The itsy-bitsy village of Millbrook is one of upstate New York's finest. With an all-American vibe - think: stately homes and tree-lined sidewalks - it's the perfect place to get completely ensconced in over a long weekend. In the name of self-care, we recommend attending one of Millbrook Yoga's classes held in a refurbished barn, followed by a stop at the farmer's market to pick up local veg and cheese for lunch at base. In the evening, stop by Canoe Hill for oysters at the bar.

There's no better time to experience an Ivy-League campus than autumn. 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. When you're not popping into J.Crew or grabbing cocktails at the Hanover Inn (to which parents head in droves come graduation weekend), take advantage of the many hiking and running trails in the area, or try your hand at canoeing on the Connecticut River.

An autumnal alternative to the Hamptons, Long Island's North Fork offers much more uncharted territory to discover than its southern counterpart. Whether you're looking to swaddle yourself in wooly layers and look out over the crashing waves from your cottage window or want to explore the area's abundance of farm-to-table restaurants, there are few oceanfront destinations that feel so perfect for the crisper months. This stretch of Long Island is also home to a number of wineries, so make sure to plan an afternoon around rosé tasting at Croteaux Vineyards.

Surrounded by rolling hills and bucolic pastures dotted with firetruck-red barns, Woodstock is a New England dream come true. Stay at the stately Woodstock Inn & Resort, where you shouldn't miss cocktails or hot cocoa by the fire in Richardson's Tavern. The surrounding mountains are marked by zig-zagging hiking trails, so it's also the perfect location to take in the northeast's changing leaves and breathe in the crisp, clear air before returning to the city. For serious farm-to-table fare, check out 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.

Hudson may stand out in many people's minds as the artist's haven to which Dan and Jenny's mother fled in Gossip Girl, and it certainly remains a prime hideaway. True to its name, this town borders the Hudson River and it has provided inspiration to communities of writers and painters for decades. Local boutique hotel Wm. Farmer and Sons combines a touch of Soho House aesthetics with cosy countryside details such as blue-and-white floral duvets and fuzzy fur pillows. The coffee shop here is old-timey and adorable, so start your day here before popping between the town's boutiques for goodies, whether you favour gourmet ingredients or handcrafted paintbrushes.

If you're looking for an October weekend by the lake, round up a group of mates and rent a house by the water in the Catskills. Break the reflection of red leaves on the lake's glassy surface while canoeing and gaze up at the starry skies during bonfires - just make sure to leave plenty of room for reading by the fireplace and long country walks. Start each morning with home-baked granola or a piping hot country loaf from one of the many local bakeries.