Where to Go

4 Weekend Trips To Take This Fall

Get away to see colorful foliage and enjoy the best of autumn

The Vacationeer
Fall foliage and aspens along a country road

As the days shorten and the temperatures fall, you may be planning next year’s summer vacation. However, fall is a spectacular season for weekend getaways. Take a trip with a backdrop of vibrant fall foliage and tons of fall-flavored fun.

While destinations like New York are well-known leaf-peeping spots, explore these four places for a memorable weekend trip, plus autumnal things to do.

Chicago skyline in the fall 


Many sights in Chicago are iconic year-round, from Wrigley Field to the Cloud Gate sculpture (commonly called “The Bean”) at Millennium Park. However, the city transforms in the fall.

Where to see fall foliage: If you want to stay close to the city, visit Lincoln Park and head to the ponds for the best fall peeping. Grant Park, home to Buckingham Fountain, hosts colorful autumnal leaves near the Art Institute of Chicago. Or take the train to Morton Arboretum just outside of Chicago for a quiet walk or bike ride.

What to do: Enjoy plenty of fall activities, from illuminated pumpkins along Navy Pier to Fall Fest at the Lincoln Park Zoo. Heap’s Giant Pumpkin Farm offers classic pumpkin picking and hayrides just outside the city. After hours, attend a candlelit concert or take a ghost tour to peek at Chicago’s supernatural history.

What to eat: Food festivals like Oktoberfest in Chicago are still in full swing in the fall. Attend festivals focused on one type of food, such as the Great American Lobster Fest, Apple Fest and WingOut Chicago. Foodies, don’t miss the Chicago Gourmet and the Lincoln Park Wine Fest. Or experience the food and culture of different cultures as festivals celebrating Chicago’s Puerto Rican, Polish and Greek populations.

Where to stay: Sleep among the Windy City’s skyline at Chicago Magnificent Mile, a Hilton Grand Vacations Club.

Aspens along Lake Tahoe in California in their fall colors 

Lake Tahoe, California

Outdoor adventures await travelers year-round at Lake Tahoe. However, the fall transforms lakeside views with golden hues. You can still enjoy your favorite outdoor activities in autumn, plus take advantage of some seasonal amusements.

Where to see fall foliage: Hike through Hope Valley, just south of South Lake Tahoe, for trails that meander through golden aspen trees and other fall flora. The drive to Carson Pass is particularly scenic this time of year.

What to do: In October, thousands of kokanee salmon instinctively leave the lake and head upstream to spawn. Walk along the Rainbow Trail to spot spawning salmon moving up Taylor Creek and get an underwater view of the salmon at one of the stream profile stations. You may even catch sight of bears enjoying salmon — be sure to give local wildlife plenty of space.

What to eat: Savor the harvest season and support local farmers at Apple Hill, an agricultural community. At Apple Hill, explore farms where you can pick produce like apples, bakeries, wineries and flower gardens.

Where to stay: After a long day outdoors, relax at Hilton Vacation Club - Lake Tahoe Resort.

Road through the woods in autumn 

Myrtle Beach, South Carolina

If you can’t choose between trees and the seas, get the best of both in Myrtle Beach, South Carolina. Beat the heat and visit in the fall when temperatures can be warm enough to swim and sunbathe. Plus, you won’t experience the crowds and price spikes accompanying summer vacationers with off-season travel.

Where to see fall foliage: The Waccamaw National Wildlife Refuge has plenty of outdoor activities while enjoying the seasonal scenery, including hiking, fishing, camping and birding. Take a boat tour of the refuge to learn about the local wildlife and enjoy the crimson cypress trees along the Waccamaw River.

What to do: Stop by Brookgreen Gardens for even more colorful leaves and their Harvest Home Weekend Festival for pumpkin picking and scarecrow building. In true harvest season spirit, visit the L.W. Paul Living History Farm and learn about farming in the early 20th century with live demonstrations and hands-on activities.

What to eat: Autumn in Myrtle Beach is all about one food: oysters. Locals recommend eating only oysters in a month that contains the letter “r.” So fall is the perfect time to enjoy oysters. If fish isn’t your favorite food, try the Cran-errific, Thanksgiving sandwich stuffed with turkey, cheese and cranberry spread from Benjamin’s Bakery & Cafe. One Hilton Grand Vacations Owner recommends New York Prime steakhouse for sumptuous steaks and seafood.

Where to stay: Choose from three charming Hilton Grand Vacations resorts in Myrtle Beach with spectacular ocean views.

Sunset near Williamsburg, Virginia, in the fall 

Williamsburg, Virginia

Williamsburg, Virginia, is a destination full of family-friendly activities across the historic triangle of Colonial Williamsburg, Jamestown Settlement and Yorktown. Enjoy the best of “the Burg” in the fall with mild temperature and minimal crowds — with a gorgeous array of autumn leaves.

Where to see fall foliage: Colonial Williamsburg offers lots of ways to enjoy fall colors — from carriage rides to the arboretum — so visitors can imagine what it was like to leaf peep hundreds of years ago. Or take a day trip to Shenandoah National Park and cruise the Skyline Drive for stunning colors overlooking wooded valleys.

What to do: See the spookier side of Williamsburg with a haunted tour and learn about ghosts, witches and pirates who used to roam the area. For a daytime history lesson, visit Jamestown Settlement. Stop by the Jamestown Glasshouse for live demonstrations of historic glass blowing.

What to eat: Wine and dine at Williamsburg Winery, and enjoy a tasting and lunch on the outdoor patio. Or eat at Pierce’s Pitt Bar-B-Que for Virginia-style barbecue. Enjoy classic Southern food like hush puppies and pulled pork, or try from a rotating special menu with seasonal eats, such as a hearty Brunswick stew. Either way, save room for dessert, like pecan pie or lemon pound cake.

Where to stay: Enjoy autumnal views from the sweeping grounds of The Historic Powhatan, a Hilton Vacation Club.

Read “3 Fall Break Bucket Lists to Fit Your Vacation Style” for even more ways to fill a weekend trip with fall flair.

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The Vacationeer

The Vacationeer is a collective of Hilton Grand Vacations storytellers whose goal is to inspire travelers to go further. We're always on the lookout for new destinations to explore, useful travel tips, and unique ideas to help you plan the most memorable vacations possible.

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