Amble Along Islamorada's Old Highway

For most of the 125-mile expanse of the Florida Keys there’s one road in and one road out — U.S. 1. There are a few exceptions and Old Highway in Islamorada is a not-to-be-missed gem for walkers and runners, especially those that like a bit of diversion along the way. 

Islamorada’s Old Highway, also known as Old Road or officially, State Highway 4A, provides a welcome respite from the traffic on U.S. 1 along with scenic views and access to some of the Upper Keys’ choicest breweries, art galleries, restaurants and shops. 

The road is sectioned off into several segments due to bridges and other obstructions.

The first section begins just past Coral Shores High School, mile marker 89.9, and is the location for the recently revived Old Highway 5k Run/Walk that takes place in November. 

This section is residential on the Atlantic Ocean side. On the side facing the main road, walkers have access from the back side to pleasant spots like Old Road Gallery, specializing in pottery, bronze and copper sculpture, with a shady sculpture garden complete with a showy peacock.  

Several restaurants on this section of the road might tempt walkers and runners away from workouts. M.E.A.T. Eatery and Taproom at mile marker 88 has won awards and legions of fans for its burgers, wings and house-made condiments. 

The main Old Highway section favored by those out for a stroll or a serious walk or run, interspersed with many pleasant stops and diversions, begins after the Whale Harbor bridge at mile marker 83.4 and continues to where the road rejoins U.S. 1 at mile marker 80.5.

Islamorada’s Hurricane Monument at mile marker 81.8 commemorates the more than 400 people who perished in the 1935 Labor Day hurricane. Ceremonies are held here on the solemn anniversary of the storm and on other important days such as Memorial Day. 

This route is a favorite for guests of resorts including the Islander, Cheeca Lodge and The Moorings Village, among others. It provides access to the popular Morada Way Arts and Cultural District, widely known for its Third Thursday Art Walk evening events that take place year-round.

You don’t have to wait for the monthly art walk to explore galleries that are open most days, such as Roberto “Pasta” Pantaleo’s Islamorada Art by Pasta, Taylor Hale Fine Art, Gyotaku by Lisa Lee, Jessica Ann Art and many more. 

It’s easy to reach an eclectic variety of shops from resorts and vacation rentals along Old Highway, including Ocean Gardens and Gifts, Sea Dragon Furniture, World Wide Sportsman, Banyan Tree Garden & Boutique and Miss Monroe Boutique. 

Just before Old Highway rejoins U.S. 1. you’ll find Midway Café, a popular spot for breakfast and lunch with shaded outdoor seating on the Old Highway side. 

Difficulty level: Easy 
Best for: Exercise and art enthusiasts, shoppers
Admission: Free
Address: Various sections between mile markers 89.9 and 80.5
Nearby lodging: Cheeca Lodge and Spa, Islander Resort, The Moorings Village, La Siesta, Pines & Palms Resort
Nearby dining: M.E.A.T. Eatery & Taproom, Marker 88, Islamorada Brewery & Distillery, City Hall Café, Lorelei Restaurant & Cabana Bar, Kaiyo Grill & Sushi, Chef Michael’s, Green Turtle Inn, Square Grouper, Midway Café, Lazy Days, Papa Joe’s