Eating Up Boston’s History

Historic restaurants along Boston’s Freedom Trail where you can dine like our forefathers

If you’re planning a holiday to Boston, chances are you’ll find yourself pounding the pavement or, more likely, contending with scraggy cobblestones, along The Freedom Trail, a popular tourist attraction that may be familiar to you. Winding through the heart of the city, the 2.5-mile, self-guided trek connects 16 sites of historic importance—most centered on the Revolutionary War era—via a red-painted line on ground. Walking it was one of my first jobs on the job here at Where. I found that this mobile adventure into the past sapped up a lot of energy, so you’ll probably need some nourishment along the way, too. And with that, we’ve got restaurants en route that serve up delectable eats as well as striking biographies of their own:

Parker’s RestaurantSteps from King’s Chapel Burying Ground stands Parker’s Restaurant, the birthplace of Boston Cream Pie—so if you’re going to try the iconic dessert while you’re in town, you must do it here. Also of note, both culinary and cultural personalities have worked in the kitchen, including Emeril Lagasse, bam!, as sous-chef, Vietnamese Communist leader Ho Chi Minh as a baker, and African-American activist Malcolm X as a busboy. 60 School St., 617.227.8600

Parker's Restaurant dining room (Courtesy of Omni Parker House)

Union Oyster House—Opened in 1826, Union Oyster House, with its gold-scripted signage and glowing, wide-paned windows, is the nation’s oldest, continuously operating restaurant. It was here in the 1770s where Isaiah Thomas printed his weekly pro-Patriot political rag The Massachusetts Spy, and where Ebenezer Hancock paid out wages to the Continental Army. During a period of exile at the turn of the 19th century, France’s last ruling king, Louis Philippe I, lived in the upstairs apartment and tutored young ladies in French. Once a restaurant, it became a local favorite for its fresh shellfish. Daniel Webster never missed a meal of brandy and oysters at the bar; later, John F. Kennedy patronized the spot and still has a booth reserved in the upstairs dining room. A stone’s throw from Faneuil Hall; try the oysters, of course! 41 Union St., 617.227.2750

(©Union Oyster House)

Chipotle Mexican Grill—Yes, you’re reading that right. We are talking about the international fast-casual burrito chain, but we can’t forgo a mention in this piece thanks to its supremely historic location in Old Corner Book Store. First an apothecary, the charming brick building is famous for its role as an early-19th-century bookstore and printing shop, frequented by its publishing authors Longfellow, Alcott, Hawthorne, Emerson, Oliver Wendell Holmes and Harriet Beecher Stowe. 283 Washington St., 617.939.0988

The Old Corner Book Store was a famed literary destination; today you can get a quick burrito. (Courtesy Boston Public Library)

Durgin-Park—Ready to dig into Yankee fare, from baked beans to broiled scrod, pot roast and Indian pudding? Do it here. Durgin-Park is Boston’s “other” traditional restaurant, and like its compatriot, Union Oyster House, opened circa 1826. It began as a small dining hall in Peter Faneuil’s market house, catering to sailors and merchants (at the time, Boston Harbor lapped at its doorstep) as far back as 1742. Today, it still serves over-sized cuts of prime rib in one of the city’s most visited destinations, Faneuil Hall Marketplace. North Market building, 617.227.2038

Durgin Park sign


Warren TavernWarren Tavern in Charlestown, at the end of The Freedom Trail near Bunker Hill Monument and Old Ironsides, the USS Constitution, has been around since 1780 and once counted Paul Revere as a regular and George Washington as a customer. Stop here for the amazing house-made potato chips in the state's oldest tavern. 2 Pleasant St., 617.241.8142

The oldest tavern in the state (Photo courtesy

Chart House—From Faneuil Hall Marketplace, venture down State Street a few hundred yards to Long Wharf, where, in the 18th century, large trade ships would anchor and unload their goods. One structure, called the Gardiner Building, remains, and it is now the Chart House restaurant, although John Hancock famously used it as his offices and counting house. Check out Hancock’s original safe and then have fresh lobster cracked tableside. 60 Long Wharf, 617.227.1576

Chart House