undefined Itinerary

Today, explore the historic downtown area of Stockbridge. Start with a visit to the Mission House, a historic house museum that tells the story of the town's early settlers. Then, head to the Stockbridge Library, Museum & Archives to learn about the town's rich literary history.

After lunch at the funky Once Upon a Table, take a scenic drive to the nearby town of Lenox. Here, you can visit the Mount, the former home of author Edith Wharton. The estate features beautiful gardens and a stunning mansion.

For dinner, try Alta Restaurant & Wine Bar, a cozy spot that offers contemporary American cuisine and an extensive wine list.

Today, get outdoors and explore the natural beauty of the Berkshires. Start with a hike in the nearby Kennedy Park, which offers miles of wooded trails and stunning views of the surrounding mountains.

After your hike, head to the Berkshire Museum in Pittsfield. The museum has a diverse collection of art, history, and natural science exhibits that will appeal to all ages.

For dinner, try the Nudel Restaurant, a farm-to-table restaurant that focuses on local, seasonal ingredients and offers an ever-changing menu of creative dishes.

Start your day with a visit to the Chesterwood Estate, the former home of sculptor Daniel Chester French. The estate features beautiful gardens and a museum that showcases French's work.

After lunch at the Main Street Cafe, head to the nearby town of Great Barrington. Here, you can explore the shops and galleries on Main Street, or visit the Mahaiwe Performing Arts Center, which hosts a variety of concerts and shows.

For dinner, try the Prairie Whale, a cozy restaurant that focuses on local, sustainable ingredients and offers creative, seasonal dishes.

On your last day in Stockbridge, take a scenic drive to the nearby town of Lee. Here, you can visit the Lee Premium Outlets for some shopping, or head to the nearby October Mountain State Forest for a hike or picnic.

After your morning activities, head back to Stockbridge for a visit to the Schantz Galleries, which specialize in contemporary glass art.

For your final dinner in Stockbridge, try the cozy and romantic Wheatleigh hotel, which offers gourmet cuisine and an extensive wine list in a beautiful setting.