The Man Who Built 100+ Pensacola Buildings, Plus 12 Local Events

Good Morning, Pensacola! Last week we talked about who built downtown over the past decade. This week, we're going back a little further. Like, 467 years further.

In today's line:

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- The Bay Line Crew

When people think about the first European settlement in America, they usually say Jamestown (1607) or St. Augustine (1565). They're wrong. Pensacola was first by 48 years - 1559.

The settlement lasted exactly one month before a hurricane destroyed it, which is probably why it doesn't make the history books. But the attempt happened, and it happened here.

Tristán de Luna y Arellano led that first expedition. Spain sent him with 1,500 people to establish a colony that would anchor their claim to Florida. They landed somewhere near present-day Emanuel Point, probably around what is now East Hill. A month later, a hurricane sank most of their ships and destroyed their supplies (because in a huge blunder de Luna let the people relax instead of immediately taking contents to shore). By 1561, Spain gave up and pulled everyone out.

The settlement was completely forgotten until 1992, when archaeologists found ship remnants in Pensacola Bay. DNA testing in 2015 confirmed those were de Luna's ships. You can see artifacts from that expedition at the T.T. Wentworth Jr. Florida State Museum downtown.

The People Who Actually Built What We See Today

Pensacola had multiple false starts. The Spanish came back in 1698 and established a permanent fort. Then the British took over from 1763 to 1783. Then the Spanish again. Then finally the United States in 1821. The city changed hands so many times that it earned the nickname "The City of Five Flags."

But the Pensacola we recognize today was built by people who came later, in the 1800s and early 1900s.

William D. Chipley is probably the most important person you've never heard of. He moved here in 1877 and became obsessed with connecting Pensacola to the rest of Florida by railroad. At the time, getting from Pensacola to Jacksonville took weeks by ship around the Florida coast. There was no direct land route.

Chipley spent the next decade building the Pensacola and Atlantic Railroad, which finally connected Pensacola to the rest of the state in 1883. That railroad changed everything. Suddenly timber and naval stores could be shipped efficiently. The lumber industry exploded. Jobs followed. Population followed. Chipley Avenue downtown is named after him.

Without that railroad, Pensacola probably stays a small coastal outpost instead of becoming Northwest Florida's largest city.

William H. Chase is a more complicated figure. Chase was an Army engineer who built Fort Pickens in the 1830s. He also helped develop Pensacola's early infrastructure and economy. Chase Street is named after him.

But Chase married into a wealthy slave-owning family, the Duvals, and he owned large plantations worked by enslaved people. He used enslaved labor (rented through the US Army) to build Fort Pickens. When the Civil War started, he sided with the Confederacy.

John Sunday is a person whose story deserves attention. Sunday was born enslaved in Pensacola around 1828. During the Civil War, he escaped and fought for the Union Army with the 82nd United States Colored Infantry. After the war, he returned to Pensacola and became a carpenter.

Over the next 40 years, Sunday built more than 100 buildings in Pensacola. He became one of the first black state legislators in Florida during Reconstruction. He bought property all over the city. By the early 1900s, he was the wealthiest black man in the South.

He built the Sunday School for black children. He funded St. Joseph's Catholic Church. He owned rental properties, commercial buildings, and developed entire blocks of the city. When he died in 1909, his estate was valued at over $80,000, which would be several million dollars today.

Sunday's buildings are still standing. The old Pensacola Journal building, commercial properties on Palafox, houses in East Hill. You've probably walked past his work dozens of times without knowing it.

There's no major street named after John Sunday. No prominent statue. Most people who live here have never heard of him.

Here are a few places you can see this history:

Nothing in this section is sponsored. They’re just the things you need to know. I’ll always let you know when something’s sponsored.

Santa Rosa Beekeepers Meeting - March 19, 6:00-8:00 PM - 6263 Dogwood Dr., Milton. Jimmy Davis, the state apiary inspector, will share insights on the latest hot topics in beekeeping. All beekeepers and the bee-curious are welcome. Potluck dinner from 6:00-7:00 PM. Free.

Pensacola Beach Brawl - March 21-22 - Pensacola Beach. They call it "the fittest beach party in the world." It's a fitness competition on the beach with workouts, vendor village, and live music. Whether you're competing or just watching, it's a scene. Registration required for competitors, free to spectate.

Gallery Night Pensacola - March 21, 5:00-9:00 PM - Monthly downtown art walk featuring 15+ galleries and studios. Free event, galleries concentrated on Palafox between Garden and Main. Some galleries serve wine. Parking in lots off Palafox or street parking (free after 6 PM).

Resin Table Workshop - March 21 and 22, 1:00 PM - Flip Flops on Palafox. Design and create your own custom resin side table. All materials included. $90 per student, registration required.

