There’s nothing quite like fall in the U.S. — crisp air, cozy sweaters, pumpkin spice everything, and of course, those spectacular bursts of red, orange, and gold leaves. If you’ve been itching for a scenic drive or weekend getaway, this is the perfect season to hit the road.
Whether you’re flying cross-country or starting your adventure closer to home, we’ve rounded up the best fall foliage road trips — and where to leave your car before you take off from major airports like Boston (BOS), Chicago (ORD), Washington, D.C. (DCA), and San Francisco (SFO).
1. Boston Logan International Airport (BOS) — Classic New England Charm
New England is the gold standard for fall foliage. Think winding roads through covered bridges, colonial villages, and apple orchards that smell like cider doughnuts.
Top Fall Foliage Road Trips from Boston
- The Kancamagus Highway (New Hampshire): This 34-mile scenic byway runs through the White Mountains, with panoramic views that look straight out of a postcard. Peak color typically hits late September to mid-October.
- Mohawk Trail (Massachusetts): One of the oldest scenic routes in the U.S., lined with craft shops, farm stands, and sweeping mountain vistas.
- Cape Ann & Rockport: Coastal drives aren’t just for summer — fall brings fewer crowds and stunning foliage along the Atlantic.
Travel Tip:
If you’re flying out of Boston Logan International Airport, On Air Parking offers affordable off-site parking so you can skip the airport chaos and save your budget for maple syrup souvenirs.
2. Chicago O’Hare International Airport (ORD) — Midwest Colors and Lake Views
The Midwest knows how to put on a fall show — blazing reds, golden oaks, and peaceful drives through rolling countryside.
Top Fall Foliage Road Trips from Chicago
- Great River Road (Illinois): Follow the Mississippi River from Galena to Grafton for small towns, bluffs, and endless river views.
- Starved Rock State Park: Just 90 minutes southwest of Chicago, this park is famous for its sandstone canyons and vibrant foliage trails.
- Door County, Wisconsin: A 4-hour drive from Chicago — think lighthouses, orchards, and fiery maples reflected in Lake Michigan.
Travel Tip:
Leaving your car at O’Hare International Airport for a fall flight? Book On Air Parking to save on long-term parking and make sure you have extra cash for apple pie and roadside coffee stops.
3. Washington Reagan National Airport (DCA) — Autumn in the Capital Region
Fall is arguably the prettiest time to visit Washington, D.C. The city’s monuments glow against a backdrop of changing leaves, and just a short drive away, you’ll find some of the East Coast’s most underrated fall road trips.
Top Fall Foliage Road Trips from D.C.
- Shenandoah National Park (Virginia): Only 75 miles from D.C., the Skyline Drive winds through 105 miles of jaw-dropping mountain scenery. The colors usually peak in mid to late October.
- Harpers Ferry (West Virginia): A charming historic town where the Potomac and Shenandoah Rivers meet, surrounded by hiking trails and scenic overlooks.
- Annapolis, Maryland: A coastal twist on fall travel — stroll historic streets lined with amber leaves, then grab crab cakes by the water.
Travel Tip:
If you’re flying from DCA, leave your car with On Air Parking’s off-site partners nearby. You’ll save money and time navigating one of the busiest airports on the East Coast.
4. San Francisco International Airport (SFO) — California’s Golden Season
California might be known for its beaches, but fall brings its own kind of magic — harvest festivals, vineyards, and forests painted in golden light.
Top Fall Foliage Road Trips from San Francisco
- Napa Valley: Beyond the wine, you’ll find rows of vineyards that turn brilliant gold and crimson in October.
- Lake Tahoe: The drive along Highway 50 offers alpine views, hiking trails, and dazzling aspen groves.
- Big Sur: While it’s known for coastal cliffs, the redwoods along Highway 1 glow a deep orange under the fall sun.
Travel Tip:
Flying out of SFO for a leaf-peeping adventure? Book with On Air Parking for the best off-site parking near the airport — secure, affordable, and just minutes away.
Fall Road Trip Essentials
- Layered clothing: Mornings and evenings can get chilly — especially in the mountains.
- Camera or smartphone: You’ll want to capture those fiery maples and sunset drives.
- Snacks & hot drinks: Apple cider, trail mix, and a thermos of coffee make every road trip better.
- Playlist: You can’t go wrong with some Fleetwood Mac, The Lumineers, or classic road trip rock.
On Air Parking’s Fall Travel Tip
If your fall foliage plans include flying to meet friends or explore a new region, On Air Parking makes it easy (and affordable) to leave your car behind. With secure, off-site lots near BOS, ORD, DCA, and SFO, you’ll save big — and spend more on cozy sweaters, cider tastings, or that scenic detour you just have to take.
Ready to Chase the Colors?
From New England’s fiery forests to California’s golden vineyards, the best way to experience fall is behind the wheel — and On Air Parking helps you get there with affordable airport parking in every season.
So grab your keys, roll down the windows, and let autumn’s magic lead the way.