Seaside

Seaside, Florida is the town that started it all. Founded in 1981 as the first New Urbanist community in America, this 80-acre beach town on Scenic Highway 30A became famous for its pastel cottages, white picket fences, and walkable town center — and then became world-famous as the filming location for The Truman Show. Four decades on, Seaside is still the beating heart of 30A, and no first visit to South Walton is complete without an afternoon here.

The town is built around Central Square, a semicircle of shops and restaurants facing the Seaside Amphitheater, a grassy lawn that hosts concerts, outdoor movies, and community events throughout the year. Across the street, the iconic silver Airstream food trucks line 30A, serving everything from Wagyu hot dogs at Wild Bill’s Beach Dogs to shave ice at Frost Bites. Browse Sundog Books and Central Square Records, pick up picnic supplies at Modica Market, and finish at Bud & Alley’s rooftop bar for a Gulf-front sunset — a Seaside ritual since 1986.

Where Is Seaside on 30A?

Seaside sits near the midpoint of Scenic Highway 30A in South Walton County, between WaterColor and Grayton Beach to the west and Seagrove Beach to the east. The sugar-white beach is reached through Seaside’s distinctive wooden pavilions — each one designed by a different architect — and the paved Timpoochee Trail runs straight through town, making Seaside one of the easiest places on 30A to explore by bike.

Tips for Visiting Seaside

Seaside is the busiest spot on 30A, and parking along the town center fills by mid-morning in summer and on holiday weekends. Arrive early, or better yet, park in a neighboring community and bike or walk in on the Timpoochee Trail. Spring and fall bring warm Gulf water, thinner crowds, and the best weather of the year; summer is lively and family-packed; winter is quiet and locals-only. Beach access points are public along the pavilions, though seating on the sand in front of the town is largely reserved for guests in season. However long you stay, Seaside rewards slowing down — this is a town designed to be strolled.