6 Best-Kept Travel Secrets of the September-October Shoulder Season

From beachfront bites (at a fraction of the price) to backcountry hikes, these are the signature experiences you’ll only find across Opal destinations during the golden stretch of September through October.

What is shoulder season? Tucked between summer’s peak tourist crowd and the end-of-year holiday rush, the period of September through October is something of the unsung hero of travel seasons, offering a kind of golden quiet where the weather’s still in your corner, the crowds have thinned, and your pick of Opal Collection accommodations are far more likely to be available (yes, even the suites with the best views).

But the beauty of shoulder season isn’t just the vibe at the resorts – it’s also what’s happening outside their doors. This is when Opal Collection destinations come alive in their own unexpected ways: when Key West throws its most colorful street party of the year, when Lake George hiking trails offer some of the best crystal-clear views, and when Acadia’s Cadillac Mountain sunrise can be savored without a reservation. Here are six highlights you can only experience during this unique time of year.

SUNSETS HIT DIFFERENT IN CLEARWATER BEACH

You haven’t really seen a Gulf Coast sunset until you’ve caught one in Clearwater Beach in September or October. During these months, the position of the sun shifts lower on the horizon earlier in the evening, and the air often holds a delicate balance of moisture and clarity. This combination causes sunlight to scatter differently than in summer, amplifying the rich reds, purples, and oranges that paint the sky. The result? Longer-lasting, more vivid displays that feel almost cinematic – especially when mirrored on the calm Gulf waters. Add in the peaceful ambiance of the season, and each evening becomes its own natural masterpiece.

• Where to Stay in Clearwater Beach: Opal Sands Resort | Opal Sol | Sandpearl Resort 

SARASOTA’S ART SEASON STARTS UP

While the beaches are still basking in warm Gulf waters, Sarasota’s cultural calendar kicks into high gear in early fall. September marks the unofficial start of “art season,” when galleries within the Sarasota Art Museum offer up fresh exhibitions and new performances take the stage at the Asolo Repertory Theatre or the Sarasota Opera. And of course, the world-renowned Art of Performance at The Ringling arrives in October, bringing dazzling dance, theater, and music from around the globe. It’s the perfect blend of sun-soaked days and inspired evenings that only Sarasota can deliver this time of year.

• Where to Stay in Sarasota: Cirque St. Armands Beachside | Lido Beach Resort | The Resort at Longboat Key Club | Zota Beach Resort

CADILLAC MOUNTAIN IN BAR HARBOR IS CALLING

Bar Harbor’s Acadia National Park is a must-visit any time of year, but in fall, it takes on a whole new character. September and October bring cooler temps, vibrant foliage, and – starting October 27, 2025 – a break from the usual vehicle reservation system required to drive up Cadillac Mountain for sunrise (If you’re not familiar with the process, you can learn about it in our blog post “How to Navigate Acadia National Park’s Vehicle Reservations System.”) After this point, that means it’s just you, the crisp coastal air, and some of the most breathtaking views in the Northeast. Time it just right, and you might just have nature’s grandest show all to yourself.

• Where to Stay in Bar Harbor: West Street Hotel | Harborside Hotel, Spa & Marina

TWO WORDS: FANTASY FEST IN KEY WEST

If you know, you know. If you don’t – well, get ready. Fantasy Fest in Key West is a wild, week-long celebration at the end of October (October 17–26 in 2025) that turns the island into one big, costumed street party (think Mardi Gras, but with more body paint). It’s the ultimate mix of creativity, freedom, and fun, featuring everything from dazzling masquerade balls and themed parties to quirky contests and electrifying live performances. Whether you’re a first-timer or a seasoned reveler, Fantasy Fest is a one-of-a-kind experience you won’t forget.

• Where to Stay in Key West: The Capitana Key West | The Laureate Key West | Opal Key Resort & Marina | Sunset Key Cottages 

LAKE GEORGE’S UNDERRATED HIKING SEASON

September may not flaunt the full blaze of autumn color just yet, but it rewards hikers with something just as special: clarity, stillness, and uninterrupted time with the landscape. Popular trails like Buck Mountain, Sleeping Beauty, and Shelving Rock are drier and easier to navigate, the late-summer haze lifts to reveal crystal-clear views across the lake and Adirondack peaks, and it’s also the tail end of “bug season,” meaning fewer mosquitoes and blackflies to swat at while you climb. Add to that quieter trailheads and peaceful summit picnics, and you’ve got a hiking experience that feels like a well-kept local secret.

• Where to Stay in Lake George: The Sagamore Resort

DELRAY BEACH RESTAURANT MONTH IS A HIDDEN GEM

Foodies, take note: All of September is Restaurant Month in Delray Beach, when more than 40 restaurants, cafés, and fast-casual eateries roll out exclusive deals – from multi-course prix fixe lunch and dinner menus to happy hour specials, café perks, and culinary events. It’s a delicious way to experience the town’s vibrant dining scene at a fraction of the price, with standout spots like 50 Ocean and Drift among the participating restaurants. Add in sun-soaked days spent on Florida’s number-one beach, and you’ve got the ultimate indulgent escape.

• Where to Stay in Delray Beach: The Atlantic Suites on The Ave | Delray Sands Resort | Opal Grand Resort & Spa