The Red Lion Inn: A Picturesque Getaway In The Berkshires

The Red Lion Inn, an iconic landmark located in picturesque Stockbridge, Massachusetts, represents some of the best lodging and dining in the Berkshires — perfect for all seasons, but offering a bit of magic in the winter. 

Unique character and charm present throughout the property. The main inn offers 82 rooms and suites that have each been individually decorated. There are also a handful of guest houses throughout the property. It transports you back in time — the authentic furniture, the artwork, the original lift. No two rooms are the same, but each will give you the feeling that by staying here you are a part of an even bigger history.

It all started in 1773 when the building was established as a small tavern and served as a stop for stagecoaches traveling between Albany and Boston. Much of the antique furniture and china found at the Inn today was from a Mrs. Plumb — the Plumbs purchased the Inn in 1873. Today, it’s owned by the Fitzpatrick family, and it’s been in their family since 1968. 

Rich history and old-world charm collide. Jack Fitzpatrick was a Senator in the Massachusetts State House. Jane Fitzpatrick, like Mrs. Plumb, was also a collector of objects and added hundreds of pieces to the Inn’s collection. Jane’s daughter, Nancy, and granddaughter, Sarah Eustis, now continue the tradition. It’s easy to get lost strolling the hallways of the Inn, admiring the pieces throughout. A Norman Rockwell phone booth (Stockbridge was home to Norman Rockwell and set the scene for many of his classic American paintings), a lion’s head on the wall, antique tea pots lining the windows of the restaurant — it all makes up the unique charm.

Throughout the centuries, guests have included five presidents — Cleveland, McKinley, Coolidge, both Roosevelts — as well as Nathaniel Hawthorne, William Cullen Bryant, John Wayne, Henry Wadsworth Longfellow, Thornton Wilder, and Bob Dylan. More recently, the inn has seen the likes of Steve Martin, Martin Short, Lyle Lovett, and Post Malone.

The restaurant at Red Lion Inn, helmed by Executive Chef Jon Sterrett, is a wonderful spot for a modern take on American classics, open for breakfast, lunch, and dinner (served on the Inn’s antique china, of course!). To start the day, breakfast allows you to indulge the way you should on vacation, with buttermilk pancakes, eggs Benedict, and don’t skip Nancy’s pastry basket for the table.

For dinner, you can’t go wrong with the bouillabaisse or the pan-seared black cod. For dessert, the Red Lion apple pie is really something special, and a perfect way to close out the all-American meal. 

The village of Stockbridge is small and quaint and we love the cafe culture that the village provides. There were multiple places to get a wonderful cup of coffee and pastry — like Stockbridge Coffee & Tea or The Lost Lamb. Also shop spots like Peace Love & Chocolate or Williams & Sons Country Store while you’re in town.

Jessica Mackin-Cipro

Co-Publisher/Editor

Jessica Mackin-Cipro is an editor and writer from the East End of Long Island. She has won numerous NYPA and PCLI awards for journalism and social media. She was previously the Executive Editor of The Independent Newspaper.

An East End Experience

2024 © James Lane Post®. All Rights Reserved.

Covering North Fork and Hamptons Events, Hamptons Arts, Hamptons Entertainment, Hamptons Dining, and Hamptons Real Estate. Hamptons Lifestyle Magazine with things to do in the Hamptons and the North Fork.