5 Unbeatable Spots for a Fall Family Trip

Foliage, festivals, and fun!

If you think family vacations are only for summer, you’re missing out—on the fall fun, that is. With cooler weather, cozy seasonal activities, and gorgeous foliage, autumn is the perfect time to visit a new city. Plus, a fall family trip gives everyone the chance to connect, explore, and make unforgettable memories.

Ready for an autumn adventure? Pack the matching family flannels and start planning a getaway to one of these perfectly fall-flavored destinations.

• Burlington, VT

  Kid-friendly fall vibes!

  With its mix of outdoor activities and seasonal charm, laid-back Burlington is a family favorite in the fall. And it’s an absolute must for foliage lovers! Perched on the shores of Lake Champlain, the entire city bursts into gold, orange, and fiery red each autumn. For the most amazing lakefront views, take a leisurely walk or bike ride along the Burlington Bike Path.

  Downtown, pedestrian-friendly Church Street Marketplace makes exploring easy. Watch the street performers, then retreat to one of the cozy cafes for hot chocolate and maple-flavored treats. And just outside of town, you’ll find apple orchards, pumpkin patches, hayrides, and more fall fun for all.

  Best fall family trip for: leaf peeping and fresh-air fun

• Chicago, IL

  Big-city fall energy!

  If you’re looking for an action-packed autumn getaway, Chicago definitely delivers. And the fall flair makes it even better. Take a family stroll along Lake Michigan, where the vibrant trees paint the skyline. Then snap a family photo in front of the iconic “Bean,” perfectly reflecting the season’s colors. And over in Lincoln Park, you’ll find pumpkin patches, farmers’ markets, and leafy views.

  When the wind picks up (this is Chicago, after all!), head indoors for world-class attractions. Kids of all ages will love exploring the Field Museum, watching aquatic life at the Shedd Aquarium, and stargazing at the Adler Planetarium.

  Best fall family trip for: City adventures with a seasonal twist

• New York City, NY

  Autumn adventures for the whole crew!

  Let’s be real, you guys: no city does fall magic quite like the Big Apple. Central Park is the picture-perfect spot for leaf-peeping, with its winding paths and dazzling trees. And the Bronx Zoo and New York Botanical Gardens add seasonal fun with festivals, pumpkin displays, and colorful foliage walks.

  More family fun awaits in the heart of Manhattan. Times Square is a classic, any time of day or night. Nearby Broadway matinees are perfect for younger audiences. Want a fall twist? Hop on a harbor cruise to see the Statue of Liberty framed by crisp autumn skies.

  Best fall family trip for: Iconic sightseeing with fall flavor

• Orlando, FL

  Spooky season at the theme parks!

  Who says fall fun has to equal chilly weather? O-town brings all of the autumn excitement, plus a dose of sunshine. The city’s world-famous theme parks go all out this time of the year, with both Halloween decor and fall-themed fun. Top pick: Mickey’s Not-So-Scary Halloween Party, with trick-or-treating throughout the park and family-friendly festivities for little ones.

  Beyond the parks, Orlando is packed with ways to celebrate the fall. Local pumpkin patches, corn mazes, haunted forests, and hayrides pop up across the city. And with the cooler weather, seasonal festivals and outdoor movie nights make their return, adding to the autumn fun.

  Best fall family trip for: theme park magic with a seasonal flair

• Salem, MA

  Where history meets mystery!

  With its witch trial history, Salem is hands-down the ultimate destination for fall’s spookiest vibes. The whole city leans into its famous past, with festivities that range from fairly frightening to positively playful. Haunted Happenings runs throughout October, with parades, costume parties, and other special events. Meanwhile, Halloween lovers of all ages will be “enchanted” by the locations seen in the beloved Hocus Pocus films.

  Families with younger children can explore the Salem Witch Museum or a Salem Kids Tour for a mix of history and lighthearted spookiness. Or amp up the fall vibes with a harbor cruise and stunning foliage views of the coastline.

  Best fall family trip for: Halloween thrills plus historic charm

A fall family trip to one of these cities brings the perfect blend of colorful leaves, festive fun, and plenty of memories waiting to be made.

And to make sure your trip is all treats, no tricks, ship your bags to your final destination with LugLess. No hauling heavy bags through the airport, no wasting time at baggage claim. Just you, the fam, and more time for cider, costumes, and leaf-peeping adventures.