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Downtown Winchester is about as representative of New England as you can get. The main streets wind past brick storefronts that are home to locally owned small businesses: an independent bookstore, florists’ shops, cafés. Walking paths circle an historic pond, and a white church steeple towers over it all. 

However, for all the town’s old-fashioned charm, it is also constantly evolving, maintaining its appeal as a great town to live in or visit. In recent years, the food scene has blossomed, with new eateries and gourmet shops joining the existing roster of favorite restaurants and cafés. 

“It has changed dramatically,” says Dana Garmey, associate director of the Winchester Chamber of Commerce and a longtime resident of the town. “We have so many options now, which is amazing.”

Making the dining scene even more appealing, she says, are Winchester’s compact, walkable downtown and picturesque surroundings. Plentiful parking makes it easy to drive in and stroll the area, window-shopping or browsing menus before settling in for a meal. And, since the onset of the COVID pandemic, many of the eateries have spilled out onto the sidewalk, adding to the convivial charm.

“Most of the restaurants have outdoor dining,” Garmey says. “And here in Winchester, you’re sitting on historic, beautiful cobblestone streets.”

The most venerable of Winchester’s dining institutions is undoubtedly Lucia Ristorante, which has been serving up classic Italian cuisine in the heart of town since 1985. The restaurant was founded by Filippo Frattaroli, who came to the United States from Italy when he was just 16. This heritage is evident in the menu, which focuses on authentic Italian offerings and incorporates many ingredients imported from Italy, including truffled olive oil from a family farm in the Abruzzo region. 

Customers particularly clamor for the Lucia lasagna, one of the few red-sauce dishes available, as well as the scaloppine Abruzzese, in which veal and chicken are sautéed with butter, white wine, and broccoli, then tossed with penne and cheese. The maccheroni amatriciana—homemade spaghetti chitarra topped with pancetta, pecorino, red pepper flakes, onion, and crushed tomato—is another favorite. 

Lucia Ristorante | Photograph by Brian DeMello

“What sets us apart from most restaurants is the tie we have to Italy,” says Philip Frattaroli, the son of the founder and now a co-owner. “It’s not an Italian-American restaurant—it’s an Italian restaurant.” 

While Lucia is an institution in town, it is also evolving. The owners are building a bakery-café elsewhere in Winchester that will operate as a casual retail café, as well as producing all of the bread, pasta, and desserts for Lucia in Winchester and its sister restaurant of the same name in Boston.

For another Italian option, head around the corner to A Tavola, where you might order the swordfish with creamy polenta, kale, and olive oil-poached heirloom tomatoes or the tagliatelle bolognese. Sourdough bread made daily, seasonal cocktails, and locally sourced produce round out the experience. 

If you’re more interested in a burgers-and-beer vibe, check out The Black Horse Tavern or the First House Pub (or both). Both offer plenty of beers on draft, an array of creative burgers, and pub fare standards alongside a few less obvious choices, like the Black Horse’s blackened swordfish tacos or First House’s prosciutto and fig flatbread. 

Griffin Museum of Photography | Photograph by Jared Charney

There are also abundant choices for an afternoon snack or a lighter meal. The newly opened Playa Bowls offers an indulgent assortment of smoothies, açaí bowls, and other plant-based bowls. At longtime favorite, the Gingerbread Construction Company, you can make your sweet tooth happy with muffins ranging from the conventional—fruit-loaded blueberry—to the decadent, the doubly chocolatey Chocolate Dreme muffin. 

But you don’t have to dine out to enjoy the culinary offerings of Winchester. Make a visit to Wright-Locke Farm, where you can visit with the farm animals or stroll through the woods and then stock up on organic produce, pasture-raised meats, locally made baked goods, and prepared foods from local purveyors. Find the finishing flavors for your meal at House of Hot Sauce and More or The Branch Olive Oil and Spices. 

When you’re done eating (or maybe just between stops), you could browse the gift shops and boutiques that dot the downtown or pay a visit to the Griffin Museum of Photography. Then take a stroll around Mill Pond in the adjacent park, taking in the postcard-perfect views.

Then it might be time to head home. Unless, of course, you have room for dessert.  

For more ideas how to spend a day in Winchester, visit our list of must-do destinations.