New Lebanon, NY:

Mario’s Restaurant – Classic Italian-American eatery with hearty portions (Dinner, $$)

Lenox, MA:

Cello – Cozy bistro with a focus on Mediterranean flavors and fine wine (Dinner, $$$)

Alta Wine Bar – Elegant spot for wine and small plates, Mediterranean-inspired (Dinner, $$$)

Brava – Tapas and craft beer/wine bar with a lively atmosphere (Dinner, $$)

Boema Pizzeria – Artisan wood-fired pizzas with gourmet toppings (Lunch/Dinner, $$)

Café Triskele – French bistro with a seasonal menu and charming ambiance (Dinner, $$$)

Frankie’s – Modern Italian with handmade pasta and an extensive wine list (Dinner, $$-$$$)

Pittsfield, MA:

Sibaritas Italian – Family-friendly Italian fare with homemade pasta (Dinner, $$)

Old Man Jeff’s BBQ– Laid-back barbecue joint with smoked meats and sides (Lunch/Dinner, $$)

Thrive Diner – Vegan and health-conscious diner with plant-based comfort food (Breakfast/Lunch/Dinner, $$)

District Kitchen and Bar – Modern American gastropub with craft cocktails (Dinner, $$$)

Woodlife Farmers Market– Gourmet market with fresh, local bites and baked goods.

Haven Café and Bakery – Casual brunch/lunch spot with fresh pastries and coffee.

Blueberry Hill Cafe – Cozy breakfast and brunch café with comfort food.

All great for breakfast and lunch!

October Mountain State Forest – The largest state forest in Massachusetts, offering scenic trails for all levels, dense woodlands, and great spots for wildlife watching, camping, and fishing.

Pleasant Valley Audubon Wildlife Sanctuary – A peaceful nature sanctuary with well-maintained trails, a beaver pond, and stunning views of Lenox Mountain. Great for birdwatching and spotting local wildlife.

More general information about hiking trails in the Berkshires and Lenox.

The Mount – Edith Wharton’s Home – The historic home of Pulitzer Prize-winning author Edith Wharton, featuring beautiful gardens, guided tours, and literary events.

Hancock Shaker Village – A living history museum showcasing Shaker life, with preserved buildings, working farms, and artisan demonstrations.

Tanglewood– The summer home of the Boston Symphony Orchestra, offering world-class classical, jazz, and contemporary concerts in a stunning outdoor setting.

TurnPark Art Space – An outdoor sculpture park and gallery combining contemporary art, architecture, and nature in a unique creative space.

TurnPark Art Space – An outdoor sculpture park and gallery combining contemporary art, architecture, and nature in a unique creative space.

Berkshire Opera Festival – A premier opera company presenting high-quality productions and performances featuring renowned and emerging artists.

Clark Art Institute – A world-class art museum featuring European and American masterpieces, beautiful grounds, and rotating exhibitions.

Norman Rockwell Museum – A must-visit museum dedicated to the iconic American illustrator, showcasing his famous Saturday Evening Post covers and other works.

MASS MoCA – One of the largest contemporary art museums in the country, featuring cutting-edge exhibitions, immersive installations, and live performances.

Naumkeag – Choate Home – A beautifully preserved Gilded Age mansion with stunning gardens, offering tours and seasonal events.

Shakespeare & Company – A renowned theater company presenting Shakespearean and contemporary plays in an intimate, immersive setting.

Canyon Ranch

 Miraval Resort and Spa