Eat Like a Local, Drink Like a Local

O'Maddy's Restaurant in Gulfport FloridaAngry Pepper Restaurant in Seminole FloridaTarpon Tavern in Tarpon Springs Florida

This article is part of a series of pieces called “Detours” designed to send you just a little off the beaten path from the beaches and attractions of St. Pete/Clearwater, to discover other, lesser-known local favorites like family-run stores, unique galleries, and tantalizing restaurants. Read on and take a Detour into authentic St. Petersburg and Clearwater, Florida! 


This edition of “Detours” presents three independent, locally owned restaurant/bars—one each from different areas of St. Pete/Clearwater—that have built terrific reputations. All are within convenient driving distance of the Gulf Beaches. 

O’Maddy’s Bar & Grille, Gulfport 

O’Maddy’s sits on a corner of the main drag in the quaint old-Florida town of Gulfport. It looks out onto Boca Ciega Bay, is directly across the street from a long pier, and has a lush park right next door. 

Great location. Even better food, drink and vibe. 

The rustic place—with ample outdoor seating under umbrellas and a covered, open-air bar areafeatures big portions of hearty food; a full bar and mix of brand and local craft beers; live music; bustling lunches and happy hours; breakfast (yes, breakfast); and a party scene that goes well into the night. 

O’Maddy’s dates back to 1959 when Dottie and Eddie Stoehs opened Eddie’s Snack Bar. Thirty years later, they renamed the place after their daughter Madi. She and her husband Joe Guenther are now the owner/operators. “O’Maddy’s really took off when we started serving food seven days a week,” she says. That was 11 years ago. “We concentrate on value—reasonable prices, and you can count on going home with a to-go box.” 

One of O’Maddy’s signature dishes is Beef on Weck, a staple of Buffalo, N.Y., Joe’s hometown. It’s a sumptuous mound of warm, tender roast beef on a Kimmelweck roll with a side of au jus and horseradish. O’Maddy’s has a local baker make its traditional Buffalo buns according to a special house recipe. Now that’s commitment. 

The Angry Pepper Taphouse, Seminole 

Al Cowan is no social scientist, but he’s a staunch believer in “the third place.” That’s a theory that says people need a separate place from home (first place) and work (second place) in order to socially thrive. You could also call it a home away from home. 

Al and his wife Caroline have gone to great lengths to make The Angry Pepper Taphouse that third place for folks in a residential section of Seminole in mid-Pinellas County. Since taking over as owners in 2012, it’s safe to say that the couple has more than achieved their goal. 

The Angry Pepper is a neighborhood bar, a sports bar, a live-music-on-the-patio bar, a local-craft-beer-stocked bar, and a restaurant-bar with a smoker out back. Al calls the cuisine “Floribama”—which is basically a made-in-house blend of Sunshine State favorites, fresh seafood, and top-notch barbecue and other smoked delights. That means sumptuous smoked fish spread, pulled pork sliders, a to-die-for Smoked Brisket Rueben and more. 

The Angry Pepper has 34 beers on tap, including a generous selection from local micro-breweries. 

Tarpon Tavern, Tarpon Springs 

Dan Jenkin figured the last thing his adopted hometown of Tarpon Springs needed was another place serving gyros, souvlaki and moussaka. The county’s popular Greek community, with its rustic sponge docks and kitschy shops, has more than its share of Greek eateries.   

Dan chose a different path with the Tarpon Tavern in the downtown district, a few blocks south of the Hellenic-focused waterfront. It’s an American placewith food he describes as “traditional American that’s been brought up a few notches.” 

When he opened Tarpon Tavern four years ago, the big question was: Would the locals come? It didn’t take long to get an answer: absolutely. The restaurant/bar (emphasis on restaurant) has become a go-to place where locals mix easily with visitors. 

In Tarpon Tavern’s first year, Urban Spoon named it one of the Top 50 Bar/Restaurants in the U.S.

The 1920s-era building is painted an eye-catching ruddy pink. It features a homey interior and a breezy covered deck, each of which seats 50. 

Dan, a first-time restaurateur, came up with most of the menu items. The staples are burgers and sandwiches, along with salads, flatbreads, seafood and pasta. Behold the ultra-tasty Big Buffalo (pictured at the top of this page), a gargantuan stack of breaded, fried chicken bathed in buffalo sauce, topped with bacon and bleu cheese crumbles on a brioche bun. 

Dan proudly represents St. Pete/Clearwater’s booming craft brewery scene by serving a rotating array of locally produced beers.

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O'Maddy's Bar and Grille

City: Gulfport
Category: Dining

5405 Shore Blvd.
Gulfport, FL 33707

Phone: 727-323-8643

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Tarpon Tavern

City: Tarpon Springs
Category: Dining

20 N Safford Av
Tarpon Springs, FL 34689

Phone: 727-945-1000

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