Coolest Block in Dunedin: Walking Main Street, Day and Night

By Janet K. Keeler

Dunedin, Fla., is some kind of wonderful.

Whether it’s by sheer happenstance or smart business design, Dunedin (pop. 36,000) has succeeded in maintaining its small-town charm while putting out the welcome mat for visitors.

Its walkable Main Street is a tangle of unique restaurants and watering holes (some dog friendly like Skip’s Bar & Grill), interspersed with boutiques hawking jewelry, arts and crafts, plus tropical home décor that tells the world you’ve been to Florida. Yes, that’s means palm trees and flamingos. Park the car and spend the day, no reservations necessary.

Dunedin isn’t necessarily one of those places on a traveler’s bucket list, situated as it is in the middle of heavily populated Pinellas County and 25 miles from Tampa.

It’s on the Intracoastal Waterway, and boasts fabulous sunsets and an abundance of craft beer, with perhaps more breweries per capita that any other city in the state. It also offers a beach on fabulous, pristine Caledesi Island, accessible only by ferry or boat.

The explosion of artisan beer in Florida has rolled into Dunedin big time. Dunedin Brewery lays claim to being the oldest microbrewery in Florida and Caledonia Brewing on Main is among the newest. In between there is 7venth Sun Brewery, Woodwright Brewing Company, and Cueni Brewing Company.     

An amble through Dunedin might start (and end) with a brew at Caledonia, housed in a 1925 building that is the former home of the Dunedin Times newspaper. Caledonia opens at noon and closes down at midnight. There’s no food but a shelf of board games keeps patrons and their underage kids occupied. 

As with most microbreweries, there are seasonal offerings but a taste of El Diablo Guapo Mexican Lager could put you in the mood for a meal at Casa Tina Mexican Restaurant, one of Dunedin’s most popular eateries a short stroll away. Inside, the bright pink walls are covered with Day of the Dead art in many forms, vintage photos of Mexican landscapes and people, plus lots of vestiges of Frida Kahlo, the iconic artist. There’s art on the plate, too, including mole poblano, one Casa Tina’s most popular dishes. The house margarita is a top-seller, too. 

Lucky you’re walking. Fueled with a beer and a margarita, it’s time to hit some of the Main Street stores or the Dunedin Downtown Market in Pioneer Park if you are visiting on a Friday or Saturday. The pretty park turns outdoor bazaar then, and besides fresh produce and prepared food, be on the lookout for pottery, art, artisan dog treats, candles, and even orchids.         

There are still plenty of places to browse even if you’ve hit Dunedin on another day of the week. The Pinellas Trail, a 38-mile jogging, biking, skating and walking trail that runs nearly the length of the county, cuts across Main Street. It’s not unusual to see people in their athletic clothes sitting in restaurants or walking through stores. There are places to lock up bicycles.           

Near the Pinellas Trail is the Clay and Paper Gallery of Art, a wonderland of jewelry and pottery, plus wall and garden art in many mediums. A ceramic grouper swimming across your wall at home will broadcast that you’ve been to Florida, and that whirligig in the rose garden? A reminder of a happy vacation for sure. The gallery also hosts regular events including wine nights and artists’ receptions.           

There are some fun vintage shops that will gobble up lots of your time as you ruffle through old clothes, linens, home décor and silverware. Amanda Austin and My Favorite Things have their own flavor and are easy walks from Pioneer Park.          

Nancy’s Fancy shop back on Main Street is one of those places that gets a hold of a certain type of shopper and doesn’t let go. The baubles! The scarves and wraps! The oh-so-cute reading glasses that make getting older better! A serious saunter through this shop could net all the gifts you need to buy for the year.           

All this shopping and lookie-looing should put any visitor in the mood for chocolate. (The effects of the beer and margarita are long gone by now.) You won’t have to go far from Nancy’s to the intersection of Broadway and Main where you can pick from a Salted Chocolate Carmel cone at Strachan’s Ice Cream or exquisite dark chocolate-covered hazelnuts (and more) at Viktoria Richards Chocolates. Dunedin Coffee Company & Bakery satisfy those chocolate cravings, too.            

In many ways, Dunedin is not your typical small town, mostly because the businesses don’t go to sleep with the sun goes down. Two veteran Dunedin restaurants, the Crown and Bull (formerly Kelly's) and the Black Pearl, sit side by side. The Black Pearl is a fine dining dinner establishment; the Crown and Bull, open until the wee hours seven nights a week, features modern American dishes made from scratch with seasonal local ingredients. Offerings include prime rib, corned beef, sauerkraut, and purple kimchi. And make sure to sample their famous dill pickles!