The itsy-bitsy village of Millbrook is one of upstate New York's finest. Stately homes, rolling Hudson hills and tree-lined sidewalks offer an all-American vibe for a long weekend. Start at Babette's Kitchen where a breakfast of lemon cookies (that's healthy, right?) awaits, then take yourself to Millbrook Yoga for a self-care session. The local farmer's market is legendary. Browse over 20 stalls for lunchtime nibbles, then head to Franklin Avenue for a spot of small town shopping in the indie stores of the village's main street. In the evening, we'll meet you at the bar at Canoe Hill, for sweet, plump East Coast oysters on ice.

There's no better time to experience an Ivy-League campus than in autumn's burnished weeks. Dartmouth College students flock to Hanover's bars and restaurants after lengthy football practices to refuel, and there's no better place to get in the back-to-school spirit than this elegant university town. We'd skip trips to J.Crew and cocktails at the Hanover Inn (popular with visiting parents), and take advantage of the myriad hiking and running trails in the area. Feeling adventurous? Try your hand at canoeing on the Connecticut River.

Where to stay: The Norwich Inn

Looking for an autumnal alternative to the Hamptons? We've got you. Long Island's North Fork offers plenty more uncharted territory to explore than its southern counterpart. This is swaddling yourself in wooly layers, and gaze out across crashing waves from a quiet cottage window, Taylor Swift's folklore playing quietly in the background kind of country. Prepare for blustery beachside strolls and an abundance of visits to farm-to-table restaurants. Our favourite is the North Fork Table and Inn. This stretch of Long Island is also home to a number of wineries, so we'd recommend booking in an afternoon of rosé tasting at Croteaux Vineyards.

Where to stay: Sound View

Surrounded by rolling hills and bucolic pastures dotted with firetruck-red barns, Woodstock is a New England dream come true. Hiking is a rite of passage when autumn arrives in the surrounding mountains, so we'd recommend packing your boots, so you can zig-zag your way beneath the changing leaves, breathing in the crisp, clear air before returning to the Big Apple. For serious farm-to-table fare, check out the rustic Cloudland Farm, where the fresh tomato soup with grilled cheese and basil oil along with braised pork with crabapple compote compel visitors to return time and time again.

Where to stay: Hotel Dylan

Bordering the Hudson River, this picturesque town some 115 miles from NY has become something of an executive hangout for the city's suits, but don't let that put you off. There's a reason they're switching jackets for joggers and heading here on the weekends. Long cited as a inspirational hangout for writers and painters, Hudson's latest generation of live-in creatives are intent on keeping its smartly painted streets humming with craft and culture. Head to Warren Street to meet some of its most successful makers, like the team behind handmade home goods studio, Minna. Food, too, is in the spotlight right now. Try David Chicane's Food Studio Hudson or the Rivertown Lodge's Tavern for platefuls of grilled pork ribs glazed with an umeboshi glaze, scallops swimming in a parsnip buttermilk and blushing duck served with a sharp mustard jus.

Where to stay: Wm. Farmer and Sons

There are two ways to do the Catskills. The first option is to round up a group of friends and rent a house by the water, with lake views, leaf-peeping opportunities aplenty and a utility room to store muddy boots and wet coats in. The second? To head into seclusion and book a night in a forest-cocooned tiny cabin tucked between the Catskills peaks and Berkshire's beauty. We're opting for the second one if it means a night at under pine in one of Gather Greene's scandi-cool cabins. Hole up for the weekend, take time to meander under the cherry red leaves of the surrounding woods towards a hidden lake, watch the sunset over the mountains and, if you're wanting some human interaction, head to the campfire for s'mores and stories come nightfall. With 17 sweet huts to pick from, you could even take your friends.

Where to stay: Gather Greene