Leaf Peeping Road Trips: From Maine to Virginia

September 15, 2025

Where to find the season’s best color (and cider doughnuts).

The first cold snap always makes me want to drive. Windows down, sweater sleeves pushed up, the smell of woodsmoke curling into the car. Fall doesn’t just show up on the East Coast — it sets the hillsides on fire. Reds, golds, and oranges so bright they look like they could burn your hands if you touched them.

Here are the roads worth chasing this season, plus the stops along the way that make the trip just as sweet.

Maine – Route 27 to Rangeley Lakes

The drive through western Maine feels endless in the best way. Maples and birch crowd the road, flaming red and gold. Pull over at the Height of Land overlook, where the lakes shine cobalt blue beneath the ridges.

Don’t miss: Rangeley Oktoberfest (October 4, 2025), where you can sip a local brew with the same view, or stop at Furbish Brew House & Eats for a hearty meal and a pint after the drive.

New Hampshire – The Kancamagus Highway

The “Kanc” is famous, and with good reason. It cuts straight through the White Mountains, with enough pull-offs to make your camera weep. Go early, before the traffic builds.

Don’t miss: a cider stop at Applecrest Farm Orchards in Hampton Falls, or take a break at Albany Covered Bridge for that perfect fall-framed photo.

Vermont – Route 100

If one road could define fall in New England, it’s this one. Route 100 winds past farm stands, ski towns, and those postcard-perfect covered bridges. The hillsides look stitched together in squares of scarlet, amber, and gold.

Don’t miss: fresh cider and doughnuts at Cold Hollow Cider Mill in Waterbury, or time your trip with Stowe’s Foliage Arts Festival in October (October 9-11, 2025).

Massachusetts – The Mohawk Trail

One of America’s oldest scenic byways, the Mohawk Trail threads through the Berkshires with hairpin turns and sweeping views.

Don’t miss: pumpkins piled high at Whitney’s Farm Market, or a stop at Shelburne Falls, where the Bridge of Flowers is still blooming against the fall backdrop.

New York – Catskills Loop

The Catskills burn with color in October. Drive Route 28 through Phoenicia and Margaretville, then loop back on 214.

Don’t miss: a stop at Phoenicia Diner (retro comfort food with mountain views), or the Woodstock Film Festival if your trip falls in mid-October.

Pennsylvania – Route 6 Across the Northern Tier

Quieter than New England but no less stunning, Route 6 cuts through the Pennsylvania Wilds. The Grand Canyon of Pennsylvania (Pine Creek Gorge) is a must-see, rimmed with flame-colored hardwoods.

Don’t miss: Wellsboro’s Fall Festival in September or a stay at the historic Penn Wells Hotel, lit with a warm autumn glow.

Virginia – Skyline Drive

There’s no better finale. Skyline Drive rolls along the Blue Ridge through Shenandoah National Park, offering 75 overlooks in just over 100 miles. By early October, the ridges glow gold and crimson, and the sunsets are almost too much to take in.

Don’t miss: apple pie at Graves Mountain Farm & Lodges, or plan for the Shenandoah Fall Foliage Festival in nearby Waynesboro.

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The takeaway: Fall isn’t just a season here — it’s a road trip stitched together with color, cider, and the kind of light that makes you want to stay outside until the stars come out.