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Our Picks: Fun Fall Festivals

Exploring everything, from hot-air ballooning to ski jumping amid prime foliage season to succulent stone crab, is on our list of top fall festivals this year.


Adirondack Balloon Festival [Glen Falls, NY] September 20–23

Arguably the largest free ballooning festival in the United States, the four-day Adirondack Balloon Festival offers both ballooning enthusiasts and novices the chance to experience what some have called “the closest sensation to floating.” The fall festival draws 150,000 to Lake George for the majestic spectacle of the balloons as they fill the sky, as well as food vendors, aviation displays, live music, and a craft fair.

Don’t Miss Get up at the crack of dawn on Saturday morning for the event’s largest balloon launch – up to 100 balloons will take flight.

Where to Stay The Sagamore Resort


Flaming Leaves Festival [Lake Placid, NY] October 6–7

Only in Lake Placid will you find stunning fall foliage juxtaposed with Olympic-caliber ski jumping talent. At the Flaming Leaves Festival, take in the spectacular show as soaring ski jumpers fill the sky, the trees are aflame in color, and live bands play a soundtrack of blues music. Delicious brews and tasty barbecue will fill you up while you play the lawn games and check out the specialty craft vendors.

Don’t Miss Be sure to take the combination chairlift and elevator ride up Whiteface Mountain to the top of the 120-meter ski jump for a million dollar panorama of brilliant red, yellow, and orange leaves that fill the Adirondack peaks.

Where to Stay Lake Placid Lodge

Clearwater Jazz Holiday [Clearwater, FL] October 18–21

Cool jazz and warm breezes make for a spectacular fall festival experience at the Clearwater Jazz Holiday. Acts like Dave Brubeck, Woody Herman, Dizzy Gillespie, Bonnie Raitt, The Avett Brothers, Dirty Dozen Brass Band, Bela Fleck, Amos Lee, and Trombone Shorty have all graced the stage in years past, making this four-day, four-night October fall festival a world-class live music extravaganza. Now in its 39th year, the festival draws tens of thousands of visitors each year to Coachman Park in Clearwater. After all, how often can you groove along to world-famous musical greats against the backdrop of one of the world’s best beaches?

Don’t Miss Kool & The Gang, Trombone Shorty & Orleans Avenue, Daryl Hall, Houndmouth, The Lone Bellow, and Gregg Allman are all on the lineup for this year.

Where to Stay Sandpearl Resort | Opal Sands Resort

Stone Crab Festival [Naples, FL] October 26–28

Naples is a natural fit for the two-day Stone Crab Festival to kick off stone crab season, considering the city is home to one of the largest stone crab fisheries in the world. The stone crab is best known for its massive, oyster-crushing claws, and those claws give it culinary cachet – it’s known as the tastiest crab in all the land (er, sea). For kids uninterested in cracking open claws, there’s face painting, bounce houses, balloon animals, and day cruises in Naples’s crystal-blue waters, where you might spot a dolphin or two.

Don’t Miss This fall festival kicks off with an annual “Cracking of the Crab” kick-off dinner at Pincher’s Crab Shack on Friday before launching into a two-day block party at Tin City, a series of historic buildings turned into an open-air market. Between bites of stone crab, wander the 40 eclectic shops or jump aboard one of the charter boats that take guests out for short harbor tours.

Where to Stay Edgewater Beach Hotel


Feast of Little Italy [Jupiter, FL] November 2–4

Ever been to a big Italian family party? That’s essentially what this three-day event is – except it centers around the entire community, whether your ancestors came from the boot-shaped peninsula or not. Held in the Abacoa Town Center, the street festival, now celebrating its 16th year, brings scores of music, art, and bocce – one of Italy’s oldest games – to sunny shores of Jupiter. As for the food, vendors lining the streets serve every type of Italian dish imaginable, from sausage and peppers to eggplant parm to fried ravioli and spaghetti and meatballs. For the bambinos, expect games and a kid-sized roller coaster.

Don’t Miss In the Galbani La Cucina Italiana Cooking Pavilion, national and well-known local chefs make authentic Italian specialties right before your eyes and under your nose. Think creations like Caprese pancetta tacos, fresh mozzarella roasted potato salad, and a s’more mozzarella panini featuring fresh mozzarella, chocolate hazelnut spread, banana, walnuts, honey, sugar, and vanilla.

Where to Stay Jupiter Beach Resort & Spa

Bacchus on the Beach [Longboat Key, FL] November 8–9

Winemakers from around the world converge on Florida’s Gulf Coast for two nights of special wine dinners at the Resort at Longboat Key Club. Saturday night sees three different wine dinners hosted at different spots around the resort; Sunday’s consists of a “stone crab celebration” plus samplings from the hundreds of wine selections on hand for the event.

Don’t Miss The Pigs & Vino dinner on Saturday delivers the full bacchanalian on the beach experience, with the “pig” theme’s variety of pork dishes plus whole pig barbecue in the Island House tent.

Where to Stay Resort at Longboat Key Club

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