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Romantic dining in Massachusetts ranges from dark & cozy restaurants to urban & hip

Romantic dining can be expressed in many kinds of restaurants, from a small, quiet traditional inn to a chic, hip restaurant on top of an urban skyscraper to a waterfront table. Massachusetts has them all.

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The Courtyard - Red Lion Inn - Stockbridge, MA
Red Lion Inn

30 Main Street Stockbridge, MA, 01262 Phone: 413-298-5545

Dining is an enchanting experience at this historic inn in the heart of the Berkshires

Everything about the Red Lion Inn is enchanting, but that is especially true when it comes to dining. The Main Dining Room is romance personified: You’re surrounded by soft candlelight and crystal chandeliers; antique china and colonial pewter on the tablecloths. It’s like going back to dining in the Gilded Age. The restaurant features traditional favorites and contemporary interpretations of classic New England cuisine, with a wine list that is a perennial recipient of the Wine Spectator’s Award of Excellence. For cozier dining, there’s the rustic Widow Bingham’s Tavern. And in the warmer months, you can dine al fresco under red umbrellas in a flower-filled courtyard. Don’t forget an after-dinner cocktail on the porch as evening settles over the charming village.

Visit our sister properties - Briarcliff - Porches Inn
Greater Boston is your Hub for Winter Wonder! Click here to explore.