Expert Connection
Gulfport

Second Street Historic District, Gulfport Neighborhood

Gulfport in Mississippi offers a delightful, peaceful setting with minimal street noise and a calm atmosphere. The area features predominantly two and three-bedroom homes built around 1987, with many single detached houses as well as smaller apartment buildings. Accessibility is convenient, with easy car parking and many supermarkets accessible by vehicle. Pharmacies and primary schools are generally easy to reach without a car, contributing to everyday convenience. A selection of nearby restaurants adds variety to dining options. Educational needs are met through both public and private schools serving elementary and secondary levels, providing a balanced community environment.

Gulfport offers a relaxed environment. Gulfport is very quiet overall, as the streets are usually very peaceful.

Highlights of Second Street Historic District

Parks, schools, dining, and what makes this neighborhood special

🏡 Charming Historic Homes

Second Street Historic District is famed for its beautifully preserved early 20th-century homes, featuring Craftsman bungalows and Queen Anne cottages lining Second Street, showcasing Gulfport’s architectural heritage and offering a picturesque, walkable backdrop for the community.

🎨 Gulfport Arts Center

Located just steps from Second Street, the Gulfport Arts Center hosts exhibitions, art classes, and cultural events that bring together neighbors and local artists, enhancing the area’s creative spirit and providing a hub for community expression.

🛣️ Historic Brick Sidewalks

The original brick sidewalks along Second Street preserve the district’s old-town charm, making the neighborhood ideal for leisurely strolls while appreciating the history and craftsmanship that shaped Gulfport’s early urban landscape.

🍴 The Chimneys Restaurant

A beloved dining spot on Second Street, The Chimneys serves Gulf Coast cuisine with a view of towering oak trees and the water, blending elegant Southern fare with the district’s unmistakable atmosphere and history.

🌳 Second Street Community Park

This pocket park is a gathering place for families and pet owners within the district, offering shady green space, benches, and a peaceful spot for social events, picnics, and neighborhood gatherings right in the heart of Second Street.

A Gulfport Neighborhood

This October in Second Street Historic District

Things to do, events, and what's happening this month

October 3–4, 2026

View the Cruise 2026

Downtown Gulfport • Saturday sunset concert; Sunday 8:00 AM–5:00 PM

This annual downtown Gulfport festival is especially convenient for Second Street Historic District residents, with classic cars, vendor booths, food, and live entertainment close to the district. It is an easy walk-or-short-drive way to enjoy the opening weekend of Cruisin’ the Coast without leaving central Gulfport.

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October 4–11, 2026

Cruisin’ the Coast 30th Anniversary

Jones Park and locations throughout Gulfport and the Mississippi Gulf Coast • Various times; Gulfport activities begin October 4

Gulfport residents can enjoy one of the Coast’s biggest annual spectacles, with thousands of classic vehicles, cruise-ins, music, food, and special activities. Jones Park serves as Cruise Central, making the event a particularly accessible outing from Second Street Historic District and downtown neighborhoods.

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October 7, 14, 21, and 28, 2026

Gulfport Harbor Farmers Market

Jones Park Barksdale Pavilion • 9:00 AM–1:00 PM

The weekly Harbor Farmers Market offers a relaxed midweek outing near downtown Gulfport, with seasonal produce, prepared foods, and handmade goods. Residents of Second Street Historic District can combine a market visit with a walk along Jones Park and the harbor, making it useful for both shopping and leisure.

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October 16, 2026

Depot District at Dusk

Downtown Gulfport • 4:30 PM until dusk

Depot District at Dusk brings live music, local vendors, shopping, and restaurant specials into the heart of downtown. Its free, family-friendly format makes it an easy evening activity for Second Street Historic District residents who want to support local businesses, meet neighbors, and enjoy Gulfport’s historic core.

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October 23–24 and 30, 2026

Tricks, Treats & Trains

TrainTastic • 5:30 PM–7:30 PM

TrainTastic’s Halloween evenings offer Gulfport families trick-or-treating, carnival-style games, costumes, themed train rides, and a Haunted Depot. Located on Pass Road, it is a practical nearby seasonal outing for residents of the historic district, with an indoor component that helps make Gulf Coast October weather less of a concern.

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From the Neighborhood

Stories, updates, and things to know in Second Street Historic District

Know Your Neighborhood

Local characteristics and demographics for Second Street Historic District

Neighborhood Characteristics

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Demographics

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