Shopping in the Berkshires: A Guide to the Best Stores, Boutiques and Shops—With The Red Lion Inn as Your Hub

Township Four at The Red lion inn

Nestled in the picturesque hills of western Massachusetts, the Berkshires is a haven for art lovers and nature enthusiasts … but also shoppers! Using the iconic Red Lion Inn in Stockbridge as your homebase, you'll find an array of high-end shops, antiques stores, and unique boutiques that capture the charm and sophistication of this beautiful region. Here's a guide to some of the best shopping in the Berkshires.

The Red Lion Inn, a historic landmark in Stockbridge, offers colonial charm, beautiful accommodations, and fine dining, making it an excellent base for shopping adventures. So, fuel up with a leisurely breakfast in the Main Dining Room, pop on some walking shoes, and get ready to explore the best shopping the Berkshires have to offer.

Stockbridge & West Stockbridge: Quintessential New England Charm

Start your shopping journey right in Stockbridge. The quaint downtown area boasts several must-visit shops:

• Williams & Sons Country Store

• Schantz Galleries

• Flourish Market

• Township Four

• Shop Around the Corner 

• Whispered the Heart

Lenox: Upscale Shopping with a Cultural Twist

A short drive from Stockbridge, Lenox is known for its cultural attractions, including Tanglewood and The Mount, but it also offers these high-end shops:

• Casablanca

• MacKimmie Co.

• The Gifted Child

• Design Menagerie

• Concepts of Art - Lenox Judaica 

Great Barrington: A Shopper’s Paradise

Great Barrington, considered one of the most charming small towns in America, offers loads of shopping options, mostly on the main drag: 

• Hammertown

• Sett & One Mercantile

• Asia Barong

• Familiar Trees 

• Fluff Alpaca 

• Scout 

• Lauren Clark Fine Art 

• Westerlind 

• Matrushka 

• Tom’s Toys 

Pittsfield: Historic Charm Meets Modern Elegance

Pittsfield, the largest town in the Berkshires, seamlessly blends historic charm with modern amenities:

• Museum Facsimiles Outlet Store

• Berkshire Emporium

• Paul Rich & Sons Home Furnishings

• The Plant Connector

• Dory & Ginger

Sheffield: Antiques and Artisanal Finds

Sheffield is renowned for its antique shops and artisanal boutiques:

• Berkshire Mountain Distillers

• Michael Wainwright USA

• La Trianon

Lee: Outlets and Boutiques

Lee offers a mix of high-end outlets and charming shops:

• Lee Premium Outlets

• Gallery315Home

• Retro Pop

The Berkshires offers a widely varied but very fun shopping experience, with each town providing its unique blend of high-end stores, boutiques, and galleries. Using The Red Lion Inn in Stockbridge as your hub, you can easily explore the best shopping destinations the region has to offer. Whether you’re seeking fine art, elegant fashion, or unique antiques, plan your next visit to the Berkshires for a shopping experience that delights every taste.