Dine, Shop & Explore

Dine, Shop, Explore

If you’re tired of traffic and the suburbs, you will love your visit to Old Town. Come enjoy a wonderful meal on the Walking Mall; eat at an outdoor cafe and watch people stroll by or dine in a sumptuous dining room with a crackling fire. No matter the season or your dining preference, Old Town Winchester has something for you. And after your meal, visit our unique shops, enjoy a drink or an ice cream cone, stroll down shady streets, and enjoy the feeling of nostalgia here. It’s like coming home.

Tips for Visiting Downtown:


Share your favorite OTW photos in our #FriendsandFamilyOTW Contest

The Old Town Development Board has begun the first ever OTW Hashtag contest! Share what you love about Old Town Winchester through images posted to Instagram with the hashtag #FRIENDSANDFAMILYOTW. Three winners will be selected; a 1st, 2nd and 3rd prize will be awarded from gift certificates to downtown businesses. Each winning photo entry will also receive two OTW drinking glasses as well as an OTW tote bag. The contest starts now!

Take photos and share them on Instagram with the Hashtag #FriendsandFamilyOTW. Hashtag your images on Instagram from OTW; including selfies, food, purchases, architectural shots, and more! The image on Instagram with the most likes by January 31, 2018 will win the top prize. Second and third place prizes will also be awarded. OTW reserves the right to disqualify any photos not explicitly in OTW or not in the spirit of the competition. OTW reserves the rights to use the winning photos.

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