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