Palafox Market - March 22 and 29, 9:00 AM-2:00 PM - Downtown Pensacola, Martin Luther King Jr. Plaza. Weekly farmers market with local vendors selling produce, baked goods, prepared food, plants, and local art. Gets crowded by 10 AM. Free to browse.

Best Beach Bash - March 27 - Pensacola Beach. Beach celebration with live music, vendors, and activities. Details still being finalized but it's shaping up to be a solid beach day event. Free admission.

Books by the Bay Book Festival - March 28, 10:00 AM-4:00 PM - Community Maritime Park. Northwest Florida's largest literary festival featuring 100+ authors, book signings, panel discussions, kids activities, and food trucks. If you read books, this is worth going to. Free admission.

Pensacola Symphony Orchestra: Masterworks IV - March 28, 7:30 PM - Saenger Theatre. The symphony is performing Brahms' Symphony No. 1 plus other classical pieces. If you've never been to the symphony, this is a good one to start with. Tickets vary by seating.

UWF Historic Trust Dinner: Pensacola & The American Revolution - March 30, 6:00 PM - Pensacola's role in the American Revolution is not something they taught us in school, but it happened. This dinner features a presentation on that history. Tickets required, check their website for pricing and reservations.

Blue Angels Practice - March 31, 10:30 AM - National Naval Aviation Museum, NAS Pensacola. First practice of the 2026 season. Public viewing at the museum. Practice typically starts at 10:30 AM, public access 9 AM to 3 PM through West Gate on Blue Angel Parkway only. Bring sunscreen. Parking fills up early. Free.

Pensacola Beach Market - March 29, 9:00 AM-2:00 PM - Casino Beach parking lot, Pensacola Beach. Weekly market with 30+ vendors. Good for fresh produce, baked goods, and local art. Coffee stand at the entrance is solid if you need caffeine. Free to browse.

Gulf Breeze Festival of the Arts - March 28-29, 10:00 AM-4:00 PM - Gulf Breeze. This event hosts 100+ local, regional and national fine artists, a local artists art show, silent auction, student art show, and food vendors. They have live artist demonstrations and kids activities. Free admission.

Nothing in this section is sponsored. They’re just the things you need to know. I’ll always let you know when something’s sponsored.

Once a month we want to share two local clubs or organizations where you can meet people and do something interesting.

Pensacola Aviators Rugby Club

What it is: Men's and women's rugby teams that practice and play matches locally and regionally. Rugby is one of those sports that builds a tight community fast. The club has been around since the 1970s and they're always looking for new players. They also host social events and tournaments.

Who it's for: Anyone 18+ who wants to try rugby. No experience required. They'll teach you.

Commitment level: Practices are Tuesdays and Thursdays, 6:30-8:00 PM at Bayview Park. Games are typically on Saturdays during season (spring and fall). You can show up to practice without joining immediately.

Cost: $100 annual club dues, plus you'll need to buy a jersey and basic gear (around $50-75).

Who this is NOT for: If you're not interested in contact sports or don't want to commit to twice-weekly practices during season, this probably isn't your thing.

How to join: Show up to practice at Bayview Park (2000 E. Lloyd St.) on a Tuesday or Thursday, or check their Facebook page for contact info.

Newcomers Club of Pensacola

What it is: Social organization for people new to the Pensacola area. Been around since 1965. Moving to a new city is hard. This is one of the easier ways to meet people without it feeling forced. The interest groups are where real friendships tend to form.

Who it's for: Anyone who moved here within the past few years and wants to meet people. Skews a bit older (40s-70s) but younger members are welcome.

Commitment level: Monthly luncheons (usually second Thursday of the month) plus optional interest groups like book club, dining out, cards, and day trips. You participate as much or as little as you want.

Cost: Annual membership is around $30-40 per household.

Who this is NOT for: If you've lived here your whole life or prefer making friends organically over time, you probably don't need this. Also, if structured social events aren't your thing, you'll find this awkward.

How to join: Check their Facebook page (Newcomers Club of Pensacola) or show up to a monthly luncheon as a guest. They meet at various restaurants around town.

March 21 - Third Day @ Pensacola Bay Center - Listen here

March 28 - Pensacola Symphony Orchestra: Masterworks IV @ Saenger Theatre - Listen Here

April 1 - Santana: Oneness Tour 2026 @ Pensacola Bay Center - Listen here

April 3 - Anthony Hamilton @ Pensacola Bay Center - Listen Here

April 4 - White Tie Rock Ensemble @ Pensacola Bay Center - Listen Here

April 18 - Brandon Lake @ Pensacola Bay Center - Listen here

August 22 - Vince Gill: 50 Years From Home @ Saenger Theatre - Listen here

Thanks for being here. We appreciate you taking the time to read the Pensacola Bay Line today.