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When you visit this quintessentially New England town, there is no shortage of sights and flavors to enjoy.


A longtime Winchester institution for a reason, Lucia exemplifies classically elegant Italian dining. 13 Mount Vernon St., 781-729-0515,

A Tavola
Pasta made fresh every day anchors a menu of impeccably executed Italian classics, served up in a warm and elegant atmosphere. 34 Church St., 781-729-1040,

Gingerbread Construction Co.
When a run-of-the-mill muffin won’t do, stop in for an indulgent creation like the buttercream-stuffed Chocolate Dreme or the lemon poppy seed muffin, swirled with citrus curd. 562 Washington St., 781-729-7700,

Explore new flavors with a visit to this Nepalese eatery that offers healthy and unique curries, stir-fries, and dumplings. 831 Main St., 781-369-1477,

Black Horse Tavern
Following in the footsteps of a historical tavern of the same name, the Black Horse aims to be a pub where the community can gather for conversation and good food—and succeeds. 32 Waterfield Rd., 781-369-1620,


Book Ends
Quintessentially quaint, Book Ends invites you to pick up the latest bestsellers or browse lesser-known volumes to find your next favorite author. 559 Main St., 781-721-5933,

House of Hot Sauce and More
Tabasco too tame? Visit the House of Hot Sauce for tongue-searing condiments, as well as jerky, spicy snacks, and bold seasonings. 7 Winchester Terrace, 978-848-2121,

The Branch Olive Oil & Spices
Add some flair to your pantry with infused olive oils (spicy Tuscan herb, perhaps), flavored balsamic vinegars (try the blackberry ginger), and other gourmet treats. 3 Thompson St., 781-365-8870,

Mahoney’s Garden Center
From a greenhouse stuffed with houseplants to an exhaustive inventory of gardening supplies, Mahoney’s is a sensory delight for anyone with even the slightest green thumb. 242 Cambridge St., 781-729-5900,

Find the perfect one-of-a-kind clothing, jewelry, and gifts at this boutique that is always curated with creativity and style. 6 Mount Vernon St., 781-570-2117

Studio on the Common | Photograph by Doug Levy

Studio on the Common
Community, creativity, and connection are the goals here. You can shop for gifts and cards, or sign up for a night of painting or crafts. 22 Church St., 781-721-1023,


Middlesex Fells Reservation
Access 2,200 acres of wilderness in the heart of suburbia and ramble through woodlands, wetlands, and rugged hills. South Border Rd., 781-662-2340,

Middlesex Fells Reservation

Griffin Museum of Photography
A small art museum dedicated to photography, this downtown institution features exhibits by accomplished photographers and emerging artists, as well as educational opportunities for aspiring amateurs. 67 Shore Rd., 781-729-1158,

Wright-Locke Farm
Shop for certified organic fruits and vegetables, visit with goats and chickens, learn more about local agriculture, and stroll the hiking paths that loop around the acreage at this nearly 400-year-old farm property. 78 Ridge St.,