Tucked away in the Berkshires of Massachusetts sits Great Barrington—dotted with its postcard perfect brick-clad storefronts and circa 1905 theatre. For well over 100 years artists, writers and other creative types have turned the town into a four season destination where visitors and locals alike can enjoy hiking and skiing to its award-winning restaurant scene.

Featuring Andover Inn at Phillips Academy, Andover, Massachusetts, USA

Andover, Massachusetts, is a historic New England town known for its landscapes, charming downtown, and colonial heritage, evident in its well-preserved architecture. You can explore the Andover Historical Society and Addison Gallery of American Art. Andover offers scenic outdoor spaces and recreational activities, making it an inviting destination for both relaxation and cultural exploration.

Rockport, Massachusetts, is a coastal town known for its scenic beauty, featuring rocky beaches, quaint harbors, and iconic lobster traps. You can explore art galleries and boutiques along Bearskin Neck. Rockport's rich maritime history, highlighted by landmarks like Motif No. 1, and its peaceful ambiance make it a perfect destination for relaxation and exploration along the North Shore.

Rockport, Massachusetts, just 40 miles north of Boston, was settled in 1623 and made a name for itself with its abundant granite quarries, timber for shipbuilding and of course—one of the finest fishing grounds in New England.

Salem, Massachusetts, is famous for its history and association with the 1692 witch trials, offering unique attractions like the Salem Witch Museum. The town's charming streets are lined with preserved colonial architecture, boutique shops, and a vibrant arts scene. Salem's waterfront has numerous festivals, especially during Halloween, providing a lively atmosphere for visitors year-round.

Williamstown, Massachusetts, is a charming destination known for the renowned Williams College and the esteemed Clark Art Institute. Nestled in the Berkshires, it offers stunning natural landscapes perfect for outdoor activities like hiking and skiing. The town's vibrant arts scene, historical significance, and scenic beauty make it an ideal spot for a diverse and enriching getaway.