Golf

Copake Country Club

44 Golf Course Road, Craryville, NY 12521
518.325.0019
CopakeCountryClub.com

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
860.435.4400
Hotchkiss.org

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
413.447.9429
BerkshireHillsCC.com

This century old Berkshires favorite was designed by architect A.W. Tillinghast.

Wyndhurst Golf & Club

55 Lee Road, Lenox MA 01240
413.637.1364
WyndhurstGolfAndClub.com

This historic 18-hole golf course offers breathtaking views of the rolling Berkshire Hills and a fitness club.

Hiking

Kaaterskill Falls

103 Laurel House Road, Haines Falls, NY 12436
CatskillsVisitorCenter.org/kaaterskill

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
518.325.5073
HillsdaleNY.com/trails

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
413.637.0320
MassAudubon.org/limekiln

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
413.637.0320
MassAudubon.org/pleasantvalley

Trail of the Ledges is where you’ll find amazing views of Lenox Mountain, Mount Greylock, the Taconic Range and the Catskill Mountains.

Coffeehouses

Sweet William’s Coffee Shop & Bakery

17 Main Street, Salisbury, CT 06068
860.435.3005
Sweet-Williams.com

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
518.731.7200
MansionReed.com

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
413.229.5050
SouthfieldStore.com

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
518.325.0220
CookandLarder.com

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.

Pizza

Baba Louie’s

517 Warren Street, Hudson 12534
518.751.2155
BabaLouiesPizza.com

This family-friendly spot specializes in wood-fired pies with sourdough crust and gourmet toppings, with an exceptional gluten-free option.

Pizzeria Boema

84 Main Street, Lenox, MA 01240
413.881.4936
PizzeriaBoema.com

Owners Molly, David and Roman always offer amazing date night specials (just ask).

Taro’s

18 Main Street, Millerton, NY 12546
518.789.6630

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.

BARBARO

3279 Franklin Avenue, Millbrook, NY 12545
845.677.4440
BarbaroMillbrook.com

Neapolitan-style pizzas fresh out of the pizzaiolo and crafted cocktails in a warm, intimate setting.