Coming from San Marco or Downtown, cross the Fuller Warren Bridge, and get off on the first exit (351A for Park Street), to get to Riverside. From the exit, turn left and drive for a short bit till you hit Jacksonville’s historic and ridiculously popular 5 Points, named so for the star-like criss-cross of roads that intersect at the heart. I really can’t say enough great things about 5 Points. It’s very bike, scooter, and pedestrian friendly and because of that, you’ll have an easy time finding your niche of regular hangouts filled with people you’ll get to know sooner or later.
5 Points hosts a popular monthly event called First Fridays at 5 Points where the streets are occasionally closed off to traffic to make it more conducive for large crowds. It’s home to antique stores, coffee shops, eateries, a natural food store, bars* and clubs*, parks, art galleries, and fantastic selective vintage clothing stores. Some of my favorites include Birdies* for live shows, Hovan Mediterranean dining, Grassroots Natural Food Store, Vintage Recalled, The Clothing Warehouse, New Broadway Square cafe, Fans & Stoves antiques, and Sushi Cafe. 5 Points also hosts various mini music, art, and year-round holiday festivals.
The 5 Points Theatre hosts not only newly released movies, but also old classics, cult classics, and random interesting events like the Jacksonville Film Fest, Citrus Cel Animation Fest, and Pecha Kucha just to name a few.
Right near 5 Points with its mesmerizing riverfront view, Memorial Park is a great wide open space where groups of people organize such events like weddings, tight-rope-walking, dog shows, Jacksonville’s own Critical Mass and Alley Cat cyclist events, and various group sport events like kickball, flag foot ball, rugby, and soccer.
Go north on Riverside Avenue from Memorial Park and you’ll reach The Cummer Museum of Art & Gardens. The Cummer is also located right on the River with a gorgeous garden out back for romantic strolls with your crush. Just beyond that, each Saturday morning, for about ten months out of the year you can find local fresh fruit and vegetable vendors, arts and crafters, and entertainers at Riverside Arts Market held underneath the Fuller Warren Bridge.
Going west you’ll find tons of gorgeous homes with great character and huge old trees, quite indicative of what you’d expect to see up north. If you stay on Park Street you’ll hit another little crossroads known as Whiteway Square. Get lost in the Riverside neighborhood as you make your way a little further northwest to the environ of Murray Hill or southwest to the environ of Avondale. Check out The Shoppes of Avondale located on St. Johns Avenue, another quaint and popular little square of unique stores, bars*, and restaurants including The Casbah, The Brick, and Eclipse*.
For a good way to keep up to date with great venues and fun events read: Folioweekly or The Florida Times Union.
My favorite online go-tos include:
*Please note, neither I, nor The University of North Florida, in any way supports or promotes underage drinking. For those old enough, drink responsibly and never drink and drive.