Massachusetts is a state steeped in history, with its cobblestone streets, colonial architecture, and countless landmarks that tell the story of America’s beginnings. But history isn’t confined to museums and monuments here; it’s also alive in the state’s dining scene. From taverns that have stood the test of time to restaurants housed in historic buildings, these dining spots offer more than just a meal—they provide a taste of the past. Here are some of the best historic restaurants in Massachusetts where you can dine while soaking in the rich history of the area.
1. Union Oyster House (Boston)
As the oldest continuously operating restaurant in the United States, Union Oyster House in Boston is a living piece of history. Established in 1826, this iconic eatery has welcomed everyone from statesmen to celebrities, all while serving up some of the best seafood in the city. The restaurant’s interior retains much of its original charm, with dark wood paneling, cozy booths, and memorabilia that hark back to its early days.
Dining at Union Oyster House is like stepping back in time. Signature dishes include the classic New England clam chowder, fresh oysters shucked to order, and the famous Boston baked beans. Located near the Freedom Trail, it’s the perfect spot to immerse yourself in Boston’s history while enjoying a delicious meal.
2. The Warren Tavern (Charlestown)
Located in Charlestown, just a short walk from the Bunker Hill Monument, The Warren Tavern is one of the oldest and most historic pubs in the country. Established in 1780, this tavern has hosted the likes of George Washington and Paul Revere. The building itself, with its low ceilings, wooden beams, and brick hearths, gives diners a genuine sense of what it was like to gather in a colonial-era tavern.
The Warren Tavern’s menu offers classic pub fare with a New England twist, including hearty dishes like shepherd’s pie, fish and chips, and clam chowder. With its rich history and warm, welcoming atmosphere, dining at The Warren Tavern is a must for anyone interested in the early days of America.
3. Parker’s Restaurant (Boston)
Housed within the Omni Parker House Hotel in downtown Boston, Parker’s Restaurant is another historic gem. The restaurant is famous for being the birthplace of the Boston cream pie and Parker House rolls, but its history goes much deeper. Opened in 1855, Parker’s Restaurant has seen the likes of literary giants like Charles Dickens and Ralph Waldo Emerson, and it was here that John F. Kennedy proposed to Jacqueline Bouvier.
The opulent decor, featuring crystal chandeliers, mahogany paneling, and gilded mirrors, transports you to a bygone era of elegance and refinement. The menu offers a blend of contemporary and classic New England cuisine, making it a perfect spot for a historic dining experience in the heart of Boston.
4. Longfellow’s Wayside Inn (Sudbury)
For those willing to venture a bit outside of Boston, Longfellow’s Wayside Inn in Sudbury offers a truly unique dining experience. Established in 1716, it’s the oldest operating inn in the United States. The inn became famous after being immortalized in Henry Wadsworth Longfellow’s “Tales of a Wayside Inn,” and it continues to exude the charm and hospitality of the colonial era.
The restaurant serves traditional New England fare, with dishes like roasted turkey, prime rib, and Indian pudding. Each dining room is named after a character from Longfellow’s tales, and the old-world decor, including fireplaces and antique furnishings, adds to the historic ambiance. Whether you’re stopping by for lunch, dinner, or a weekend getaway, Longfellow’s Wayside Inn is a true piece of living history.
5. The Red Lion Inn (Stockbridge)
In the heart of the Berkshires, The Red Lion Inn has been welcoming guests since 1773. This historic inn and restaurant have become a symbol of New England’s storied past, offering a cozy and inviting atmosphere that’s perfect for a meal steeped in history. The dining room, with its colonial decor and white tablecloths, provides a classic setting for enjoying seasonal dishes made with local ingredients.
Menu highlights include New England staples like clam chowder, roast duckling, and cider-braised pork. After your meal, take some time to explore the inn’s quaint surroundings or relax in one of its many lounges. The Red Lion Inn offers a dining experience that’s as much about the setting as it is about the food.
6. Umbria Boston
While not as old as some of the other establishments on this list, Umbria in Boston’s North End brings its own historical flavor to the dining scene. The restaurant occupies a space in one of Boston’s most historic neighborhoods, known for its rich Italian heritage and cobblestone streets. Umbria’s menu offers a modern take on classic Italian dishes, but it’s the ambiance and location that make it a standout.
With its rustic decor and views of the old streets of the North End, dining at Umbria allows you to feel connected to Boston’s storied past. Whether you’re enjoying handmade pasta, fresh seafood, or a glass of wine, Umbria offers a dining experience that combines the best of history and modern cuisine.
Dining at these historic restaurants in Massachusetts is more than just a meal—it’s a journey through time. From the colonial-era charm of The Warren Tavern to the literary legacy of Parker’s Restaurant, each of these establishments offers a unique way to experience the state’s rich history. Whether you’re a local or just visiting, make sure to add these historic dining spots to your itinerary. Not only will you enjoy delicious food, but you’ll also leave with a deeper appreciation for the stories and traditions that have shaped Massachusetts.