We like these places. We really, really do.
By Isabel Hochman
Copake Country Club
44 Golf Course Road, Craryville, NY 12521
This public 18-hole course on Copake Lake designed by architect Devereux Emmet offers dining, walks and water sports.
Hotchkiss Golf Course
48 Interlaken Road, Lakeville, CT 06039
Designed in 1924 by architect Seth Raynor, this nine-hole course offers views of Lake Wononscopomuc.
Berkshire Hills Country Club
500 Benedict Road, Pittsfield, MA 01201
This century old Berkshires favorite was designed by architect A.W. Tillinghast.
Wyndhurst Golf & Club
55 Lee Road, Lenox MA 01240
This historic 18-hole golf course offers breathtaking views of the rolling Berkshire Hills and a fitness club.
103 Laurel House Road, Haines Falls, NY 12436
This legendary waterfall hike drops in two tiers, more than 260 feet from top to base.
Roeliff Jansen Park
116 Old Route 22, Hillsdale, NY 12529
This scenic spot has a great dog run and farmer’s market.
Mass Audubon’s Lime Kiln Farm Wildlife Sanctuary
113 Silver Street, Sheffield, MA 01257
For spectacular views of the Taconic Mountains and Berkshire Hills choose the 1.25-hour hiking option.
Mass Audubon’s Pleasant Valley Wildlife Sanctuary
472 West Mountain Road, Lenox, MA 01240
Trail of the Ledges is where you’ll find amazing views of Lenox Mountain, Mount Greylock, the Taconic Range and the Catskill Mountains.
Sweet William’s Coffee Shop & Bakery
17 Main Street, Salisbury, CT 06068
Treat yourself to an afternoon cupcake with coffee from Barrington Coffee Roasting Company and milk from
High Lawn Farm. Yum.
Mansion + Reed General Store
45 Reed Street, Coxsackie, NY 12051
Twin sisters Lisa and Justine Post source goods locally from NY state businesses and they have an amazing cappuccino.
The Southfield Store
163 Norfolk Road, Southfield, MA 01259
The perfect Sunday brunch, with delicious coffee—try the Shirl’s Granola bowl, it’s the best!
Cook & Larder
2642 NY-23, Hillsdale, NY 12529
Closed on Monday and Tuesday, this is the perfect weekend go-to spot to sit and catch up with old friends and new, or grab some chicken parmigiana for takeaway.
517 Warren Street, Hudson 12534
This family-friendly spot specializes in wood-fired pies with sourdough crust and gourmet toppings, with an exceptional gluten-free option.
84 Main Street, Lenox, MA 01240
Owners Molly, David and Roman always offer amazing date night specials (just ask).
18 Main Street, Millerton, NY 12546
This cash-only institution has been a mainstay for my whole life. As a kid, Friday night drives up to Great Barrington from Manhattan meant a stop in Millerton for pizza, meatball subs and ravioli.
3279 Franklin Avenue, Millbrook, NY 12545
Neapolitan-style pizzas fresh out of the pizzaiolo and crafted cocktails in a warm, intimate setting.