Where to Spend a Long Weekend in the Southeast This Fall

Bavarian village; Helen, Georgia | Shutterstock
Bavarian village; Helen, Georgia | Shutterstock

Your hair survived the three months of humidity that was Summer 2019, and now fall has arrived as a breath of fresh air -- literally. Fall is an interesting time of year in the southeastern US (in a good way) because half of the region gets the changing leaves and fall temperatures the season is known for internationally, and the other half just gets… less hot. (Hiii, Florida.) Either way, with so much to do in these five, very different long weekend destinations, Fall 2019 is sure to be a blast. 


Helen, Georgia
Planning a friends' weekend this fall? Make it a European adventure -- in rural Georgia. Yes, tucked away in the state’s northeast corner, pint-sized Helen (it’s just 2.1 square miles in size) is a real-life Bavarian village right in the heart of the Blue Ridge Mountains. In the town center, the  buildings appear straight out of a German fairytale; think steeply pitched roofs, quaint cross gables, and colorful half-timbering. Not surprisingly, Oktoberfest is a major draw here, attracting thousands of locals and travelers every fall. 

When you’re finished eating bratwurst at The Troll Tavern and shouting “prost!” with steins of Hefeweizen in hand, this mountain town has plenty else to do. Hike the Anna Ruby Falls Trail to twin cascading waterfalls; go tubing down the Chattahoochee River; or attempt zip-lining, a high ropes course, or a 50-foot swing at Nacoochee Adventures. If history is your thing, dig up Georgia’s Cherokee roots at the Sautee Nacoochee Indian Mound or relive the Gold Rush by panning for gold and gems at Dukes Creek Gold and Ruby Mine. Most notably (outside of the German thing, of course), Helen is actually surrounded by wine country. Call a car and spend the cool fall day vineyard hopping from Habersham Vineyards and Winery to Yonah Mountain Vineyards to Kaya Vineyard and Winery and more. 

Where to stay: The Valhalla Resort Hotel (from $299/weekend night) is always a safe bet, but to get the most for your money, consider renting a mountain house on Airbnb. Depending on the size of your group, you can snag an entire home for less than $200/night and find options with wraparound porches, full kitchens, hot tubs, fireplaces, and more. 

Duval Street; Key West, Florida | Shutterstock


Key West, Florida
Key West is always a good idea -- but it’s an even better idea in the fall, when you’re free from the summer’s humidity, winter’s snowbirds, and spring’s spring breakers. Plus, that’s when the 40th edition of the Keys’ famous no-boundaries street party, Fantasy Fest, comes to town. When you visit, do as the locals do: Relax. The only thing you should ever stress over in the Florida Keys is where you’re getting your next mojito, and even that’s not worth worrying about, since you’re never more than 10 feet from one and they’re always delicious. Spend your days on the water whether you’re swimming, paddle boarding, scuba diving, renting jet skis from Barefoot Billy’s, partying on a floating Tiki hut with Cruisin’ Tikis, or touring a coral reef on a glass-bottom boat ride with Fury Water Adventures. If you love to read or write, follow the spirit of Ernest Hemingway to the Hemingway Home & Museum and learn about the famed author’s life. 

It goes without saying that Duval Street is a must; drink anything at Sloppy Joe’s, specialty shots at Irish Kevin’s, or a 190 Octane at Fat Tuesday, then take a break at the myriad of eclectic shops and art galleries lining Duval. You’ll need some food, so start your day with breakfast at Blue Heaven, get tacos at the Garbo’s Grill food truck, go to Matt’s Stock Island (at The Perry Hotel) for crab beignets, and savor a slice of the area’s famous Key lime pie at Kermit’s. Wherever you are at sunset, stop what you’re doing and head to Mallory Square, where every night the locals celebrate the sunset among vendors, street performers, fire dancers, and more. 

Where to stay: Located on Stock Island, The Perry Hotel is a spacious and sophisticated, yet affordable (weekend rooms start as low as $237/night) hotel that’s close enough to Duval Street to take advantage of all its nightlife, but far enough away to feel like you’ve found your own personal retreat. 

Blue Ridge Mountains; Greenville, South Carolina | Shutterstock


Greenville, South Carolina
Located in the northwestern corner of South Carolina, at the foothills of the Blue Ridge Mountains, Greenville finds the perfect balance between sophisticated city living and the great outdoors. In this charming city, spend your days hiking the four-mile Raven Cliff Falls Trail in Caesars Head State Park (it ends at 420-foot waterfall), shopping down Main Street, exploring Falls Park on the Reedy from the suspension bridge dangling above it, or riding a bike along the 22-mile Swamp Rabbit Trail from Greenville to neighboring Travelers Rest. If you’re into sports, catch a minor-league Greenville Drive game at Fluor Field. Once dusk hits over the peaks, it’s time to make your way to one of the city’s rooftop bars (Sip Whiskey & Wine is a local favorite). 

