Winchester, Massachusetts is home to a plethora of delectable dining options, but if you’re new to the area, choosing can be a challenge. Luckily, our team of Boston locals has been living and working in and around Winchester for many years, so we know a thing or two about where to find great food. From upscale restaurants to casual cafes, there’s something for everyone to enjoy.

Whether you’re looking for a romantic dinner for two or a fun night out with friends, we’ve got you covered with our top picks for the best places to eat in Winchester. So, grab a fork and get ready to explore some of the tastiest spots in town!  Here’s our list of some of the best restaurants our town has to offer.

A Tavola

Lovers of Italian food made from fresh, local ingredients will adore A Tavola. Their eclectic menu features a variety of small plates and entrees, including mouth-watering porchetta and several types of hand-made pastas.

Black Horse Tavern

Winchester’s premier tavern features a blend of casual tavern food, drink and specialty dishes. Located just steps from the Winchester Center commuter rail stop, the Black Horse Tavern is sure to provide an authentic pub dining experience.

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First House Pub

For tasty pub food in a casual atmosphere, First House Pub is our top choice. Their menu includes staples such as wings, burgers, and flatbread pizzas, but their dinner entrees are a cut above the rest. They also offer an impressive draught list, with over 20 beers always on tap.

Ristorante Lucia

Lucia’s is an authentic Italian restaurant with a charming, old-world-style atmosphere. Their generous menu offers a wide selection of dishes, including favorites like fried calamari and chicken parmesan. A local favorite, this welcoming restaurant is an excellent choice for any occasion, from a family dinner to a night out.

China Sky

Specializing in both Chinese and Japanese fare, China Sky offers an impressive menu featuring everything from General Tso’s Chicken to sushi and sashimi. Whether you’re in the mood to enjoy a sit-down meal or just call in some take-out, China Sky won’t disappoint.

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Cafe Nero

Another fantastic cafe located in Winchester center, Cafe Nero is a great place for coffee lovers and foodie enthusiasts alike. If you’re looking for a place to meet for a coffee or do a bit of work, Cafe Nero is a great option to check out.

Eleni’s Mediterranean Grille

Eleni’s serves delicious, healthy Mediterranean food made from fresh ingredients. Known for their Souvlaki, Wraps, Salads and more, they are conveniently located in Winchester center.

D’Agostinos Deli

Whether you’re looking for premade meals for the family, one of their signature Italian subs or artisan food and beverages, D’Agostinos is a go-to spot for Winchester residents and is a must try.

No matter what kind of cuisine strikes your fancy, you’re bound to find it here in Winchester. If you’re considering relocating to the Greater Boston area, Andersen Group Realty’s highly knowledgeable team of luxury real estate experts would love to hear from you. To learn why we’re North of Boston’s top real estate professionals, contact us today.