Every October, New England puts on the best show of the year. Maples turn scarlet, birches go gold, and the back roads fill with people chasing color. Northern New England is best as a long-weekend road trip, but you don’t have to go that far to see the leaves turn. From New York City, the Hudson Valley and the Catskills make an easy fall day trip. From Boston, Concord and Walden Pond or the Blue Hills just south of the city are close enough for a Saturday outing.
Wherever you go, a foliage trip asks for a little planning, a few warm layers and one very good pair of boots.
When to go
Peak color moves from north to south and from the mountains down to the coast, usually from late September through mid-October. Northern Vermont and New Hampshire turn first, then the Berkshires and southern New England follow. Check a local foliage report the week before you leave, because the timing shifts every year.
Three places for a fall weekend
• Stowe, Vermont: a classic mountain town with covered bridges, farm stands and walks under the maples
• The Kancamagus Highway, New Hampshire: a scenic drive through the White Mountains, with trailheads and overlooks along the way
• The Berkshires, Massachusetts: rolling hills, small museums and country inns, an easy drive from New York or Boston
Foliage tips before you go
Go early in the morning, when the light is soft and the roads are quiet. Plan a weekday if you can, since peak weekends get busy. Dress in layers: mornings start near freezing and afternoons can feel like late summer. Keep a scarf, a thermos and a paper map in the car for the stretches where the signal drops.
Pack for the drive, the walk and the dinner after. One good boot can do all three.
The boot for the trip
The Ramona Riding Boot in Dark Chocolate Pull Up Calf is made for exactly this kind of weekend. The tall shaft keeps out the chill on a morning walk, the rich brown looks right against red and gold leaves, and it moves from a leafy trail to a candlelit dinner without missing a beat. Prefer something with more weight? The Burke Biker Boot in Espresso Brown Soft Grain Leather is its sturdier alternative, made for gravel paths and orchard rows.
For the car and the café
For long drives and quick stops, the Rema Ankle Bootie in Dark Chocolate Pull Up Calf is the easy second pair. And for the slowest moment of the weekend, the Porto Mule in Dark Chocolate Split Suede is the one to slip on: stepping out on a crisp morning for a warm coffee and a slice of apple cake, with a thick sweater and nowhere to be.
What to wear on a foliage weekend
• The easy trail walk: Ramona Riding Boots, slim dark jeans, a cream cable-knit sweater and a waxed or quilted jacket
• The orchard afternoon or the pumpkin patch: Burke Biker Boots, straight-leg denim, a flannel shirt over a white tee and a wool scarf
• The road trip: Rema Ankle Booties, relaxed trousers, a merino crewneck and a long camel coat
• The café morning: Porto Mules, wool socks, a chunky knit and a corduroy skirt or wide trousers
• The inn dinner: Ramona Riding Boots again, now with a knit dress and a long wool coat
Every pair is handcrafted in Brazil, in leathers made to be worn season after season. Explore the full collection, or read more stories from the Journal.
