As the Seasons Change, so Too Does Main Street

Not only is Winchester a wonderful place to live and work, but it also has a great mix of city and country, coupled with a walkable downtown, storefront opportunities, and a diverse restaurant scene.

Artisans & Crafters •  Diverse Restaurants • YMCA • Museums • Annual Festivals • Pet Parades • Hiking Trails • Breweries • Retro Art Deco Movie House • Whiting Mills • Outdoor & Indoor Recreation • Highland Lake GoCarts • American Museum of Tort Law • Ice Cream • Natural Wonders • American Mural Project • Miniature Golf • Duckpin Bowling • Largest Civil War Collection in the State • Antique Shops •  Community College • Old Mills • 6-lane, 25-meter Indoor Pool • Summer Concerts on the Green • Galleries • Sue Grossman Still River Greenway • Tiffany Windows • Hayrides on Main Street • ​New Deal/W.P.A. Art Mural • ​Solomon Rockwell House • ​​Skiing/Snowboarding, Wired Shared WorkSpaces and so much more!​

This Spring, come downtown and see what's new on Main Street!

Plant Life Aficionado: 60 Main Street, a humble, family owned Plant Shop with dreams of propagating nature's beauty and healing for all to enjoy.

Hartford HealthCare HealthCenter: 80 South Main Street, the new home of the hospital’s Hungerford Emergency & Medical Care. The location also features a landing pad for a LIFE STAR medical transport helicopter.

LIVE.Boutique: 396 Main Street, Boutique clothing, beautifully crafted jewelry, accessories & personalized gifts.

Rooted Market: 390 Main Street, is a local, family owned Health Food Store offering a variety of natural and organic products. We feature natural alternatives to all your grocery and vitamin needs. We also offer health and beauty items, cleaning supplies, herbal and homeopathic remedies, gift items, and so much more.

Railway Cafe: 580 Main Street, Homestyle breakfast and lunch favorites, big fresh salads, lots of baked goods, specialty coffees and ice cream too. Opening April 15!

2nd Home Lounge: 524 Main Street, A relaxing environment to enjoy a local craft beer, or glass of wine from a local winery, with a creative bite to eat with friends. Opening Soon!