At night, eat dinner at James Beard Award-nominated The Anchorage, see whatever Broadway show is in town at the Peace Center, try the award-winning dunkel at Yee-Haw Brewing Co., or head back to Main Street and bar hop from Crafted at Nose Dive to Vault & Vator under the road’s twinkling white lights. Greenville is definitely a festival town, and in addition to weekly farmers markets and art fairs taking over downtown, every October, the annual Fall For Greenville hosts booths from 40-plus local restaurants and seven stages showcasing more than 75 bands. If you can spare an hour, hop over to Furman University to walk around its lake, wander its idyllic rose garden, and, of course, visit the iconic bell tower. Be careful who you take to the tower, though. According to legend, whomever you kiss under there… you marry.  

Where to stay:Aloft Greenville Downtown is clean, minimalist, and trendy with a nice pool and a full fitness center. The hotel puts you in the best possible location (just steps from Falls Park on the Reedy) and weekend rooms start around $250/night. 

Palm Beach, Florida | Shutterstock


The Palm Beaches, Florida
Made up of 39 towns and cities, there’s literally a place for everyone in The Palm Beaches. No really, we mean it. Want to live your best bougie life? Palm Beach or Boca Raton. Want to hang out with all the cool kids? Delray Beach. Want to be as far as possible from anything the kids are calling “cool"? Jupiter. And the list goes on and on. 
Just like its cities, there are dining options and activities for every type of traveler, too. Don’t miss the pimento cheese made table-side from the James Beard Award-nominated chef at The Regional in West Palm Beach; or the pu pu platter at Hai House, a glamorous Chinese restaurant hidden behind the Gucci store on Worth Avenue in Palm Beach. Step back in time with cocktails at HMF at The Breakers. Taste the best of downtown Delray Beach with a three-course, progressive dinner led by the fun guys over at Craft Food Tours; it includes a cocktail and dinner course at three different restaurants for just $79 per person. 

With 47 miles of golden-sand beaches, the Atlantic Ocean is always just within reach. Rent a boat for the day and sail past the mansions on “Billionaires Row.” Go snorkeling in one of more than 100 artificial reefs. Take a kayak or a paddle board out on the Intracoastal Waterway. For something on dry land, test your golf skills at one of 160 courses. If it’s culture you seek, visit the Norton Museum of Art, go to an authentic Japanese tea ceremony at the Morikami Museum and Japanese Gardens and tour its 16 acres, or take a $10 walking tour of Worth Avenue with historian Rick Rose. Speaking of Worth Avenue, if you’re into high-end shopping (or -- who are we kidding -- people-watching), there’s no place like it. Running through the heart of tropical-chic Palm Beach, the street is an oasis of haute designer storefronts (it’s home to the Lilly Pulitzer flagship), hidden courtyard cafés, and celebrity shoppers. Tired of shopping? Hit the beach; it’s where Worth Avenue ends. Like we said, there’s truly something for everyone.  

Where to stay:The Colony Hotel -- where walls and floors are covered in palm-leaf wallpaper and carpeting, rooms have cotton-candy pink accents, and there’s a weekly jazz brunch by the pool -- is everything you picture when you think of preppy Palm Beach. Located just a block from Worth Avenue, the salmon-pink building is an iconic part of the skyline, but you can still get a weekend room there for as low as $239/night in early fall.

The Fort of Colonial Mobile; Mobile, Alabama | Shutterstock


Mobile, Alabama
Mobile is the port city weekend you didn’t know you needed. Sitting right on the Gulf of Mexico, it's packed with a mix of French, Spanish, and American influences and its streets, shaded by towering oak tree canopies and historic Old South mansions, appear straight out of Gone With the Wind. While there, visit the “Mighty A” battleship, walk through the city’s historic and arts districts, and explore The Fort of Colonial Mobile, a French colonial post built in 1723. Surprising to many, the oldest Mardi Gras celebration in the country isn’t in New Orleans -- it’s in Mobile. For that reason, make sure you check out the Mobile Carnival Museum, which documents the city’s Mardi Gras traditions from the day it all began. When you get hungry, try the local specialties: get Gulf shrimp and grits at The Noble South, barbecue sandwiches at Meat Boss, and a board of Alabama-made cheeses at The Cheese Cottage.

If you like the outdoors, go camping on Dauphin Island or explore Mobile’s acres of scenic waterways, woods, wetlands, and parks; it’s the reason this part of the country is called “America’s Amazon.” Five rivers meet here -- the Mobile, Spanish, Tensaw, Apalachee, and Blakeley -- so there are plenty of places for kayaking, nature walks, and paddle boarding. Fall brings a series of festivals to Mobile; in October, the weekly Park After Dark will offer family-friendly fun every Sunday, and the first weekend of November, the third annual Wine on the River Mobile and the Alabama Pecan Festival both return.

Where to stay: The Battle House Renaissance Mobile Hotel & Spa is located downtown and has a high-end Southern restaurant, tavern, heated rooftop pool, spa, tennis court, and fitness center. Standard rooms are decorated in a traditional Southern style and start at $170/weekend night in the fall.