15 Best Things to Do in Fort Walton Beach (FL)

John Beasley Park

On the Florida Panhandle’s Emerald Coast, this city is my idea of a dream beach destination. The shoreline on Okaloosa Island, with its sugar-white sands and twinkling clear waters, needs to be seen to be believed.  On the gulf here you can choose between natural, undeveloped beaches, and all the fun of the Okaloosa Island …

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15 Best Things to Do in Oldsmar (FL)

Mobbly Beach Park

In 1916, Oldsmobile founder Ransom Eli Olds bought up this land at the north end of Tampa Bay to build a planned city.  Despite a huge marketing push, this was a financial disaster for Olds. His oil well never yielded any oil, and the proposed city of 100,000 had only attracted 200 people when he …

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15 Best Things to Do in Lady Lake (FL)

Spanish Springs Town Square

In the very northwest of Lake County, Lady Lake is a town with a population that has more than doubled since 1990. Part of that growth can be explained by The Villages. Set next door, this vast retirement community resembles a full-fledged city, and has a series of public districts that non-residents are free to …

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15 Best Things to Do in Middletown (CT)

Harbor Park

Resting on the west bank of the Connecticut River and dating back to 1650, Middletown is a mid-sized college city with a manufacturing and shipping past. Middletown’s life is mostly concentrated on the tree-lined Main Street. One block in from the river this artery is traced by restaurants, bars and coffee shops. Downtown Middletown is …

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15 Best Things to Do in Stratford (CT)

Short Beach

Dating right back to 1639, Stratford is a town on Long Island Sound bounded to the east by the final reach of the Housatonic River. At the Housatonic’s mouth, and around the coast, you can lie back on public beaches. One of my favorite places to watch the sun go down is right here, on …

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14 Best Things to Do in Callaway (FL)

John B. Gore Park

Sitting beside the picture-perfect East Bay, Callaway is a small residential city just outside of Panama City.  With a short drive you can reach the sandy shores of Panama City Beach, or downtown Panama City, with its dining, shopping and farmers’ markets.  I adore St. Andrews Bay, renowned for its large pod of bottlenose dolphins …

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15 Best Things to Do in Niceville (FL)

Niceville Skate Park

At the head of Choctawhatchee Bay, Niceville is a city that got its cheery name in 1910. Before then, this place was called Boggy, so I reckon you can see why they made that choice. Boggy comes from the Boggy Bayou, which is a picturesque watercourse feeding into the bay. Fringed by pine flatwoods, these …

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15 Best Things to Do in Mount Dora (FL)

Donnelly House

Nestled on the eastern shore of Lake Dora is a lovable little city, with a cozy downtown made for strolling.  Dating back to the 1880s, Mount Dora gets its name from the plateau that it sits on, and has earned the nickname, Festival City. I’d say this is a pretty accurate monniker, as the spring …

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15 Best Things to Do in Auburndale (FL)

Auburndale City Park

Home to almost 20,000, this small but growing city is in a scenic part of Central Florida, defined by its lakes. In fact, almost 40% of Auburndale’s area is open water. Many of Auburndale’s lakes are framed by residential developments or RV resorts. The biggest of these is Camp Margaritaville, with an easygoing island-style atmosphere. …

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15 Best Things to Do in Marco Island (FL)

Cape Romano

Between mangrove-lined bays and the Gulf of Mexico, Marco Island is a city on the namesake barrier island.  This is the largest island of a chain known as the Ten Thousand Islands, stretching for more than 70 miles down to Cape Sable. Starting in Marco Island you can spend unforgettable days paddling in mangrove tunnels, …

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