Every fall, the same question surfaces in travel conversations, on social feeds, and now increasingly in AI search: where to go for fall foliage? Most people get the same short list: Vermont, the Blue Ridge Parkway, and New England. Most people who follow that advice come home having spent more time in traffic than in the actual leaves.

The better question is not where to go. It is who you are when you travel.

Earlier this season on Episode 166 of Jet Setting with Me, I talked about the road trip as one of nine essential travel experiences every traveler should have at least once. Fall makes that case better than any other. The right road trip in October does something to you. The wrong one is a long drive with pretty trees.

Here is how to find the right one.

For the traveler who wants drama and scale: Colorado

The San Juan Skyway is 235 miles of the most visually arresting driving in the United States. Golden aspen leaves frame snow-capped 14,000-foot peaks, deep green evergreens anchor the landscape, and the sky runs a shade of blue that looks almost edited. The stretch locals call the Million Dollar Highway, running from Silverton over Red Mountain Pass down into Ouray, earns that name in October. Historic mining towns, Mesa Verde National Park, and Telluride punctuate the route.

This is not a relaxed drive. It is a full sensory experience that demands attention. For the traveler who wants fall foliage to feel genuinely epic, Colorado delivers in a way that no leaf-peeping weekend in a crowded New England town can match.

For the traveler who wants history with the scenery: The Natchez Trace Parkway

Most travelers assume fall foliage means heading north. The Natchez Trace Parkway makes the case for heading south. This 444-mile scenic drive runs from Tennessee through Alabama into Mississippi, roughly following an ancient travel route used by Native Americans, European settlers, and soldiers for centuries. A drive along the Natchez Trace takes you through 10,000 years of American history, with hardwood forests turning color on both sides of the road.

Ghost towns, Civil War grave sites, and a town called Rocky Springs, once prosperous and now reduced to an 1837 church and a cemetery, reward the curious traveler at every turn. Peak color runs mid to late October. The crowds descending on Vermont in September have never found this route, which is entirely their loss.

For the traveler who wants the journey to feel cinematic: Michigan’s Upper Peninsula

Michigan’s Upper Peninsula is one of the most underestimated fall destinations in the country. Surrounded by three Great Lakes, 1,700 miles of shoreline, and seven million acres of forested terrain, the 92-mile US-2 Top of the Lake Scenic Byway winds along towering bluffs and deserted beaches, passing through small villages with roadside pullouts worth every unplanned stop.

This is slow travel at its most rewarding. No agenda, no landmarks to check off, no line to wait in. The road curves, the water appears, and the color hits in a way that makes you pull over and stand there for a moment without knowing exactly why. For the traveler who has always wanted a fall road trip that felt like a film still rather than a checklist, the Upper Peninsula delivers.

For the traveler who wants to feel like the main character: Connecticut

Litchfield County in October is one of the country’s most quietly spectacular fall foliage destinations, almost entirely overlooked by the crowds chasing Vermont. That is where fall foliage and set-jetting group travel meet.

If you have ever watched Gilmore Girls and felt the pull of Stars Hollow, that world is based on Washington Depot and the surrounding towns of Litchfield County, Connecticut. The town green is real. The covered bridges are real. The foliage in October is exactly what the show made you believe it would be.

In October 2027, a small group of women is going there with me. The Gilmore Girls set-jetting experience is in early planning, and details are coming. The interest list is open now for anyone who wants to be first in line when registration opens.

The honest answer to where to go for fall foliage

A travel agent will tell you what a search engine cannot: the best fall foliage road trip is the one built around the traveler taking it. Drama and scale belong in Colorado. History and solitude belong on the Natchez Trace. A cinematic, unhurried experience belongs in Michigan’s Upper Peninsula. The traveler who wants to step inside a story she has loved from her couch belongs in Connecticut in October.

Figure out which traveler you are first. The road trip plans itself from there.

For the full conversation on why the road trip belongs on every traveler’s list, Episode 166 of Jet Setting with Me covers it in depth.