Under 2 Hours: Westchester, NY/Fairfield, CT Counties
Stay: Inn at GrayBarns, Bedford Post Inn, Roundhouse
Eat: Inn at Pound Ridge, Blue Hill; restaurants at Graybarns, Bedford Post Inn, and Roundhouse.
Do: Hike in Rockefeller State Park Reserve or Devil’s Den Preserve; visit the farm animals at Stone Barns, get your art+nature fixes at Storm King Art Center, Dia: Beacon, The Glasshouse, Grace Farms, Untermyer Park and Gardens.
Under 3 Hours: Hudson, NY
Stay: WM Farmer & Sons, Rivertown Lodge, Collective Retreat Tents
Eat: In town: Fish & Game, Aeble, Back Bar, Oak Pizzeria, Grazin’ Diner, Hudson Food Studio, Moto Coffee; provisions at Talbot & Arding and Olde Hudson Market; a bit further out is Gaskins, Bonfiglio & Bread, Brunette Wine Bar, and Bartlett House.
Do: shop along Warren Street (the main drag in town) lined with high-end home décor and antique stores – favorites include Rural Residence, Finch, Hawkins, Red Chair, Les Indiennes. Some cool clothing and accessories stores include Mutiny, Sideshow Vintage, Bavier Brook. Head over to High Falls Conservation Area for a quick yet scenic hike, or walk the grounds of the Art Omi where architecture meet nature in the fields.
Under 3 Hours: The Catskills
Stay: Foxfire Mountain House, Audrey’s Farmhouse, Scribner’s Lodge, Deer Mountain Inn, Woodstock Way
Eat: Westwind Orchard Pizza, The Greenhouse at Audrey’s, Bar Room at Foxfire, Prospect at Scribner’s, Dining Room at Deer Mountain, Shindig in Woodstock, Phoenicia Diner.
Do: go apple-picking at Fishkill Farms, picnic along the cliffs in Minnewaska State Park, hike to Kaaterskill Falls, ski/snowboard Hunter Mountain, stroll through Woodstock, vintage clothes-hunting at the massive second-hand shop in Tannersville.
Under 4 Hours: Delaware River Valley/Poconos
Stay: The DeBruce, Nine River Road, The Arnold House, North Branch Inn; Brushland Eating House and Table on Ten have rooms to rent
Eat: The DeBruce and Brushland Eating House are well-known for culinary excellence, while the pubs at The Arnold House and Table on Ten are great for a casual meal. The Heron in Narrowsburg is excellent, a bit further down the river.
Do: horse riding at Bridle Hill Farm, visit the adorable Buck Brook Alpacas, drinking at Wayside Cider Taproom, snowshoeing at The DeBruce, fly-fishing is also popular along the river.
Under 4 Hours: The Berkshires
Stay: Tourists
Eat: The Prairie Whale, Lodge Bar at Tourists. Bright Ideas Brewery, Widow Bingham’s Tavern at Red Lion Inn; provisions at Wild Oats Market and Cricket Creek Farm.
Do: if you’re into contemporary art, explore the huge MassMOCA complex, or go classic at The Clark Institute for high design by Tadao Ando housing a impressive collection of old masters; hike the many trails at Mt. Greylock.
