Wheatleigh

Charming locale with a warm interior dishing up traditional American eats & baked goods.

Pastry shop offering French and Berkshire-inspired items, including gluten-free options.

Explore the enchanting summer home of sculptor Daniel Chester French, where guided tours and stunning gardens showcase his iconic works.

Storied inn with nearby guesthouses offering turndown service, a heated pool & farm-to-table dining. Comprising a main building dating to 1773 and nearby guesthouses, this historic inn in the Berkshires is 0.7 miles from Stockbridge Golf Club. The antiques-furnished rooms and suites are individually decorated and offer free Wi-Fi, cable TV with DVD players, and turndown service. Some suites have whirlpool tubs and/or kitchens, and some guesthouses have gardens. Amenities include a fitness room, a heated pool and a hot tub. There's also a library and a sitting area in the main building, plus a farm-to-table restaurant and a pub with nightly entertainment acts. Meeting rooms are also available, and parking's free.

Nestled in Stockbridge, this charming museum showcases an extensive collection of Norman Rockwell’s iconic works, alongside beautiful grounds and contemporary exhibits.

Nestled in Harvard Square, this cozy converted greenhouse serves up New American cuisine and crafted cocktails, boasting a standout rooftop deck for al fresco vibes.

At Lincoln Tavern, get ready for a lively South Boston spot serving up modern American comfort food like fruity pebble pancakes and epic pizzas, plus craft cocktails in a bustling pub setting.

This quaint flea market, nestled in a drive-in lot, offers a mix of trinkets and treasures, with a casual vibe and food to snack on while you browse.

This chill Seaport gem serves up irresistible crepes and creative cocktails in a laid-back atmosphere, perfect for sunset views on the terrace.

Nestled in a charming house with a porch, this cozy café serves up fresh-baked breads, pastries, and hearty soups, making it a delightful stop for breakfast and lunch.