genres of American roots music.

Like the Cummer Museum's lush gardens, the rooftop lounge at River & Post — located just down the street — offers views of the St. Johns, along with downtown Jacksonville's skyline. If the lounge's buffalo chicken flatbread and pulled pork nachos aren't enough to whet your appetite, head down to the restaurant on the ground floor. A weekend brunch of huevos rancheros or weekday lunch of shrimp, sausage, and smoked gouda grits might restore your faith in the city's dining. River & Post took up residence in a Riverside office building in 2017, and it's just one example of how Jacksonville's culinary scene is evolving beyond chain restaurants.

At Riverside's Keg & Coin, you can sip craft beer and play pinball and vintage arcade games like Street Fighter II and the original Teenage Mutant Ninja Turtles. In the morning, Brew Five Points will get you fed with breakfast tacos, but the real highlight might be the locally and regionally brewed coffee. That includes Bandit Staple Blend drip coffee from St. Petersburg, Florida, and the "Not Bad" blend of cold brewed iced coffee from Jacksonville's The Flamingo. Brew Five Points also makes their own dark hot chocolate in-house, and they offer lattes made with "hand whisked ceremonial matcha" (per their website) from Shizuoka, Japan.

Another thing that FinanceBuzz counted against Jacksonville was its low rate of concert venues per capita. This might create some cognitive dissonance for Floridians who have been drawn into the city by a concert in Moran Theater at the Jacksonville Center for the Performing Arts. Either way, a lack of concert venues isn't as much a problem anymore in Riverside's Five Points area. Sun-Ray Cinema, which took up the mantle of the historic Riverside Theatre (the first movie theater in town to transition from silent film to "talkies"), closed in 2024. In its place is Five, a cashless concert hall that now displays the names of musical artists instead of movie titles on the old theater marquee.

The concert hall is in the same building as the aforementioned Brew Five Points coffeehouse. If you book the VIP Projector Room at Five, you'll be sitting where the theater's projection booth once was. Riverside Avondale is also an antique shopper's paradise, with over 20 dealers selling collectibles like vinyl records out of stalls at the 5 Points Antiques market. Stroll along St. Johns Avenue in Avondale, and you can also browse shops like Avenue Antiques. Dining destinations include Brick Restaurant, which brings live music to Avondale, too. Steak, seafood, rice bowls, and burgers are on the menu, with the prime rib poblano pepper quesadilla being a good starter.

In all fairness to Jacksonville, one of the best U.S. destinations for music lovers — Memphis, Tennessee — ranked as the fifth most boring American city on FinanceBuzz's list. It was followed at number six by San Antonio, Texas, a must-visit destination for history buffs. As should be clear by now, you can find both music and history (in the form of architecture, art, and antiques) in Riverside Avondale. It's a fun, walkable neighborhood that helps make greater Jacksonville one of the most overlooked spots in Florida.