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Winchester often comes as a surprise to those experiencing it for the first time. The town sits just eight miles north of Boston, nestled between the bustling suburbs of Woburn, Malden, Medford, and Arlington. Yet, in the middle of all this activity, Winchester retains a small-town charm, community feeling, and—for the past few years—culinary cred that come as an unexpected delight to new visitors.

 

Middlesex Fells Reservation 

 

“It’s sort of a quintessential New England town,” says Judy Manzo, owner of local bookshop Book Ends and former president of the Winchester Chamber of Commerce. “It’s really a hidden gem.”

The area known today as Winchester was first settled by Europeans in 1640. It was originally named Waterfield, a nod to the many ponds, rivers, and streams in the area. More than 200 years later, the village—then called South Woburn—decided to incorporate as its own town, and today’s Winchester was born.

 

Lucia Ristorante

 

While many New England town centers evolved organically over the centuries, downtown Winchester was largely purpose-built to be—and look like—the town’s civic center. In the late 1800s, the stately brick town hall was constructed, to be joined a few years later by the Romanesque Winchester Savings Bank building. In 1931, the granite-faced public library joined the downtown. From these anchors stretch rows of brick-fronted shops and eateries, and the compact town center is surrounded by graceful residential neighborhoods, making Winchester an eminently walkable community.

 

 

Still, the town has seen some changes, particularly over the past decade, as changes to the town’s liquor licensing regulations have attracted more restaurants to town, helping turn Winchester into something of an unsung foodie haven. “In the last five-plus years, a lot of places have opened up,” says Craig Rabe, president of the Winchester Chamber of Commerce. “We don’t have to go into the city as much now.”

 

Wright Locke Farm

 

The elder mainstay of the Winchester dining scene is Lucia Ristorante, a beloved local institution with a sister restaurant in Boston’s North End. For more than 30 years, Lucia has served classic Italian dishes inspired by the owners’ home region of Abruzzo.

Think shellfish and marinara tossed with house-made pappardelle, or veal topped
with mozzarella and fried sage in a white wine sauce.

 

The Black Horse Tavern

 

Joining the scene in 2011 was A Tavola, the creation of Winchester resident and restaurateur Vittorio Ettore, who is also behind Medford’s acclaimed Bistro 5. With seasonally inspired dishes and creative, contemporary takes on pasta, flatbread, and piattini (Italian small plates), the restaurant is an excellent complement to Lucia’s Old World take on Italian dining.

A few casual restaurants have also joined these mainstays. The Black Horse Tavern, in operation for eight years, takes its name from a colonial-era gathering place. With local beer on tap, pub fare favorites on the menu, and games on the TV, the modern-day Black Horse recreates the community spirit of its predecessor.

 

Gingerbread Construction Company

 

The Waterfield Kitchen, opened in 2015, is part of the Serenitee group, which operates acclaimed eateries across the North Shore. The menu features sushi, savory small plates, and modern takes on comforting classics: apple-bacon meatloaf with caramelized onion jus, for example, or short ribs with apple and mustard seed marmalade.

Right from the beginning, Winchester was a clear fit for a Serenitee restaurant, says owner Mark McDonough. “The towns that we do best in are hometowns, community towns, where people know each other and like to meet up at the restaurant,” he says. “I see that quite a bit in Winchester.”

 

A Tavola

 

Visitors looking for a more casual snack or light meal can try Mamadou’s Artisan Bakery for French-style baked goods, the Gingerbread Construction Company for decadent muffins, or Nourish Your Soul for cold-pressed juices and vegan smoothies. Home cooks can find local produce and eggs at Wright-Locke Farm, and prepared delicacies at Pairings Wine and Food.

The compact, walkable community encompassing restaurants, shops, and residential areas is something many new mixed-use developments strive for, Manzo points out. But it is simply a fact of life in Winchester. “We just have it,” she says. “We’ve had it for over 100 years.”

 

Winchester Interary

 

Explore

Griffin Museum of Photography Completely dedicated to photography, this small museum features work by notable names and emerging artists, as well as talks, film screenings, and mentoring events for aspiring photographers. 67 Shore Rd., 781-729-1158, griffinmuseum.org

Middlesex Fells Reservation Access more than 100 miles of trails and ramble through 2,000-plus acres of scenic woods, enjoying birdsong and glorious foliage as you explore. South Border Rd., 781-662-2340, friendsofthefells.org

Wright-Locke Farm On this 20-acre historic property you can explore a working farm operation, feed chickens and goats, buy local organic produce, or hike the trails. 78 Ridge St., wlfarm.org

Mill Pond Stroll the path that runs behind town hall and the public library to enjoy the peace of the tree-lined pond and the beauty of the cascades.

Studio on the Common Part art education studio and part gift shop, this is the spot to indulge your creative side or shop for greeting cards, wedding and baby presents, and home accessories, all sourced from socially responsible vendors. 22 Church St., 781-721-1023, studioonthecommon.wildapricot.org

 

Dine

A Tavola If you’re craving cured duck breast, grilled flatbread topped with seasonal produce, or house-made pastas, try this casual sister restaurant of Medford’s acclaimed Bistro 5. 34 Church St., 781-729-1040, atavolawinchester.com

The Waterfield Kitchen Stop into this Winchester offering from the Serenitee restaurant group for award-winning sushi, elevated comfort food, and creative cocktails. 14 Thompson St., 781-729-0204, twk-winchester.com

Gingerbread Construction Company The indulgent muffins here could put any donut to shame. Try the cream-and-berry-stuffed Strawberry Shortcake Muffin or the buttercream-slathered Chocolate Dreme. 562 Washington St., 781-729-7700, gingerbreadusa.com

Lucia Ristorante Handmade pastas, cheeses, and truffles imported straight from Italy, plus traditional dishes, make this a destination for lovers of Italian dining. 13 Mount Vernon St., 781-729-0515, luciaw.in

Pairings Wine and Food Wine, cheese, charcuterie, and other treats are organized by style, so shoppers can learn as they browse and easily bring home perfectly matched pairings. 600 Main St., 781-721-9463, pairingswineandfood.com

Mamadou’s Artisan Bakery Look past the modest storefront and you will find artisan baguettes, rich brioches, and croissants that will make you dream of Paris. 63 Swanton St., 781-729-2600

 

Shop

Revel Lose yourself in this boutique and gift shop’s fun and unique collection of clothes, jewelry, bags, and housewares. 6 Mount Vernon St., 781-570-2117

Sole Amour Stop into this downtown boutique for a unique curated selection of shoes, bags, stylish clothing, and jewelry. 17 Thompson St., 781-721-5300, soleamour.com

Book Ends Peruse bestsellers, discover local authors, or catch a reading and book signing at this thriving independent bookstore. 559 Main St., 781-721-5933, bookendswinchester.com

Home Visit this eclectic shop for whimsical housewares, gourmet pet treats, and an array of charming gifts. 2A Mount Vernon St., 781-491-6130, home-winchester.com

Runway Couture is a shop not to be missed. The latest looks for women will have you coming back for more. 38 Church St., 781-721-7302

 

Winchester Information

Date of Settlement

1640

Date of Incorporation

1850

Population

22,491

Zip Code

01890

Median Household Income

$149,321

Schools

Ambrose Elementary School, Lincoln Elementary School, Lynch Elementary School, Muraco Elementary School, Vinson-Owen Elementary School, McCall Middle School, Winchester High School

Notable residents

Anchorwoman Kim Khazei, Olympian Alicia Sacramone, professional wrestler Kofi Kingston, Boston Bruins coach and general manager Harry Sinden, classical clarinetist Richard Stoltzman